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Review

1,4-Diazatriphenylene and Its Hetero-Fused Analogs: Synthesis and Applications

by
Egor V. Verbitskiy
1,2,*,
Elizaveta M. Krynina
1,
Yuriy A. Kvashnin
1 and
Valery N. Charushin
1,2
1
I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, S. Kovalevskaya Str., 22, 620137 Ekaterinburg, Russia
2
Department of Organic and Biomolecular Chemistry, Ural Federal University, Mira St. 19, 620002 Ekaterinburg, Russia
*
Author to whom correspondence should be addressed.
Molecules 2026, 31(12), 2197; https://doi.org/10.3390/molecules31122197
Submission received: 19 May 2026 / Revised: 10 June 2026 / Accepted: 17 June 2026 / Published: 22 June 2026
(This article belongs to the Special Issue Advances in the Synthesis of Heterocyclic Compounds and Their Applications, 2nd Edition)
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Abstract

This review highlights the recent advances in the synthesis of 1,4-diazatriphenylenes and their various structural analogs. It focuses on several methodologies, including condensation reactions and intramolecular cyclizations of 2,3-di(het)aryl-substituted pyrazine derivatives. These methods exploit either oxidative photocyclization (the Mallory reaction), intramolecular cyclodehydrogenation (the Scholl reaction), or intramolecular SNH reactions (nucleophilic aromatic substitution of hydrogen) involving 2-bis(het)aryl-substituted 1,4-diazine derivatives. Additionally, the review explores the potential applications of these compounds as fluorescent and/or semiconducting materials in organic electronics, as well as their role in coordination chemistry and biological issues. It summarizes the literature from 2018 to March 2026, complementing the data discussed in our previous review.

1. Introduction

Over the past three decades, polycyclic aromatic hydrocarbons have gained widespread attention due to their use in materials chemistry, organic electronics, and the design of chemosensors and molecular probes for medical applications [1,2]. (Aza)triphenylenes are tetracyclic structures representing the smallest examples of benzenoid polycyclic aromatic hydrocarbons. (Aza)triphenylene derivatives have gained significant attention in supramolecular and heterocyclic chemistry due to their rigid, planar, and conjugated structures, as well as their self-assembling properties [3,4,5]. A remarkable compound in this area is 1,4-diazatriphenylene (also known as dibenzo[f,h]quinoxaline), along with its fused analogs. These polycyclic nitrogen-containing heteroaromatic compounds are characterized by fully conjugated frameworks that are enforced to be planar and exhibit threefold rotational symmetry. They have become the key building blocks in advanced materials chemistry. These structurally rigid systems demonstrate exceptional electron delocalization and supramolecular ordering, making them highly suitable for applications in optoelectronic devices, functional coordination polymers, and energy storage systems [3,4,5,6].
There are several key routes to construct the 1,4-diazatriphenylene scaffold, based on condensation reactions (Route 1) [4,5], intramolecular cyclizations of 2,3-di(het)aryl-substituted pyrazines using oxidative photocyclization (the Mallory reaction) [6,7] or intramolecular cyclodehydrogenation catalyzed by chemical oxidants under acidic conditions via the Scholl reaction (Route 2) [8,9], or intramolecular SNH reactions (nucleophilic aromatic substitution of hydrogen) of 2-bis(het)aryl-substituted 1,4-diazine derivatives (Route 3) [10,11] (Figure 1).
The most common method to obtain 1,4-diazatriphenylene derivatives is based on the condensation of 1,2-diamines with substituted phenanthrene-9,10-diones and their heteroanalogs (see Figure 1, Route 1). However, a significant limitation of this method is due to difficulties in obtaining and structural identification of asymmetric 1,4-diazatriphenylene derivatives when R1 ≠ R2 and R3 ≠ R4.
Due to their broad applications in various fields, continuous efforts are being made to develop new, convenient, and efficient synthetic approaches to a variety of 1,4-diazatriphenylene derivatives. Based on existing practices and relevant research areas, two comprehensive reviews, focusing on modern methods for synthesizing diazatriphenylenes, were published in 2017 and 2018 [4,5]. In this review article, we wish to discuss the topic by primarily examining the literature data published from 2018 to the present. Figure 2 illustrates the structures of various 1,4-diazatriphenylenes and their condensed analogs, which are covered in this review.

2. Synthesis Using Cyclocondensation Reactions

The first derivative of 1,4-diazatriphenylene, dibenzo[a,c]phenazine (3a), was synthesized in 1951 through the condensation of 9-nitrophenanthrene (1) with aniline (2) on heating without solvent at 170–180 °C in the presence of powdered NaOH as a catalyst (Scheme 1) [4].
As noted above, currently the most widespread method used for the synthesis of 1,4-diazatriphenylene derivatives and their fused analogs is the condensation of 1,2-dicarbonyl compounds, for example, derivatives of phenanthrene-9,10-dione (4), 1,10-phenanthroline-9,10-dione (5), or pyrene-4,5-dione (6) with the corresponding 1,2-diamines, such as derivatives of ethylenediamine (7, 8) and o-phenylenediamine (12–17) (Scheme 2). Reaction conditions for condensations leading to derivatives of dibenzo[a,c]phenazine (9), pyrazino[2,3-f][1,10]phenatroline (10), phenanthro[4,5-fgh]quinoxaline (11), dibenzo[f,h]quinoxaline (3, 18–21), pyrazino[2,3-f][1,10]phenatrolines (22–26) and phenanthro[4,5-fgh]quinoxalines (27, 28) are presented below (Scheme 2, Table 1 and Table 2).
A series of various [7]helicenes containing a 1,4-diazatriphenylene moiety (171–177) were synthesized by condensation of benzo[1,2-c:4,3-c′]diphenanthrene-9,10-dione (28) with ethylenediamine (7) and various aromatic diamines (12a, 12g, 12ah, 12ai, 15b, and 17) (Scheme 3) [182].
It is important to note that heteroanalogs of 1,4-diazatriphenylene can be obtained by condensation of 1,2-diketones with 1,2-diamines, proceeding under acidic conditions. This method has been used to obtain dithieno[3,2-f:2′,3′-h]quinoxalines and thieno[2′,3′:4,5]thieno[3,2-f]thieno-[2′,3′:4,5]thieno[2,3-h]quinoxalines [183,184,185]. Since 2018, a huge number of substituted heteroanalogs of 1,4-diazatriphenylenes (over a hundred compounds, obtained through this procedure) have been described [68,69,186,187,188,189,190,191,192,193,194,195,196,197,198,199,200,201,202,203,204,205,206,207,208,209,210,211,212,213,214,215,216,217,218,219,220,221,222,223,224,225,226,227,228,229,230,231,232,233,234,235,236,237,238,239,240,241,242,243,244,245,246,247,248,249,250,251,252,253,254,255,256,257,258,259,260,261,262,263,264,265,266,267].

3. Synthesis Using the Scholl Reaction

The Scholl reaction, nucleophilic aromatic substitution of hydrogen, or metal-catalyzed cross-coupling reactions are less common synthetic approaches for 1,4-diazatriphenylenes and their heteroanalogs.
For instance, 1,4-diazatriphenylene (9n) and some derivatives (3db and 3dc) were synthesized via the Scholl reaction from either 2,3,5,6-tetrasubstituted pyrazine (30) or 2,3-disubstituted quinoxalines (31 and 32), as illustrated in Scheme 4 [268,269].
2,2′-(4,5-Dinitro-1,2-phenylene)bis(9,10-dihydro-9,10-[1,2]benzoanthracene) (32) takes part in the Scholl reaction when treated with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and trifluoromethanesulfonic acid. The resulting polycyclic product (33) undergoes reduction of both nitro groups by action of hydrazine hydrate in the presence of palladium on carbon. This reduction yields the corresponding 1,2-diamino compound (34), which undergoes condensation with 2,7-di-tert-butylpyrene-4,5,9,10-tetraone (6p) to produce the desired 18,41-di-tert-butyl-5,8,13,23,28,31,36,46-octahydro-5,46:8,13:23,28:31,36-tetrakis([1,2]benzeno)heptapheno[7,8-i]-hepapheno[7″,8″:6′,7′]-quinoxalino[2′,3′:9,10]phenanthro[4,5-abc]phenazine (35) in 90% yield (Method A) (Scheme 5).
Conversely, if one starts with the dinitro derivative (32) and first reduces it into the corresponding 1,2-diamino compound, followed by condensation with the tetraoxo derivative (6p) of pyrene (6p) and then the Scholl reaction, the same polycyclic product (35) can be obtained, but in a significantly lower yield of 35% (Method B) (Scheme 5) [270].
A convenient synthetic approach to a variety of heteroanalogs of 1,4-diazatriphenylene is the sequential use of Scholl reactions and nucleophilic aromatic substitution of hydrogen.
For example, quinoxalines (38a,b) react with various thiophene derivatives and benzo[b]furan (39–42) in the presence of lithium 2,2,6,6,6-tetramethylpiperidine (TMPLi) (generated in situ during treatment of 2,2,6,6-tetramethylpiperidine (TMPH) with n-butyllithium) to afford symmetrical 2,3-di(het)aryl-substituted quinoxalines (44a–k). Derivatives 44b–k were then subjected to a Scholl reaction with [bis(trifluoroacetoxy)iodo]benzene (PIFA) in the presence of boron trifluoride etherate, thus affording heteroanalogs of 1,4-diazatriphenylene (45a–k) (Scheme 6) [271].
[1,2,5]Oxadiazolo[3,4-b]pyrazine derivatives have recently gained significant attention from researchers due to their potential as high-energy compounds and their promising applications in electronics and photovoltaics [272,273,274]. It has been demonstrated that 5-(het)aryl-substituted [1,2,5]oxadiazolo[3,4-b]pyrazines (46a–c) can undergo a Lewis acid-catalyzed nucleophilic aromatic substitution of hydrogen (the SNH reaction) with such C-nucleophiles as 2-hexyl-thiophene (47) and 1,3-dimethoxybenzene (48). This reaction leads to the formation of ortho-di(heteroaryl)-substituted [1,2,5]oxadiazolo[3,4-b]pyrazines (51–52) (Scheme 7) [275].
This synthetic approach was applied to synthesize more complicated derivatives, including substituted [1,2,5]oxadiazolo[3,4-b]pyrrolo[2,3-f]thienoquinoxalines (56a,b), [1,2,5]oxadiazolo[3′,4′:5,6]pyrazino[2,3-c]thienocarbazoles (57a,b), [1,2,5]oxadiazolo[3′,4′:5,6]pyrazino[2,3-c]indolo[2,3-a]carbazole (57c), and [1,2,5]oxadiazolo[3′,4′:2,3]thienoquinoxalino[6,5-b]carbazoles (58a,b), achieving yields of 32–88% (Scheme 8) [276].
5,6-Dihydrodiindolo[3,2-a:2′,3′-c]phenazine derivatives (61a–d) can be synthesized in a similar manner. The SNH reaction between quinoxalines (38a and 38c) and indoles (59a–c) yields 2,3-substituted 1,4-dihydroquinoxalines (60a–d), which are subsequently transformed via the Scholl reaction into polycycles 61a–d (Scheme 9) [277].
The Suzuki cross-coupling reaction can also be employed in the syntheses of diarylpyrazines, instead of the SNH reactions. This procedure involves the cross-coupling of 2,3-dibromopyrazines (62a,b) with arylboronic acids (63a–c), thus affording 2,3-(het)arylpyrazines (65a–d). These products can be converted further into 1,4-diazatriphenylene derivatives (66a–d) by using molybdenum(V) chloride, as illustrated in Scheme 10 [278].

4. Synthesis Using Photocyclization Reactions

Intramolecular cyclizations of 2,3-di(hetero)aryl-substituted pyrazine derivatives via oxidative photocyclization (the Mallory reaction) represent a convenient, albeit less common, method for the synthesis of heteroanalogs of 1,4-diazatriphenylenes.
For example, dithieno[2,3-f:3′,2′-h]quinoxalines (68a,b) were readily prepared in yields up to 60% via Royal Blue LED (450 nm) irradiation of 5,6-di(thiophen-2-yl)pyrazine-2,3-dicarbonitriles (67a,b) (Scheme 11) [279].
To enter the Mallory reaction, the compounds 6-R-2,3-di(thiophen-2-yl)-5H-pyrrolo[3,4-b]pyrazine-5,7(6H)-dione (69) and various 2,3-di(thiophen-3-yl)pyrazine derivatives (71–73) were exposed to UV irradiation in the presence of iodine as an oxidizing agent. This oxidative photocyclization resulted in the formation of dithieno[2,3-f:3′,2′-h]quinoxaline (70) and dithieno[3,2-f:2′,3′-h]quinoxaline (74–76) derivatives in yields reaching up to 69% (Scheme 12 and Scheme 13) [6,280].
Another example of application of photochemical cyclization reactions for the syntheses of 4H-benzo[a]pyrano[3,2-c]phenazin-4-ones (78a–g) and 4H-pyrano[2,3-a]thieno[3,2-c]phenazin-4-one (78h) involves exposing substituted 2-[3-(het)arylquinoxalin-2-yl]-4H-pyran-4-ones (77a–h) to UV radiation (365 nm) for 48 h (Scheme 14) [281].

5. Alternative Reactions for the Synthesis of 1,4-Diazatriphenylene and Related Scaffolds

Reports on the construction of 1,4-diazatriphenylene scaffolds and related structures that involve various intermolecular and intramolecular reactions, whether catalyzed by transition metals or not, are significantly less common.
A convenient method for preparing 1,4,5,8,9,12-hexaazatriphenylene (80) in 90% yield has been reported in the literature. This method involves the self-realized SNH reaction of quinoxaline (79), induced by lithiation with TMPLi, generated in situ from TMPH and n-butyllithium. Notably, neither additional additives nor halogen-containing starting materials or transition-metal catalysts were required (Scheme 15) [282].
Another example of the intermolecular cyclization leading to indolo[2,1-a]pyrazino[2,3-c]isoquinoline derivatives (82a,b) is the Buchwald–Hartwig cross-coupling between 2-phenyl-1H-indole (81) and 2,3-dibromopyrazines (62a,b) (Scheme 16) [283].
In addition to the Scholl reaction, other intramolecular processes can be used to synthesize 1,4-diazatriphenylenes, such as the Cadogan reaction and the intramolecular SNH reaction.
Specifically, the Suzuki cross-coupling reaction between 5,8-dibromoquinoxaline (83) and 2-nitrophenylboronic acid (84) yields 5,8-bis(2-nitrophenyl)quinoxaline (85). This compound is subsequently transformed into 13,14-dihydroindolo[2,3-a]pyrazino[2,3-c]carbazole (86) in a high yield under Cadogan reaction conditions (Scheme 17) [284].
A noteworthy example is the Suzuki reaction between 5-(2-bromophenyl)[1,2,5]- oxadiazolo[3,4-b]pyrazine (87) and phenylboronic acids (88a–g), which affords 5-bis(aryl)-substituted furazano[3,4-b]pyrazines (89a–g). The latter can undergo the intramolecular SNH reaction easily, provided potassium hexacyanoferrate(III) is used to oxidize the intermediate σH-adducts (90a–g). This procedure yields the desired dibenzo[f,h][1,2,5]oxadiazolo[3,4-b]-quinoxalines (91a–g) in high yields, reaching up to 96% (Scheme 18) [285].
The same synthetic method has later been applied to develop a series of new benzo[f][1,2,5]chalcogenodiazolo[3,4-b]thieno[3,2-h]quinoxalines and their benzo-fused derivatives (93a–f), as shown in Scheme 19 [286].
It is important to highlight that intramolecular SNH reactions represent a widely used method for the synthesis of polycyclic systems. This synthetic technique has also been adapted for the preparation of 1,3-diazatriphenylene derivatives and their heteroanalogs [287,288].
Palladium-catalyzed intramolecular cross-coupling reactions and direct C–H bond functionalization are effective tools for assembling 1,4-diazatriphenylenes. For instance, the compound 2,3-Di(aryl)dibenzo[f,h]quinoxaline (98) was prepared through the palladium-catalyzed intramolecular functionalization of the C(sp2)–H bond in the corresponding 2,3,5,6-tetraphenyl-substituted pyrazine (97). This pyrazine was obtained via Suzuki cross-coupling of an appropriate bromo derivative (94) (Scheme 20) [289].
In another example, polycyclic systems 102a–c were prepared in moderate yields by palladium-catalyzed intramolecular cyclizations of 9,9′-(5,8-dibromo-2,3-diphenylquinoxaline-6,7-diyl)bis(9H-carbazole) derivatives (101a–c). These substances are readily formed through the ipso-substitution of bromo atoms in 5,8-dibromo-6,7-difluoro-2,3-diphenylquinoxaline (99) with carbazole derivatives (100a–c), as shown in Scheme 21 [290].
Benzo[f]naphtho[1,2-h]quinoxaline derivatives (110a–k), which are [n]helicenes (where n = 4–6), can be obtained from either 2,3-dichloropyrazine (103) or 2,3-dichloroquinoxaline (104). This protocol involves a sequence of reactions, including Sonogashira and Suzuki cross-couplings, followed by intramolecular cyclizations proceeding in the presence of iodine monochloride and/or trifluoroacetic acid (Scheme 22) [291,292,293,294].
Polyaza[5]helicene (116) and polyaza[7]helicene (117) can be readily prepared through the Buchwald–Hartwig reaction between 1,4-dibromophenanzine (111) and 2-aminopyridine (112) [or 2-aminoquinoline (113)], followed by intramolecular oxidative N–H/C–H coupling, thus leading to 1,4-di(arylamino)phenazines (162 and 163) (Scheme 23) [295].
It is worth noting that aza[5]helicene derivatives can be synthesized from polysubstituted quinoxalines through the Bischler–Napieralski reaction. For instance, this method was used to obtain 7,10-di-tert-butyl-18,19-diphenyldinaphtho[2,1-c:1′,2′-i]pyrazino[2,3-f][1,10]phenanthroline (119) in a moderate yield from 2,3,5,6,7,8-hexasubstituted quinoxaline (118) (Scheme 24) [296].
An interesting method for preparing 2,3,7,10-tetra-substituted dibenzo[f,h]quinoxalines (123a–f) involves the reductive cyclization of substituted [1,1′-biphenyl]-2,2′-dicarbonitriles (120a–f), mediated by titanocene (121). The resulting intermediate polycyclic aromatic compounds contain a di(aza)titanium cyclopentadiene fragment (122a–f) and undergo a divergent titanocene transfer reaction to yield 1,4-diazatriphenylenes (123a–f). The authors have tried to rationalize this process as a formal [2 + 2 + 2]-reaction, leading to the formation of the pyrazine ring (Scheme 25) [297].
Another example involves the Rh(III)-catalyzed oxidative annulation of 2-arylquinoxalines (124a–j) by the action of cyclic 2-diazo-1,3-diketones (125a–e) through C−H bond activation using AgSbF6 as a cocatalyst. This process leads to the formation of 2,3-dihydrodibenzo[a,c]phenazin-4(1H)-ones (126a–u) in high yields, achieving 94% (Scheme 26) [298].
A notable method for preparing a variety of substituted dibenzo[a,c]phenazines (3a-wd) involves Brønsted acid-catalyzed “skeletal editing” of 2-arylindoles (127c-s) using 1,2-diaminoarenes (12a-cs) in the presence of tert-butyl nitrite (Scheme 27) [299]. The authors have demonstrated that this “skeletal editing” process consists of a one-pot sequence that includes five reactions: nitrosation, condensation, cyclization, diazotization, and intramolecular electrophilic substitution. However, the authors do not provide details concerning the mechanism of this process.

6. Applications of 1,4-Diazatriphenylene Derivatives and Their Heteroanalogs

Fused 1,4-diazines are well-established and promising components for photo- and/or electroactive materials used in various fields of applications [300]. Derivatives of 1,4-diazatriphenylene and its heteroanalogs (such as compounds 3ac, 21a, 25b, 26, and 27j) are promising candidates for developing semiconductor materials for organic electronics (Figure 3). These compounds can be utilized in organic field-effect transistors, light-emitting diodes (OLEDs), and solar cells [75,76,166,219].
In particular, compounds 27h, 27i, 56a,b, 58a,b, and 128a,b are considered to be promising as narrow-gap n-type semiconductors (Figure 4) [176,193,276]. Electrochemical and electrical conductivity measurements indicate that compound 128a functions effectively as an n-channel semiconductor, demonstrating the highest charge carrier mobility in this series, reaching up to 4.1 cm2·V−1·s−1 [176].
Polycyclic systems incorporating a 1,4-diazatriphenylene scaffold have often been applied as dopants in the emitter layer of thermally activated delayed fluorescence organic light-emitting diodes [18,29,35,48,49,52,57,61,66,67,78,79,80,81,83,84,85,86,93,94,101,102,103,104,105,106,113,114,115,150,156,168,179,190,214,265].
On the other hand, hetero-fused analogs of 1,4-diazatriphenylene have been utilized as non-fullerene acceptors in efficient organic solar cells and as components of polymer solar cells [183,202,206]. Table 3 provides examples of polycycles (129–134) used in the assembly of high-efficiency solar cells, along with their characteristics.
In addition, some polycyclic compounds have been identified as electrochromic materials (e.g., compounds 3ab, 22a, 22h, 22k, and 22ac) (Figure 5) [74,127] and as cathode materials in metal-ion batteries (compounds 22h and 22ag) [141,165,229,230,233,235,236,241,245,246,249,250,251,252,253,254].
Additionally, compounds of similar structures are regarded as promising as sensors for detecting nitro-explosives (compound 135) [211] and metal cations (compounds 80, 136–139) (Figure 6) [203,212,234,260]. They can also serve as excellent photocatalysts for various chemical reactions (compounds 3t, 9d, 9g, 10c, 22ak, and 22al) (Figure 7) [13,15,27,63,279].
It is important to note that metal complexes of some pyrazino[2,3-f][1,10]phenanthroline (10d) and dipyrido[3,2-a:2′,3′-c]phenazine derivatives (22a, 22d, 22j, 22u, 22x, 22ab, 22ad, and 22ae) exhibit a variety of biological activities, such as anticancer [28,124,126,134,149,152,153,161,163,169], antibacterial (compounds 22a, 22d, 22j, 22u, and 22x) [123,126,153], and antifungal properties (compound 22a) (Figure 8) [125].
Dithieno[2,3-a:3′,2′-c]phenazine derivatives (for example, compounds 140 and 141) are remarkable due to their potential as fluorescence bioimaging agents in the second near-infrared window (1000–1700 nm), which can be utilized for studying cerebrovascular functions (Figure 9) [301,302].

7. Conclusions

In this review article, we have attempted to present the latest literature data on the advances in the chemistry of 1,4-diazatriphenylene and its hetero-fused analogs, focusing on various synthetic methodologies, including condensation reactions and intramolecular cyclizations of 2,3-di(hetero)aryl-substituted pyrazine derivatives. These methods incorporate various processes such as oxidative photocyclization (the Mallory reaction), intramolecular cyclodehydrogenations proceeding through the Scholl reaction, or nucleophilic aromatic substitutions of hydrogen (the SNH reactions) in the series of 2-bis(hetero)aryl-substituted 1,4-diazine derivatives.
Additionally, the review examines the potential applications of these compounds as fluorescent and/or semiconducting materials, as well as their roles in coordination chemistry and biological properties. This review covers the literature from 2018 to March 2026, complementing the data discussed in our previous publication [4].
As follows from the review, the main method for the synthesis of 1,4-diazatriphenylenes and their condensed heteroanalogs is based on condensation of previously obtained 1,2-diamines with 1,2-diketones, and organic electronics, namely charge-transport and light-emitting materials for OLEDs, field-effect transistors, and solar cells, appears to be the main area of their potential applications. Recent publications [10,11] indicate that one of the great challenges in the chemistry of 1,4-diazines and their fused derivatives is the development of synthetic methods based on direct C–H bond functionalization.
We believe that SNH reactions, which offer innovative approaches to sustainable and green chemistry for modifying polycyclic scaffolds, have often been underestimated, resulting in their synthetic potential not being fully utilized. Additionally, [1,2,5]oxadiazolo-annulated polycyclic systems are recognized as versatile building blocks for synthesizing a range of 1,4-diazatriphenylene derivatives, thereby significantly expanding their synthetic possibilities. This versatility primarily stems from the ability of the furazan ring to be readily reduced to yield the corresponding 1,2-diamino compounds. Furthermore, these derivatives can be transformed not only into condensed imidazoles but also into a variety of 1,2,5-chalcogenadiazole derivatives [303,304]. The authors believe this review will be of help to organic chemists in developing promising materials related to polycyclic (hetero)aromatics and their metal complexes.

Author Contributions

Writing—original draft preparation, E.M.K. and Y.A.K.; writing—review and editing, E.V.V. and V.N.C.; funding acquisition, E.V.V. All authors have read and agreed to the published version of the manuscript.

Funding

The research received funding from the Ministry of Science and Higher Education of the Russian Federation within the framework of the state assignment (subject no. state. reg. 124020500039-0).

Data Availability Statement

The original research data is available upon request.

Conflicts of Interest

The authors declare no conflict of interest.

References

  1. Stępień, M.; Gońka, E.; Żyła, M.; Sprutta, N. Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications. Chem. Rev. 2017, 117, 3479–3716. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  2. Borissov, A.; Maurya, Y.K.; Moshniaha, L.; Wong, W.-S.; Żyła-Karwowska, M.; Stępień, M. Recent Advances in Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds. Chem. Rev. 2022, 122, 565–788. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  3. Cheng, H.-C.; Ma, J.-L.; Guo, P.-H.; Shi, J.-C. Cyclization Synthetic Methodologies for Triphenylene Derivatives. Chem. Asian J. 2025, 20, e00809. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  4. Verbitskiy, E.V.; Rusinov, G.L.; Charushin, V.N. Diazatriphenylenes and their thiophene analogues: Synthesis and applications. Arkivoc 2017, 2017, 356–401. [Google Scholar] [CrossRef] [Scilit]
  5. Santra, S.; Khasanov, A.F.; Mukherjee, A.; Rahman, M.; Kovalev, I.S.; Kopchuk, D.S.; Zyryanov, G.V.; Majee, A.; Chupakhin, O.N.; Charushin, V.N. Mono- and Polyazatriphenylene-Based Ligands: An Updated Library of Synthetic Strategies (2001–2018). New J. Chem. 2021, 45, 20955–20971. [Google Scholar] [CrossRef] [Scilit]
  6. Pelliccioli, V.; Arnaboldi, S.; Cauteruccio, S. Phenanthrene-like Benzodichalcogenophenes: Synthesis, Electrochemical Behavior and Applications. Molecules 2026, 31, 425. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  7. Jørgensen, K.B. Photochemical Oxidative Cyclisation of Stilbenes and Stilbenoids—The Mallory-Reaction. Molecules 2010, 15, 4334–4358. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  8. Grzybowski, M.; Skonieczny, K.; Butenschçn, H.; Gryko, D.T. Comparison of Oxidative Aromatic Coupling and the Scholl Reaction. Angew. Chem. Int. Ed. Engl. 2013, 52, 9900–9930. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  9. Jassas, R.S.; Ullah Mughal, E.; Sadiq, A.; Alsantali, R.I.; Al-Rooqi, M.M.; Naeem, N.; Moussa, Z.; Ahmed, S.A. Scholl reaction as a powerful tool for the synthesis of nanographenes: A systematic review. RSC Adv. 2021, 11, 32158–32202. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  10. Charushin, V.N.; Verbitskiy, E.V.; Chupakhin, O.N.; Vorobyeva, D.V.; Gribanov, P.S.; Osipov, S.N.; Ivanov, A.V.; Martynovskaya, S.V.; Sagitova, E.F.; Dyachenko, V.D.; et al. The chemistry of heterocycles in the 21st century. Russ. Chem. Rev. 2024, 93, RCR5125. [Google Scholar] [CrossRef] [Scilit]
  11. Verbitskiy, E.V.; Charushin, V.N. The strategy of combined application of nucleophilic aromatic substitution of hydrogen (SNH) and transition metal-catalyzed cross-coupling reactions. Mendeleev Commun. 2025, 35, 493–502. [Google Scholar] [CrossRef] [Scilit]
  12. Tajbakhsh, M.; Mazhari, F.; Nirouei, N. Preparation and characterization of sulfamic acid-functionalized Fe3O4 nanoparticles as an efficient magnetic nanocatalyst for the facile and eco-friendly synthesis of quinoxalines, benzothiazoles, and benzoxazoles. Res. Chem. Intermed. 2024, 50, 1287–1311. [Google Scholar] [CrossRef] [Scilit]
  13. He, M.; Yu, X.; Wang, Y.; Bao, M. Tunable Redox Potential Photocatalyst: Aggregates of 2,3-Dicyanopyrazino Phenanthrene Derivatives for the Visible-Light-Induced α-Allylation of Amines. J. Org. Chem. 2021, 86, 14720–14731. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  14. Alameddine, B.; Baig, N.; Shetty, S.; Al-Mousawi, S. Conjugated copolymers bearing 2,7-di(thiophen-2-yl)phenanthrene-9,10-dione units and alteration of their emission via functionalization of the ortho-dicarbonyl groups into quinoxaline and phenazine derivatives. Polymer 2019, 178, 121589. [Google Scholar] [CrossRef] [Scilit]
  15. He, M.; Yang, S.; Yu, X.; Bao, M. 7,10-Dibromo-2,3-dicyanopyrazinophenanthrene Aggregates as a Photosensitizer for Nickel-Catalyzed Aryl Esterification. Synlett 2022, 33, 1189–1193. [Google Scholar] [CrossRef] [Scilit]
  16. Kalhor, M.; Shayestefar, M.; Khalaj, M.; Janghorban, F. Ca(IO3)2 nanoparticles: Fabrication and application as an eco-friendly and recyclable catalyst for the green synthesis of quinoxalines, pyridopyrazines, and 2,3-dicyano pyrazines. Res. Chem. Intermed. 2023, 49, 885–900. [Google Scholar] [CrossRef] [Scilit]
  17. Spychalska, Z.; Adamek, J.; Buchowicz, W.; Durka, K.; Luliński, S. Structural Expansion of Dibenzo[b,d]thiophene Sulfone through Functionalization at Bay Positions. Org. Lett. 2025, 27, 9136–9140. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  18. Furue, R.; Matsuo, K.; Ashikari, Y.; Ooka, H.; Amanokura, N.; Yasuda, T. Highly Efficient Red–Orange Delayed Fluorescence Emitters Based on Strong π-Accepting Dibenzophenazine and Dibenzoquinoxaline Cores: Toward a Rational Pure-Red OLED Design. Adv. Opt. Mater. 2018, 6, 1701147. [Google Scholar] [CrossRef] [Scilit]
  19. Ge, C.; Liu, J.; Ye, X.; Han, Q.; Zhang, L.; Cui, S.; Guo, Q.; Liu, G.; Liu, Y.; Tao, X. Visualization of Single-Crystal-to-Single-Crystal Phase Transition of Luminescent Molecular Polymorph. J. Phys. Chem. C 2018, 122, 15744–15752. [Google Scholar] [CrossRef] [Scilit]
  20. Zhiyang, L.; Qifeng, X.; Shuang, S.; Xueyan, R. Novel Compound and Organic Electroluminescent Device Using the Same. Patent CN109593082A, 30 September 2017. [Google Scholar]
  21. Zhiyang, L.; Qifeng, X.; Shuang, S.; Xueyan, R. Novel Compound and Organic Electroluminescent Device Using the Same. Patent CN109593086A, 30 September 2017. [Google Scholar]
  22. Singh, P.S.; Chacko, S.; Kamble, R.M. Dicyanopyrazino phenanthrene based charge transfer derivatives: Role of amine donor in tuning of photophysical, aggregation-induced emission, electrochemical and theoretical properties. J. Mol. Struct. 2023, 1271, 134052. [Google Scholar] [CrossRef] [Scilit]
  23. Lin, Z.; Wang, H.; Xiang, H.; Wu, J.; Cui, J.; Chen, J.; Chen, X. Orthogonal Photo- and Thermo-Responsive Fluorescent Polymeric Hydrogels for Multi-Level Information Encryption and Anti-Counterfeiting. Adv. Opt. Mater. 2024, 12, 2401604. [Google Scholar] [CrossRef] [Scilit]
  24. Kitagawa, Y.; Kumagai, M.; Nakanishi, T.; Fushimi, K.; Hasegawa, Y. First Aggregation-Induced Emission of a Tb(III) Luminophore Based on Modu-lation of Ligand–Ligand Charge Transfer Bands. Dalton Trans. 2020, 49, 2431–2436. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  25. Kitagawa, Y.; Kumagai, M.; Fushimi, K.; Hasegawa, Y. Aggregation-induced emission of a Eu(III) complex via ligand-to-metal charge transfer. Chem. Phys. Lett. 2020, 749, 137437. [Google Scholar] [CrossRef] [Scilit]
  26. Zaifeng, X.; Tianyu, W.; Zhe, S.; Songyuan, L. Phenanthroline Derivative and Organic Electroluminescent Device Comprising Same. Patent CN117024427A, 14 July 2023. [Google Scholar]
  27. Sosoe, J.; Cruché, C.; Morin, É.; Collins, S.K. Evaluating Heteroleptic Copper(I)-Based Complexes Bearing π-Extended Diimines in Different Photocatalytic Processes. Can. J. Chem. 2020, 98, 461–465. [Google Scholar] [CrossRef] [Scilit]
  28. Rocha, J.S.; Pereira, G.B.S.; Oliveira, G.P.; Lima, M.A.; Araujo-Neto, J.H.; Pinto, L.S.; Forim, M.R.; Zanetti, R.D.; Netto, A.V.G.; Castellano, E.E.; et al. Synthesis and characterization of silver(I) complexes bearing phenanthroline derivatives as ligands: Cytotoxicity and DNA interaction evaluation. Inorg. Chem. Commun. 2021, 131, 108757. [Google Scholar] [CrossRef] [Scilit]
  29. Cai, Z.; Wu, X.; Liu, H.; Guo, J.; Yang, D.; Ma, D.; Zhao, Z.; Tang, B.Z. Realizing Record-High Electroluminescence Efficiency of 31.5 % for Red Thermally Activated Delayed Fluorescence Molecules. Angew. Chem. Int. Ed. Engl. 2021, 60, 23635–23640. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  30. Wang, H.; Zhao, B.; Qu, C.; Duan, C.; Li, Z.; Ma, P.; Chang, P.; Han, C.; Xu, H. 2,3-Dicyanopyrazino Phenanthroline Enhanced Charge Transfer for Effi-cient Near-Infrared Thermally Activated Delayed Fluorescent Diodes. Chem. Eng. J. 2022, 436, 135080. [Google Scholar] [CrossRef] [Scilit]
  31. Zhang, Y.; Wu, J.; Song, J.; Chen, Z.; He, J.; Wang, X.; Liu, H.; Chen, S.; Qu, J.; Wong, W.-Y. Achieving High-Performance Solution-Processed Deep-Red/Near-Infrared Organic Light-Emitting Diodes with a Phenanthroline-Based and Wedge-Shaped Fluorophore. Adv. Electron. Mater. 2019, 5, 1800677. [Google Scholar] [CrossRef] [Scilit]
  32. Chang, X.; Lu, K.; Zeng, S.; Liu, D.; Huang, J.; Ma, B.; Wang, L.; Gan, X.; Yu, J.; Wang, Y.; et al. High-Efficiency Long-Wavelength NIR Iridium Complexes Constructed by Extending Rigid Coordination and Optimizing Peripheral Donor Position to Break Cocoon into Butterfly. Chem. Eng. J. 2023, 475, 146031. [Google Scholar] [CrossRef] [Scilit]
  33. Hogan, D.T.; Gelfand, B.S.; Spasyuk, D.M.; Sutherland, T.C. Subtle Substitution Controls the Rainbow Chromatic Behaviour of Multi-Stimuli Responsive Core-Expanded Pyrenes. Mater. Chem. Front. 2020, 4, 268–276. [Google Scholar] [CrossRef] [Scilit]
  34. Ueberricke, L.; Ciubotaru, I.; Ghalami, F.; Mildner, F.; Rominger, F.; Elstner, M.; Mastalerz, M. Di- and Tetracyano-Substituted Pyrene-Fused Pyrazaacenes: Aggregation in the Solid State. Chem. Eur. J. 2020, 26, 11634–11642. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  35. Yang, T.; Cheng, Z.; Li, Z.; Liang, J.; Xu, Y.; Li, C.; Wang, Y. Improving the Efficiency of Red Thermally Activated Delayed Fluorescence Organic Light-Emitting Diode by Rational Isomer Engineering. Adv. Funct. Mater. 2020, 30, 2002681. [Google Scholar] [CrossRef] [Scilit]
  36. Merz, J.; Dietz, M.; Vonhausen, Y.; Wöber, F.; Friedrich, A.; Sieh, D.; Krummenacher, I.; Braunschweig, H.; Moos, M.; Holzapfel, M.; et al. Synthesis, Photophysical and Electronic Properties of New Red-to-NIR Emitting Donor–Acceptor Pyrene Derivatives. Chem. Eur. J. 2020, 26, 438–453. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  37. Harsha, K.B.; Rangappa, S.; Preetham, H.D.; Swaroop, T.R.; Gilandoust, M.; Rakesh, K.S.; Rangappa, K.S. An Easy and Efficient Method for the Synthesis of Quinoxalines Using Recyclable and Heterogeneous Nanomagnetic-Supported Acid Catalyst under Solvent-Free Condition. ChemistrySelect 2018, 3, 5228–5232. [Google Scholar] [CrossRef] [Scilit]
  38. Sajjadifar, S.; Amini, I.; Mansouri, G.; Alimohammadi, S. Fe3O4@APTES@isatin-SO3H as Heterogeneous and Efficient Catalyst for the Synthesis of Quinoxaline Derivatives. Eurasian Chem. Commun. 2020, 2, 626–633. [Google Scholar] [CrossRef] [Scilit]
  39. Patil, M.U.; Shinde, S.K.; Patil, S.P.; Patil, S.S. [BBSA-DBN][HSO4]: A novel –SO3H functionalized Bronsted acidic ionic liquid for easy access of quinoxalines. Res. Chem. Intermed. 2020, 46, 4923–4938. [Google Scholar] [CrossRef] [Scilit]
  40. Arde, S.M.; Patil, A.D.; Mane, A.H.; Salokhe, P.R.; Salunkhe, R.S. Synthesis of Quinoxaline, Benzimidazole and Pyrazole Derivatives Under the Catalytic Influence of Biosurfactant-Stabilized Iron Nanoparticles in Water. Res. Chem. Intermed. 2020, 46, 5069–5086. [Google Scholar] [CrossRef] [Scilit]
  41. Sajjadifar, S.; Mansouri, G.; Amini, I.; Yari, M. Silica Supported 1-(2-(Sulfooxy)ethyl)pyridin-1-ium Chloride (SiO2/[SEP]Cl) as an Efficient and Solid Acid Catalyst for the Synthesis of Quinoxaline Derivatives. J. Med. Chem. Sci. 2021, 4, 8–16. [Google Scholar] [CrossRef]
  42. Tamuli, K.J.; Nath, S.; Bordoloi, M. In Water Organic Synthesis: Introducing Itaconic Acid as a Recyclable Acidic Promoter for Efficient and Scalable Synthesis of Quinoxaline Derivatives at Room Temperature. J. Heterocycl. Chem. 2021, 58, 983–1002. [Google Scholar] [CrossRef] [Scilit]
  43. Kaur, G.; Singh, A.; Kaur, N.; Banerjee, B. General Method for the Synthesis of Structurally Diverse Quinoxalines and Pyrido-pyrazine Derivatives Using Camphor Sulfonic Acid as an Efficient Organo-catalyst at Room Temperature. Synth. Commun. 2021, 51, 1121–1131. [Google Scholar] [CrossRef] [Scilit]
  44. Amaya-García, F.; Caldera, M.; Koren, A.; Kubicek, S.; Menche, J.; Unterlass, M.M. Green Hydrothermal Synthesis of Fluorescent 2,3-Diarylquinoxalines and Large-Scale Computational Comparison to Existing Alternatives. ChemSusChem 2021, 14, 1853–1863. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  45. Yaghubzadeh, M.; Alavinia, S.; Ghorbani-Vaghei, R.; Koosha, S. The Preparation, Characterization and Catalytic Activity of Porous Tragacanth Gum -g-Poly (p-Styrene Sulfonamide-co-Acrylamide). J. Mol. Struct. 2023, 1293, 136265. [Google Scholar] [CrossRef] [Scilit]
  46. Hu, Y.; Hong, Y.; Zheng, Y.; Huang, Y.; Chen, J.; Wu, X. Synthesis of Antimicrobial Active 9,10-Phenanthrenequinones by Carbene Organocatalytic Tandem Reactions. Org. Chem. Front. 2025, 12, 1778–1785. [Google Scholar] [CrossRef] [Scilit]
  47. Saaei, M.; Mazloumi, M.; Seyedi, N.; Shirini, F. Introduction of [DABCO](SO3H)2CoCl4 as a New Catalyst for the Synthesis of Quinoxaline, 2,4,5-Triarylimidazole, N,N′−Diarylformamidine, and Benzazole Derivatives. J. Iran. Chem. Soc. 2025, 22, 1431–1452. [Google Scholar] [CrossRef] [Scilit]
  48. Zhou, C.; Chen, W.-C.; Liu, H.; Cao, X.; Li, N.; Zhang, Y.; Lee, C.-S.; Yang, C. Isomerization Enhanced Quantum Yield of Dibenzo[a,c]phenazine-Based Thermally Activated Delayed Fluorescence Emitters for Highly Efficient Orange OLEDs. J. Mater. Chem. C 2020, 8, 9639–9645. [Google Scholar] [CrossRef] [Scilit]
  49. Maeng, J.H.; Braveenth, R.; Jung, Y.H.; Hwang, S.J.; Lee, H.; Min, H.L.; Kim, J.Y.; Han, C.W.; Kwon, J.H. Efficiency Enhancement in Orange Red Thermally Activated Delayed Fluorescence OLEDs by Using a Rigid Di-indolocarbazole Donor Moiety. Dye. Pigment. 2021, 194, 109580. [Google Scholar] [CrossRef] [Scilit]
  50. Peña, B.; Saha, S.; Barhoumi, R.; Burghardt, R.C.; Dunbar, K.R. Ruthenium(II)-Polypyridyl Compounds with π-Extended Nitrogen Donor Ligands Induce Apoptosis in Human Lung Adenocarcinoma (A549) Cells by Triggering Caspase-3/7 Pathway. Inorg. Chem. 2018, 57, 12777–12786. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  51. Lee, S.H.; Matula, A.J.; Hu, G.; Troiano, J.L.; Karpovich, C.J.; Crabtree, R.H.; Batista, V.S.; Brudvig, G.W. Strongly Coupled Phenazine–Porphyrin Dyads: Light-Harvesting Molecular Assemblies with Broad Absorption Coverage. ACS Appl. Mater. Interfaces 2019, 11, 8000–8008. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  52. Zhou, C.; Xiao, S.; Wang, M.; Jiang, W.; Liu, H.; Zhang, S.; Yang, B. Modulation of Excited State Property Based on Benzo[a,c]phenazine Acceptor: Three Typical Excited States and Electroluminescence Performance. Front. Chem. 2019, 7, 141. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  53. Müller, J.; Buck, J.; Hirsch, A. Carpet Beater Molecules: Synthesis and Characterization of Functional Hexa-peri-benzocoronene—Alkyne Coupling Products. Eur. J. Org. Chem. 2023, 26, e202201310. [Google Scholar] [CrossRef] [Scilit]
  54. Isoda, K.; Orita, Y. Stimuli-responsive Behaviors for Room-temperature Fluorescent Liquid Materials based on N-Heteroacenes and their Mixtures in Response to HCl Vapor and their Facile Synthesis. Anal. Sci. 2021, 37, 469–473. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  55. Amaya-García, F.; Unterlass, M.M. Synthesis of 2,3-Diarylquinoxaline Carboxylic Acids in High-Temperature Water. Synthesis 2022, 54, 3367–3382. [Google Scholar] [CrossRef] [Scilit]
  56. Li, Y.; Han, S.; Zhao, H.; Weng, J.; Liu, Y.; Li, X.; Wang, G. Efficient Energy Phosphorescence Transfer and Reversible Phosphorescence in Aromatic Heterocyclic Doped Systems for Advanced Information Storage. Spectrochim. Acta—A Mol. Biomol. Spectrosc. 2025, 336, 126053. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  57. Si, C.; Hu, Y.-N.; Sun, D.; Wang, K.; Zhang, X.-H.; Zysman-Colman, E. The Influence of Nitrogen Doping of the Acceptor in Orange-Red Thermally Activated Delayed Fluorescence Emitters and OLEDs. J. Mater. Chem. C 2023, 11, 12174–12184. [Google Scholar] [CrossRef] [Scilit]
  58. Lyu, L.; Su, R.; Al-Qaradawi, S.Y.; Al-Saad, K.A.; El-Shafei, A. Three-Component One-Pot Reaction for Molecular Engineering of Novel Cost-Effective Highly Rigid Quinoxaline-Based Photosensitizers for Highly Efficient DSSCs Application: Remarkable Photovoltage. Dye. Pigment. 2019, 171, 107683. [Google Scholar] [CrossRef] [Scilit]
  59. Liu, M.; Zheng, Z.; Jiang, X.; Guo, F.; Mola, G.T.; Gao, S.; Zhao, L.; Zhang, Y. Fluorinated Phenanthrenequinoxaline-Based D-A Type Copolymers for Non-Fullerene Polymer Solar Cells. Polymer 2022, 250, 124867. [Google Scholar] [CrossRef] [Scilit]
  60. Fu, W.; Chen, H.; Han, Y.; Wang, W.; Zhang, R.; Liu, J. Electropolymerization of D–A–D Type Monomers Consisting of Triphenylamine and Substituted Quinoxaline Moieties for Electrochromic Devices. New J. Chem. 2021, 45, 19082–19087. [Google Scholar] [CrossRef] [Scilit]
  61. Si, C.; Sun, D.; Matulaitis, T.; Cordes, D.B.; Slawin, A.M.Z.; Zysman-Colman, E. Rational Molecular Design of Efficient Yellow-Red Dendrimer TADF for Solution-Processed OLEDs: A Combined Effect of Substitution Position and Strength of the Donors. Sci. China Chem. 2024, 67, 1613–1623. [Google Scholar] [CrossRef] [Scilit]
  62. You, C.; Liu, D.; Yu, J.; Tan, H.; Zhu, M.; Zhang, B.; Liu, Y.; Wang, Y.; Zhu, W. Boosting Efficiency of Near-Infrared Emitting Iridium(III) Phosphors by Administrating Their π–π Conjugation Effect of Core–Shell Structure in Solution-Processed OLEDs. Adv. Opt. Mater. 2020, 8, 2000154. [Google Scholar] [CrossRef] [Scilit]
  63. Deol, H.; Singh, G.; Kumar, M.; Bhalla, V. Phenazine-Based Donor Acceptor Systems as Organic Photocatalysts for “Metal-free” C–N/C–C Cross-Coupling. J. Org. Chem. 2020, 85, 11080–11093. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  64. Fu, N.; Zou, X.; Zhao, B.; Wang, L.; Chong, B.; Tian, M. Thermal Activation Delayed Fluorescence Semiconductor Material and Preparation Method and Application Thereof. Patent CN114621151A, 25 March 2022. [Google Scholar]
  65. Ghosh, P.; Ratha, R.; Purohit, C.S. Functionalization of a [2]Catenane with Donor-Acceptor Chromophores Using a Metal Template and Click Reactions. Chem. Asian J. 2024, 19, e202400668. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  66. Wang, Y.-Y.; Zhang, Y.-L.; Tong, K.; Ding, L.; Fan, J.; Liao, L.-S. Highly Efficient Red Thermally Activated Delayed Fluorescence Materials Based on a Cyano-Containing Planar Acceptor. J. Mater. Chem. C 2019, 7, 15301–15307. [Google Scholar] [CrossRef] [Scilit]
  67. Liu, B.; Chen, S.-W.; Chen, W.-C.; Xing, L.; Tan, J.-H.; Wu, W.-L.; Liu, X.-L.; Chen, J.-X.; Zhang, H.-L.; Huo, Y. Efficient Thermally Activated Delayed Fluorophores Featuring Multi-Donor Arms and a π-Extended Acceptor Core. J. Mater. Chem. C 2024, 12, 6406–6414. [Google Scholar] [CrossRef] [Scilit]
  68. Peng, H.; Xiao, J.; Wu, Z.; Zhang, L.; Geng, Y.; Xin, W.; Li, J.; Yan, Z.; Zhang, K.; Zhu, Z. N-Heterocycles Extended π-Conjugation Enables Ultrahigh Capacity, Long-Lived, and Fast-Charging Organic Cathodes for Aqueous Zinc Batteries. CCS Chem. 2023, 5, 1789–1801. [Google Scholar] [CrossRef] [Scilit]
  69. Peng, H.; Han, Y.; Zhang, L.; Geng, Y.; Yu, Z.; Xu, C.; Yuan, Y.; Zhou, Z.; Liang, X.; Zhu, J.; et al. Boosting Lithium Storage Performance of Small-Molecule Organic Cathodes through Synergistic Molecular Engineering and Nanostructure Design. Angew. Chem. Int. Ed. 2025, 64, e202502088. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  70. Morawski, O.W.; Gawryś, P.; Sobolewski, A.L. Harnessing Proton-Coupled Electron Transfer for Hydrogenation of Aza-Arenes: Photochemistry of Quinoxaline Derivatives in Methanol. J. Phys. Chem. A 2023, 127, 8871–8881. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  71. Naz, F.; Si, C.; Kellici, S.; Sajjad, M.T.; Zysman-Colman, E. Red and Near-Infrared Thermally Activated Delayed Fluorescence Emitters Based on a Dibenzo[f,h]pyrido[2,3-b]quinoxaline Acceptor. Chem. Asian J. 2025, 20, e202500136. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  72. Liang, Y.; He, L.; Huang, W.; Qui, W.; Li, S.; Zheng, K.; Wang, D.; Gong, X.; Li, Z. 6,7-Disubstituted 2-(Ethylthio)-pteridine-4-amine Derivative and Preparation Method and Application Thereof. Patent CN113831347A, 22 October 2021. [Google Scholar]
  73. Fang, J.; An, D.; Chen, W.; Liu, S.; Lu, X.; Zhou, G. Manipulating Intramolecular Charge Transfer and Supramolecular Interaction in D–A–D Conjugated Systems by Regioisomerization. J. Org. Chem. 2024, 89, 4523–4529. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  74. Fu, W.; Chen, H.; Yi, X.; Zhang, R.; Liu, J. Electrochemical Polymerization of D-A-D Type Monomers Consisting of Triphenylamine and Benzo [1,2-b:4,5-b′]dipyrazine Units for Multicolor Electrochromism. Eur. Polym. J. 2022, 173, 111274. [Google Scholar] [CrossRef] [Scilit]
  75. Yuan, Y.; Lo, K.-C.; Szeto, L.; Chan, W.-K. Synthesis of Pyrazinopyrazine-Fused Azaacenes through Direct Condensation Reactions between Quinoxalinediamine and Diketones. J. Org. Chem. 2020, 85, 6372–6379. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  76. Pan, H.; Song, T.; Yin, X.; Jin, P.; Xiao, J. Synthesis, Crystal Analysis, and Optoelectronic Properties of Diazole-Functionalized Acenes and Azaacenes. Chem. Eur. J. 2018, 24, 6572–6579. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  77. Lai, H.; Chen, H.; Zhu, Y.; Wang, H.; Li, Y.; He, F. Aggregation of Small Molecule and Polymer Acceptors with 2D-Fused Backbones in Organic Solar Cells. Macromolecules 2022, 55, 3353–3360. [Google Scholar] [CrossRef] [Scilit]
  78. Xie, F.-M.; Wu, P.; Zou, S.-J.; Li, Y.-Q.; Cheng, T.; Xie, M.; Tang, J.-X.; Zhao, X. Efficient Orange–Red Delayed Fluorescence Organic Light-Emitting Diodes with External Quantum Efficiency over 26%. Adv. Electron. Mater. 2020, 6, 1900843. [Google Scholar] [CrossRef] [Scilit]
  79. Wang, H.; Wang, K.; Chen, J.-X.; Zhang, X.; Zhou, L.; Fan, X.-C.; Cheng, Y.-C.; Hao, X.-Y.; Yu, J.; Zhang, X.-H. Enabling Record-high Deep-Red/Near-Infrared Electroluminescence Through Subtly Managing Intermolecular Interactions of a Thermally Activated Delayed Fluorescence Emitter. Adv. Funct. Mater. 2023, 33, 2304398. [Google Scholar] [CrossRef] [Scilit]
  80. Wang, H.; Lin, S.; Chen, J.-X.; Hao, X.-Y.; Fan, X.-C.; Shi, Y.-Z.; Yu, J.; Chen, X.-K.; Wang, K.; Zhang, X.-H. Stepwise Planarizing Geometries of D–A Type Red Thermally Activated Delayed Fluorescence Molecules in Condensed States Toward High-Efficiency Red/NIR OLEDs. Adv. Funct. Mater. 2025, 35, 2420489. [Google Scholar] [CrossRef] [Scilit]
  81. Cui, L.-S.; Zhu, X.; Zhang, Y.; Chen, H. Phenanthropyrazine Derivative and Preparation Method Thereof, and Electronic Device. Patent CN111253407A, 27 March 2020. [Google Scholar]
  82. Chen, J.-X.; Tao, W.-W.; Xiao, Y.-F.; Tian, S.; Chen, W.-C.; Wang, K.; Yu, J.; Geng, F.-X.; Zhang, X.-H.; Lee, C.-S. Isomeric Thermally Activated Delayed Fluorescence Emitters Based on Indolo [2,3-b]acridine Electron-Donor: A Compromising Optimization for Efficient Orange–Red Organic Light-Emitting Diodes. J. Mater. Chem. C 2019, 7, 2898–2904. [Google Scholar] [CrossRef] [Scilit]
  83. Chen, J.-X.; Tao, W.-W.; Chen, W.-C.; Xiao, Y.-F.; Wang, K.; Cao, C.; Yu, J.; Li, S.; Geng, F.-X.; Adachi, C.; et al. Red/Near-Infrared Thermally Activated Delayed Fluorescence OLEDs with Near 100 % Internal Quantum Efficiency. Angew. Chem. Int. Ed. Engl. 2019, 58, 14660–14665. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  84. Zhou, L.; Wang, H.; Shi, Y.-Z.; Fan, X.-C.; Chen, J.-X.; Wang, K.; Yu, J.; Zhang, X.-H. Controlling the Conjugation Extension Inside Acceptors for Enhancing Reverse Intersystem Crossing of Red Thermally Activated Delayed Fluorescence Emitters. Chem. Eng. J. 2022, 440, 135775. [Google Scholar] [CrossRef] [Scilit]
  85. Feng, Q. Green Light Compound Based on Dibenzophenazine, Preparation Method and Device Thereof. Patent CN113214286A, 13 May 2021. [Google Scholar]
  86. Yao, M.-M.; Yang, B.; Zhang, S.; Zhang, Y.; Zhang, Y. Pure Organic Fluorescent Micromolecule with High Exciton Utilization Rate and Application. Patent CN113896719A, 18 November 2021. [Google Scholar]
  87. Sk, B.; Sarkar, M.; Singh, K.; Senguptab, A.; Patra, A. UV to NIR Multistate Electrochromism and Electrofluorochromism in Dibenzophenazine-Arylamine. Chem. Commun. 2021, 57, 13590–13593. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  88. Sk, B.; Sharma, S.; James, A.; Kundu, S.; Patra, A. N-Rich Electron Acceptors: Triplet Harvesting in Multichromophoric Pyridoquinoxaline and Pyridopyrazine-Based Organic Emitters. J. Mater. Chem. C 2020, 8, 12943–12950. [Google Scholar] [CrossRef] [Scilit]
  89. Sk, B.; Khodia, S.; Patra, A. T and V-Shaped Donor–Acceptor–Donor Molecules Involving Pyridoquinoxaline: Large Stokes Shift, Environment-Sensitive Tunable Emission and Temperature-Induced Fluorochromism. Chem. Commun. 2018, 54, 1786–1789. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  90. Raman, R.; Natarajan, B.; Sundararajan, M.L. Novel Quinoxaline Derivatives: Synthesis, Thermal, Photo Physical Studies and Biological Activity. Rasayan J. Chem. 2022, 15, 162–170. [Google Scholar] [CrossRef] [Scilit]
  91. Zheng, J.; Zhou, X. Quinoxaline Compound, Polymer, Organic Electronic Device and Display Panel. Patent CN113248451A, 27 April 2020. [Google Scholar]
  92. Pal, S.; Fatma, K.; Ravichandiran, V.; Dash, J. Triazolyl Dibenzo[a,c]phenazines Stabilize Telomeric G-quadruplex and Inhibit Telomerase. Asian J. Org. Chem. 2021, 10, 2921–2926. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  93. Sun, K.; Cai, Z.; Jiang, J.; Tian, W.; Guo, W.; Shao, J.; Jiang, W.; Sun, Y. Multi-Substituted Dibenzo[a,c]phenazine Derivatives as Solution-Processable Thermally Activated Delayed Fluorescence Materials for Orange–Red Organic Light-Emitting Diodes. Dye. Pigment. 2020, 173, 107957. [Google Scholar] [CrossRef] [Scilit]
  94. Sun, K.; Teng, Y.; Zhou, L.; Xu, X.; Cai, Z.-S. Thermal Activation Delayed Fluorescence Material Based on Dibenzophenazine Derivative as Well as Preparation Method and Application of Thermal Activation Delayed Fluorescence Material. Patent CN111574514A, 29 May 2020. [Google Scholar]
  95. Kanekar, D.N.; Badani, P.M.; Kamble, R.M. Study of Modulating Opto-Electrochemical Properties in Suzuki Coupled Phenazine Derivatives for Organic Electronics. Chem. Pap. 2021, 75, 5945–5961. [Google Scholar] [CrossRef] [Scilit]
  96. Jamel, N.S.M.; Skhirtladze, L.; Hussein, A.A.; Ma, Y.; Woon, K.L.; Abdulwahab, M.K.; Grazulevicius, J.V.; Ariffin, A. Microwave-Assisted Buchwald–Hartwig Double Amination: A Rapid and Promising Approach for the Synthesis of TADF Compounds. ACS Omega 2024, 9, 50446–50457. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  97. Liang, J.; Li, C.; Cui, Y.; Li, Z.; Wang, J.; Wang, Y. Rational Design of Efficient Orange-Red to Red Thermally Activated Delayed Fluorescence Emitters for OLEDs with External Quantum Efficiency of up to 26.0% and Reduced Efficiency Roll-off. J. Mater. Chem. C 2020, 8, 1614–1622. [Google Scholar] [CrossRef] [Scilit]
  98. Kanekar, D.N.; Chacko, S.; Kamble, R.M. Synthesis and Investigation of the Photophysical, Electrochemical and Theoretical Properties of Phenazine–Amine Based Cyan Blue-Red Fluorescent Materials for Organic Electronics. New J. Chem. 2020, 44, 3278–3293. [Google Scholar] [CrossRef] [Scilit]
  99. Tang, J.-X.; Xie, F.; Li, Y.; Zhou, J.-X.; Zeng, X.-Y. Chiral Thermally Activated Delayed Fluorescence Material and Preparation Method Thereof. Patent WO2022052135A1, 14 September 2020. [Google Scholar]
  100. Liu, H.; Zhang, K.; Zou, H.; Mu, Q.; Song, Y.; Lin, L.; Xu, Y.; Wang, C.-K.; Fan, J. Controllable Construction of Red Thermally Activated Delayed Fluorescence Molecules Based on a Spiro-Acridine Donor. Phys. Chem. Chem. Phys. 2023, 25, 1032–1044. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  101. Kothavale, S.; Chung, W.J.; Lee, J.Y. Rational Molecular Design of Highly Efficient Yellow-Red Thermally Activated Delayed Fluorescent Emitters: A Combined Effect of Auxiliary Fluorine and Rigidified Acceptor Unit. ACS Appl. Mater. Interfaces 2020, 12, 18730–18738. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  102. Huang, F.-X.; Li, H.-Z.; Xie, F.-M.; Zeng, X.-Y.; Li, Y.-Q.; Hu, Y.-Y.; Tang, J.-X.; Zhao, X. Efficient Orange-Red Thermally Activated Delayed Fluorescence Material Containing a Cyano Group. Dye. Pigment. 2021, 195, 109731. [Google Scholar] [CrossRef] [Scilit]
  103. Wang, S.; Miao, Y.; Yan, X.; Ye, K.; Wang, Y. A Dibenzo[a,c]phenazine-11,12-dicarbonitrile (DBPzDCN) Acceptor Based Thermally Activated Delayed Fluorescent Compound for Efficient Near-Infrared Electroluminescent Devices. J. Mater. Chem. C 2018, 6, 6698–6704. [Google Scholar] [CrossRef] [Scilit]
  104. Zhang, Y.-L.; Ran, Q.; Wang, Q.; Liu, Y.; Hänisch, C.; Reineke, S.; Fan, J.; Liao, L.-S. High-Efficiency Red Organic Light-Emitting Diodes with External Quantum Efficiency Close to 30% Based on a Novel Thermally Activated Delayed Fluorescence Emitter. Adv. Mater. 2019, 31, 1902368. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  105. Xie, F.-M.; Zeng, X.-Y.; Zhou, J.-X.; An, Z.-D.; Wang, W.; Li, Y.-Q.; Zhang, X.-H.; Tang, J.-X. Intramolecular H-bond Design for Efficient Orange–Red Thermally Activated Delayed Fluorescence Based on a Rigid Dibenzo[f,h]pyrido[2,3-b]quinoxaline Acceptor. J. Mater. Chem. C 2020, 8, 15728–15734. [Google Scholar] [CrossRef] [Scilit]
  106. Tang, J.-X.; Zhou, J.-X.; Tang, Y.; Li, Y.; Zeng, X.-Y. Orange-Red Light Thermally Activated Delayed Fluorescent Material and Synthesis Method Therefor. Patent WO2024026688A1, 8 February 2022. [Google Scholar]
  107. Putta, A.; Gairhe, S.; Feng, Y.; Sun, H. Stereo-Electronic Effect of the Perfluoropropyl Group on the Solid-State Molecular Packing of Isomeric Dibenzo[a,c]phenazine. CrystEngComm 2022, 24, 1891–1899. [Google Scholar] [CrossRef] [Scilit]
  108. Sun, H. Fluorinated-Polymer Coated Electrodes. Patent US20180198128A1, 12 January 2018. [Google Scholar]
  109. Primrose, W.L.; Mayder, D.M.; Hojo, R.; Hudson, Z.M. Dibenzodipyridophenazines with Dendritic Electron Donors Exhibiting Deep-Red Emission and Thermally Activated Delayed Fluorescence. J. Org. Chem. 2023, 88, 4224–4233. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  110. Si, C.; Wang, T.; Xu, Y.; Lin, D.; Sun, D.; Zysman-Colman, E. A Temperature Sensor with a Wide Spectral Range Based on a Dual-Emissive TADF Dendrimer System. Nat. Commun. 2024, 15, 7439. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  111. Hu, M.-H.; Lin, J.-H. New Dibenzoquinoxalines Inhibit Triple-Negative Breast Cancer Growth by Dual Targeting of Topoisomerase 1 and the c-MYC G-Quadruplex. J. Med. Chem. 2021, 64, 6720–6729. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  112. Zheng, C.-J.; Ge, C.; Yin, P. Organic Thermally-Induced Delayed Fluorescence Material Based on Pyrazine Receptor as Well as Preparation Method and Application of Organic Thermally-Induced Delayed Fluorescence Material. Patent CN112961148A, 20 February 2021. [Google Scholar]
  113. Chen, J.-X.; Xiao, Y.-F.; Wang, K.; Sun, D.; Fan, X.-C.; Zhang, X.; Zhang, M.; Shi, Y.-Z.; Yu, J.; Geng, F.-X.; et al. Managing Locally Excited and Charge-Transfer Triplet States to Facilitate Up-Conversion in Red TADF Emitters That Are Available for Both Vacuum- and Solution-Processes. Angew. Chem. Int. Ed. Engl. 2021, 60, 2478–2484. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  114. Balijapalli, U.; Lee, Y.-T.; Karunathilaka, B.S.B.; Tumen-Ulzii, G.; Auffray, M.; Tsuchiya, Y.; Nakanotani, H.; Adachi, C. Tetrabenzo[a,c]phenazine Backbone for Highly Efficient Orange–Red Thermally Activated Delayed Fluorescence with Completely Horizontal Molecular Orientation. Angew. Chem. Int. Ed. Engl. 2021, 60, 19364–19373. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  115. Li, Y.; Liu, Y.; Gao, Y.; Zhang, K.; Sun, Y.-Q.; Ding, L.; Fung, M.-K.; Fan, J. Over 30% External Quantum Efficiency for Doping-Free D-A-Type Thermally Activated Delayed Fluorescence Organic Light-Emitting Diodes. Chem. Eng. J. 2024, 488, 151155. [Google Scholar] [CrossRef] [Scilit]
  116. Patra, A.; Behera, P.K.; Shah, A.; Singh, D.P.; Raghunathan, V.A.; Sudhakar, A.A.; Kumar, S. Exploring the Ambipolar Charge Carrier Mobility, Mesomorphic, and Gel Properties in Nitrile Extended Quinoxaline and Phenanthro[a]phenazine Discotic Liquid Crystals. ACS Appl. Electron. Mater. 2024, 6, 4891–4902. [Google Scholar] [CrossRef] [Scilit]
  117. Zellman, C.O.; Vu, D.; Williams, V.E. Adjacent Functional Group Effects on the Assembly of Columnar Liquid Crystals. Can. J. Chem. 2020, 98, 379–385. [Google Scholar] [CrossRef] [Scilit]
  118. Voisin, E.; Williams, V.E. The Impact of Molecular Symmetry and Shape on the Stability of Discotic Liquid Crystals. Can. J. Chem. 2018, 96, 132–138. [Google Scholar] [CrossRef] [Scilit]
  119. Yuan, W.; Ren, X.-K.; Li, M.; Guo, H.; Han, Y.; Wu, M.; Wang, Q.; Li, M.; Chen, Y. From S,N-Heteroacene to Large Discotic Polycyclic Aromatic Hydrocarbons (PAHs): Liquid Crystal versus Plastic Crystalline Materials with Tunable Mechanochromic Fluorescence. Angew. Chem. Int. Ed. Engl. 2018, 57, 6161–6165. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  120. Hara, T.; Yoshizumi, H.; Watabe, T.; Ueda, A.; Seo, S. Organic Compound, Light-Emitting device, Light-Emitting Apparatus, Electronic Instrument, and Illumination Apparatus. Patent WO2020136496A1, 16 December 2019. [Google Scholar]
  121. Ujeed, A.; Liu, Q. Picene-Fused Quinoxaline and Diazoles: Synthesis and Characterizations. Russ. J. Gen. Chem. 2022, 92, 2536–2543. [Google Scholar] [CrossRef] [Scilit]
  122. Boerhan, R.; Sun, W.; Tian, N.; Wang, Y.; Lu, J.; Li, C.; Cheng, X.; Wang, X.; Zhou, Q. Fluorination on non-Photolabile dppz Ligands for Improving Ru(II) Complex-Based Photoactivated Chemotherapy. Dalton Trans. 2019, 48, 12177–12185. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  123. Sun, W.; Boerhan, R.; Tian, N.; Feng, Y.; Lu, J.; Wang, X.; Zhou, Q. Fluorination in Enhancing Photoactivated Antibacterial Activity of Ru(II) Complexes with Photo-Labile Ligands. RSC Adv. 2020, 10, 25364–25369. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  124. Roy, N.; Sen, U.; Chaudhuri, S.R.; Muthukumar, V.; Moharana, P.; Paira, P.; Bose, B.; Gauthaman, A.; Moorthy, A. Mitochondria Specific Highly Cytoselective Iridium(III)–Cp* Dipyridophenazine (dppz) Complexes as Cancer Cell Imaging Agents. Dalton Trans. 2021, 50, 2268–2283. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  125. Fu, C.; Lv, Q.; Fan, J.; Wu, S.; Lei, M.; Zhang, X.; Li, X.; Zhou, W.; Yu, Y.; Ren, W.; et al. Discovery of Polypyridyl Iridium(III) Complexes as Potent Agents Against Resistant Candida albicans. Eur. J. Med. Chem. 2022, 233, 114250. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  126. Zeiz, A.; Chayya, S.; Kassem, Z.; Hijazi, A.; Khawaja, G.; El-Dakdouki, M.H. Synthesis of Ruthenium Complexes and Assessing Their Anticancer and Antibacterial Effects. Farmacia 2023, 71, 1129–1142. [Google Scholar] [CrossRef] [Scilit]
  127. Zhou, Q.-H.; Du, K.; Qiang, L.; Guo, J.-H.; He, Q.; Wu, Y.; Tang, Q.; Shen, W.; Gong, C.-B. Photophysical, Electrochemical and Electrochromic Behavior of Transition Metal Complexes with 1,10-Phenanthroline Ligands. Dye. Pigment. 2023, 219, 111645. [Google Scholar] [CrossRef] [Scilit]
  128. Aggarwal, P.; Chaudhary, A.; De, S.; Singh, R.G.; Rao, V.G. Long-Lived Charge Separation Enabled by Molecular Engineering of Phenazine-Based Hole Transport Materials. Small 2025, 21, 2501649. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  129. Wang, X.; Liu, X.; Tan, L. Comparative Studies on the Binding Interaction of Two Chiral Ru(II) Polypyridyl Complexes with Triple- and Double-Helical Forms of RNA. J. Inorg. Biochem. 2021, 214, 111301. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  130. Wang, X.; Liu, X.; Tan, L. Substituent Effects on the Interactions of Ruthenium(II) Polypyridyl complexes [Ru(bpy)2(6-R-dppz)]2+ (R = hydroxy and fluorine) with the RNA triplex Poly(rU)·Poly(rA) × Poly(rU). Polyhedron 2021, 202, 115196. [Google Scholar] [CrossRef] [Scilit]
  131. Li, R.; Ma, Y.; Hu, X.; Wu, W.; Wu, X.; Dong, C.; Shi, S.; Lin, Y. [Ru(phen)2podppz]2+ Significantly Inhibits Glioblastoma Growth in vitro and vivo with Fewer Side-Effects than Cisplatin. Dalton Trans. 2020, 49, 8864–8871. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  132. Wang, F.; Ma, S.; Feng, Y.; Liu, X.; Tan, L. Binding Propterties of Two Ru(II) Polypyridyl Complexes Containing dppz Units and Fluorine Groups with Poly(U)·Poly(A) ∗ Poly(U) Triplex. J. Inorg. Biochem. 2019, 197, 110705. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  133. Li, W.; Liu, X.; Tan, L.-F. Binding Properties of [Ru(phen)2(11-R-dppz)]2+ (R = F or CN) with Poly(A)•Poly(U) Duplex RNA. J. Inorg. Biochem. 2022, 232, 111833. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  134. Hao, J.; Zhang, H.; Tian, L.; Yang, L.; Zhou, Y.; Zhang, Y.; Liu, Y.; Xing, D. Evaluation of Anticancer Effects In Vitro of New Iridium(III) Complexes Targeting the Mitochondria. J. Inorg. Biochem. 2021, 221, 111465. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  135. De, S.; Sarkar, B.; Jadhav, G.R.; Ramasamy, S.K.; Banerjee, S.; Moorthy, A.; Paira, P.; Sk, A.K. Experimental and Theoretical Study on the Biomolecular Interaction of Novel Acenaphtho Quinoxaline and Dipyridophenazine Analogues. ChemistrySelect 2018, 3, 10593–10602. [Google Scholar] [CrossRef] [Scilit]
  136. Tan, Z.; Zhu, J.; Ni, W.; Liu, X.; Li, Y.; Tan, L. Binding Properties of Two Ruthenium(II) Polypyridyl Complexes [Ru(bpy)2(dppz-Br)]2+ and [Ru(dmb)2(dppz-Br)]2+ with the RNA Poly(U)•Poly(A)*Poly(U) Triplex. J. Biol. Inorg. Chem. 2019, 24, 721–731. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  137. Yuan, F.; Liu, X.; Tan, L. Binding Properties of Ruthenium(II) Complexes [Ru(phen)2(7-R-dppz)]2+ (R = Methyl or Bromine) toward Poly(U)•Poly(A) RNA Duplex. Int. J. Biol. Macromol. 2022, 209, 1648–1655. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  138. Lauria, T.; Slator, C.; McKee, V.; Müller, M.; Stazzoni, S.; Crisp, A.L.; Carell, T.; Kellett, A. A Click Chemistry Approach to Developing Molecularly Targeted DNA Scissors. Chem. Eur. J. 2020, 26, 16782–16792. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  139. Peng, X.; Liu, X.; Li, J.; Tan, L. RNA-Binding of Ru(II) Complexes [Ru(phen)2(7-OCH3-dppz)]2+ and [Ru(phen)2(7-NO2-dppz)]2+: The Former Serves as a Molecular “Light Switch” for poly(A)•poly(U). J. Inorg. Biochem. 2022, 237, 111991. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  140. Müller, C.; Kaufmann, M.; Brandon, M.P.; Cullen, A.A.; Dietzek-Ivanšić, B.; Pryce, M.T. New Twist on the Light-Switch Effect: Controlling the Fate of Excited States with pH in a 4-Hydroxy-thiazol-extended Ruthenium(II) Dppz Complex. J. Phys. Chem. A 2023, 127, 10613–10620. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  141. Li, H.; Cao, M.; Wang, R.; Xiong, P.; Liu, Y.; Zhang, L.; Zhang, L.; Zhang, L.; Chao, D.; Zhang, C. Design Strategy for Small-Molecule Organic Cathodes: Regulated Active Groups Enable High Capacity and Voltage in Aqueous and Seawater Aluminum Ion Batteries. Angew. Chem. Int. Ed. Engl. 2025, 64, e202508057. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  142. Wan, K.; Tan, L.; Wen, B. Effect of Solution Environment on the Binding Properties of Ruthenium(II) Complexes [Ru(bim)2(7-CH3-dppz)]2+ and [Ru(bim)2(dppx)]2+ with Double-Stranded RNA poly(A)·poly(U). Inorg. Chim. Acta 2025, 574, 122387. [Google Scholar] [CrossRef] [Scilit]
  143. Jiang, L.; Liu, X.; Tan, L. Synthesis and Characterization of Chiral Ru(II) Polypyridyl Complexes and Their Binding and Stabilizing Effects toward Triple-Helical RNA. J. Inorg. Biochem. 2020, 213, 111263. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  144. Ni, W.; Liu, X.; Tan, L. Binding Properties of Chiral Ruthenium(II) Complexes Λ- and Δ-[Ru(bpy)2dppz-11-CO2Me]2+ toward the Triplex RNA Poly(U)•Poly(A)*Poly(U). J. Inorg. Biochem. 2018, 186, 51–59. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  145. Obitz, D.; Miller, R.G.; Metzler-Nolte, N. Synthesis and DNA Interaction Studies of Ru(II) Cell Penetrating Peptide (CPP) Bioconjugates. Dalton Trans. 2021, 50, 13768–13777. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  146. Wang, H.; Liu, X.; Tan, L. A Naked-eye Colorimetric Molecular “Light Switch” Based on Ruthenium(II) Polypyridyl Complex [Ru(phen)2ttbd]2+ as Binder and Stabilizer for RNA Duplex and Triplex. Int. J. Biol. Macromol. 2022, 215, 571–578. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  147. Pashaei, B.; Shahroosvand, H.; Moharramnezhad, M.; Kamyabi, M.A.; Bakhshi, H.; Pilkington, M.; Nazeeruddin, M.K. Two in One: A Dinuclear Ru(II) Complex for Deep-Red Light-Emitting Electrochemical Cells and as an Electrochemiluminescence Probe for Organophosphorus Pesticides. Inorg. Chem. 2021, 60, 17040–17050. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  148. McLay, J.R.W.; Sutton, J.J.; Shillito, G.E.; Larsen, C.B.; Huff, G.S.; Lucas, N.T.; Gordon, K.C. Transitioning from Intraligand π,π* to Charge-Transfer Excited States Using Thiophene-Based Donor-Acceptor Systems. Inorg. Chem. 2021, 60, 130–139. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  149. Chen, F.; Ma, H.; Wen, G.; Wu, X.; Lin, X.; Li, D.; Wang, D.; Dao, A.; Huang, H.; Zhang, P. Regioisomerization Strategy in Iridium(III) Complexes Achieving Enhanced Type I Photosensitization and Tumor Photoimmunotherapy. J. Med. Chem. 2025, 68, 13019–13029. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  150. Zhao, B.; Wang, H.; Han, C.; Ma, P.; Li, Z.; Chang, P.; Xu, H. Highly Efficient Deep-Red Non-Doped Diodes Based on a T-Shape Thermally Activated Delayed Fluorescence Emitter. Angew. Chem. Int. Ed. Engl. 2020, 59, 19042–19047. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  151. García-López, V.; Milić, J.V.; Zalibera, M.; Neshchadin, D.; Kuss-Petermann, M.; Ruhlmann, L.; Nomrowski, J.; Trapp, N.; Boudon, C.; Gescheidt, G.; et al. Light-actuated Resorcin [4]arene Cavitands. Tetrahedron 2018, 74, 5615–5626. [Google Scholar] [CrossRef] [Scilit]
  152. Zhou, Y.; Bai, L.; Gu, Y.-Y.; Tian, L.; Yin, H.; Zhang, Y.-Y.; Zhang, H.-W.; Xing, D.-G.; Liu, Y.-J. Synthesis, Evaluation of Biological Activity Studies of Iridium(III) Complexes Against Human Gastric Carcinoma SGC-7901 Cells. Inorg. Chem. Commun. 2020, 118, 108012. [Google Scholar] [CrossRef] [Scilit]
  153. Yıldız, U.; Şengül, A.; Kandemir, I.; Cömert, F.; Akkoç, S.; Coban, B. The Comparative Study of the DNA Binding and Biological Activities of the Quaternized Dicnq as a Dicationic form and Its Platinum(II) Heteroleptic Cationic Complex. Bioorg. Chem. 2019, 87, 70–77. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  154. Wen, B.; Liu, X.; Tan, L. Binding and Stabilizating Effect of RNA Triplex Poly(U)·Poly(A)*Poly(U) by Enantiomers of Ruthenium(II) Polypyridyl Complex [Ru(bpy)2(dppx)]2+. J. Biol. Inorg. Chem. 2023, 28, 509–517. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  155. Bhatia, H.; Guo, J.; Savory, C.N.; Rush, M.; James, D.I.; Dey, A.; Chen, C.; Bučar, D.-K.; Clarke, T.M.; Scanlon, D.O.; et al. Exploring Bismuth Coordination Complexes as Visible-Light Absorbers: Synthesis, Characterization, and Photophysical Properties. Inorg. Chem. 2024, 63, 416–430. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  156. Wang, H.; Zhao, B.; Ma, P.; Li, Z.; Wang, X.; Zhao, C.; Fan, X.; Tao, L.; Duan, C.; Zhang, J.; et al. A Red Thermally Activated Delayed Fluorescence Emitter Employing Dipyridophenazine with a Gradient Multi-Inductive Effect to Improve Radiation Efficiency. J. Mater. Chem. C 2019, 7, 7525–7530. [Google Scholar] [CrossRef] [Scilit]
  157. Pavlović, M.; Nikolić, S.; Gligorijević, N.; Dojčinović, B.; Aranđelović, S.; Grgurić-Šipka, S.; Radulović, S. New Organoruthenium Compounds with Pyrido[2′,3′:5,6]pyrazino[2,3-f][1,10]phenanthroline: Synthesis, Characterization, Cytotoxicity, and Investigation of Mechanism of Action. J. Biol. Inorg. Chem. 2019, 24, 297–310. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  158. Chen, P.; Liu, X.; Tan, L. Insight into the Intercalating Ligands Affecting the Interactions of Ruthenium(II) Polypyridyl Complexes with RNA Poly(A)*Poly(U). Polyhedron 2023, 240, 116460. [Google Scholar] [CrossRef] [Scilit]
  159. Yuan, G.; Yang, Y.-Z.; Wang, D.-H.; Xie, F.-M.; Zhang, Q.; Li, Y.-Q.; Hu, Y.-Y.; Tang, J.-X.; Zhao, X. Positional Isomeric Effect: A Simple and Feasible Strategy for Constructing Efficient Red TADF Materials. Dye. Pigment. 2024, 224, 111981. [Google Scholar] [CrossRef] [Scilit]
  160. Yang, H.-Y.; Zhang, H.-Y.; Zhang, M.; Zhuo, H.; Wang, H.; Lin, H.; Tao, S.-L.; Zheng, C.-J.; Zhang, X.-H. Simultaneously Optimizing Radiative Decay and Up-Conversion of Triphenylamine-Based Thermally Activated Delayed Fluorescence Emitters to Achieve Efficient Deep-Red Organic Light-Emitting Diodes. Chem. Eng. J. 2023, 468, 143721. [Google Scholar] [CrossRef] [Scilit]
  161. Devi, L.R.; Raza, K.; Musib, D.; Ramu, V.; Devi, J.; Roy, M. Nucleus Targeting Anthraquinone-Based Copper (II) Complexes as the Potent PDT Agents: Synthesis, Photo-Physical and Theoretical Evaluation. Inorg. Chim. Acta 2020, 500, 119208. [Google Scholar] [CrossRef] [Scilit]
  162. Feng, Y.; Liu, X.; Ma, S.; Wang, F.; Tan, L. Ruthenium(II) Polypyridyl Complex [Ru(phen)2dppz-idzo]2+ as a Colorimetric Molecular “Light Switch” and Powerful Stabilizer for the RNA Triplex Poly(U)·Poly(A)*Poly(U). Spectrochim. Acta A Mol. Biomol. Spectrosc. 2019, 212, 240–245. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  163. Abulhasanov, B.; Yildiz, U.; Akkoç, S.; Coban, B. Synthesis, Characterization, Duplex-DNA Interactions, and Anticancer Activities of Novel Octahedral [Ni(phen)2(dppz-idzo)]2+ and [Co(phen)2(dppz-idzo)]3+ Complexes. Appl. Organomet. Chem. 2020, 34, e5866. [Google Scholar] [CrossRef] [Scilit]
  164. Isakov, D.; Schmid, M.-A.; Nauroozi, D.; Rau, S.; Tschierlei, S. Prolonged Luminescence Lifetime of a Dual Emissive Ruthenium Dipyridophenazine-Type Complex in Aprotic and Protic Solvents. Inorg. Chem. 2021, 60, 14002–14010. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  165. Zhang, L.; Zhang, Y.; Zhao, M.; Ding, K.; Liu, H.; Wang, Y. Enhanced π-Conjugation and Multi-Electron Transfer Organic Cathodes Enabled High-Performance Zinc-Ion Storage. J. Colloid. Interface Sci. 2026, 702, 138818. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  166. Wei, T.; Zeng, Y.; Hong, L.; Zhang, H.; Wang, G.; Wang, S. Experimental and Theoretical Investigations of the Optoelectronic Properties of a 1,2,5-Oxadiazolo-fused Phenanthroline. Monatsh. Chem. 2018, 149, 1753–1758. [Google Scholar] [CrossRef] [Scilit]
  167. Wang, L.; Cui, P.; Lystrom, L.; Lu, J.; Kilinaa, S.; Sun, W. Heteroleptic Cationic Iridium(III) Complexes Bearing Phenanthroline Derivatives with Extended π-Conjugation as Potential Broadband Reverse Saturable Absorbers. New J. Chem. 2020, 44, 456–465. [Google Scholar] [CrossRef] [Scilit]
  168. Liang, J.-X.; Tang, Y.; Wang, X.; Zhang, K.; Shih, Y.-W.; Chen, C.-H.; Chiu, T.-L.; Li, P.J.; Lee, J.-H.; Wang, C.-K.; et al. Highly Efficient Near-Infrared Thermally Activated Delayed Fluorescence Organic Light-Emitting Diodes with Emission Beyond 800 nm. J. Mater. Chem. C 2023, 11, 6981–6988. [Google Scholar] [CrossRef] [Scilit]
  169. Toupin, N.P.; Nadella, S.; Steinke, S.J.; Turro, C.; Kodanko, J.J. Dual-Action Ru(II) Complexes with Bulky π-Expansive Ligands: Phototoxicity without DNA Intercalation. Inorg. Chem. 2020, 59, 3919–3933. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  170. Soulis, K.; Gourlaouen, C.; Daniel, C.; Quatela, A.; Odobel, F.; Blart, E.; Pellegrin, Y. New Luminescent Copper(I) Complexes with Extended π-Conjugation. Polyhedron 2018, 140, 42–50. [Google Scholar] [CrossRef] [Scilit]
  171. Wang, H.; Xie, G.; Zhao, B.; Chang, P.; Man, Y.; Duan, J.; Lu, J.; Han, C.; Xu, H. Near-infrared OLEDs with high radiance of ∼105 mW Sr−1 m−2 for single-wavelength oxygen saturation detection. Chem. Eng. J. 2023, 477, 147218. [Google Scholar] [CrossRef] [Scilit]
  172. Bai, Z.; Wang, J.; Zou, P.; Jiang, R.; Yang, D.; Ma, D.; Tang, B.Z.; Zhao, Z. Creating Efficient Red Thermally Activated Delayed Fluorescence Materials with Cyano-Substituted 11,12-Diphenyldipyrido[3,2-a:2′,3′-c]phenazine Acceptors. Chem. Eur. J. 2024, 30, e202303990. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  173. Bhadke, A.; Lambud, S.; Siddiqui, Z.A.; Bommera, A.; Sekar, N.; More, S. Dual State Emissive Pyrene-Fused Benzopyrazaacenes and Their Solvatochromic Behaviour. J. Mol. Struct. 2024, 1314, 138796. [Google Scholar] [CrossRef] [Scilit]
  174. Wang, Q.; Gao, W.; Chen, Y.; Wang, X.; Zeng, J.; Liu, Y.; Ran, H.; Hu, Z.; Bai, J.; Feng, X.; et al. Pyrene-fused Dibenzoazatetracenes: Synthesis, Crystal Structures, Photophysical Properties and their Morphologies. Asian J. Org. Chem. 2021, 10, 233–240. [Google Scholar] [CrossRef] [Scilit]
  175. Lei, W.; Li, X. Nitrogen-Containing Fused Heterocyclic Compound and Electroluminescent Device. Patent CN118239895A, 25 March 2024. [Google Scholar]
  176. Song, X.; Zhao, J.; Zhang, W.; Chen, L. Novel n-Channel Organic Semiconductor Based on Pyrene-Phenazine Fused Monoimide and Bisimides. Chin. Chem. Lett. 2018, 29, 331–335. [Google Scholar] [CrossRef] [Scilit]
  177. Follana-Berná, J.; Dawson, A.; Kaswan, R.R.; Seetharaman, S.; Karr, P.A.; Sastre-Santos, Á.; D’Souza, F. π-Extended Pyrazinepyrene-Fused Zinc Phthalocyanines: Synthesis and Excited-State Charge Separation Involving Coordinated C60. J. Phys. Chem. A. 2023, 127, 6191–6203. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  178. Fernandes, S.P.S.; Frey, L.; Cid-Seara, K.M.; Oliveira, O.; Guldris, N.; Carbó-Argibay, E.; Rodríguez-Abreu, C.; Kolen’ko, Y.V.; Silva, A.M.S.; Medina, D.D.; et al. A Post-Synthetic Modification Strategy for the Synthesis of Pyrene-Fused Azaacene Covalent Organic Frameworks. Microporous Mesoporous Mater. 2022, 343, 112162. [Google Scholar] [CrossRef] [Scilit]
  179. Yang, T.; Liang, B.; Cheng, Z.; Li, C.; Lu, G.; Wang, Y. Construction of Efficient Deep-Red/Near-Infrared Emitter Based on a Large π-Conjugated Acceptor and Delayed Fluorescence OLEDs with External Quantum Efficiency of over 20%. J. Phys. Chem. C 2019, 123, 18585–18592. [Google Scholar] [CrossRef] [Scilit]
  180. Sun, W.; Yang, Y.; Tian, X.; Yuan, L.; Wang, Y.; Dou, C. A Combination of B- and N-Doped π-Systems Enabling Systematic Tuning of Electronic Structures and Properties. Chem. Eur. J. 2023, 29, e202302459. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  181. Shang, H.; Zhou, W.; Wu, X.; Xiao, J.; Song, Y. Synthesis, Photophysics and Optical Limiting Properties of Functionalized Benzofuran Derivatives. Asian J. Org. Chem. 2023, 12, e202200664. [Google Scholar] [CrossRef] [Scilit]
  182. Jakubec, M.; Hansen-Troøyen, S.; Císařová, I.; Sýkora, J.; Storch, J. Photochemical Oxidation Specific to Distorted Aromatic Amines Providing ortho-Diketones. Org. Lett. 2020, 22, 3905–3910. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  183. Zhao, T.; Cao, C.; Wang, H.; Shen, X.; Lai, H.; Zhu, Y.; Chen, H.; Han, L.; Rehman, T.; He, F. Highly Efficient All-Polymer Solar Cells from a Dithieno[3,2-f:2′,3′-h]quinoxaline-Based Wide Band Gap Donor. Macromolecules 2021, 54, 11468–11477. [Google Scholar] [CrossRef] [Scilit]
  184. Zhang, C.; Tu, X.; Luo, Y.; Hai, Y.; Yao, X.; Xian, K.; Dela Peña, T.A.; Li, Y.; Li, Y.; Li, M.; et al. Enhanced Molecular Planarity for High-Performance Photodetectors: Effect of Backbone Conformation via Alkyl Substitution Position Control in Dithienoquinoxaline-Based Conjugated Polymers. Chem. Eng. J. 2024, 488, 150566. [Google Scholar] [CrossRef] [Scilit]
  185. Huang, L.; Ma, P.; Deng, G.; Zhang, K.; Ou, T.; Lin, Y.; Wong, M.S. Novel Electron-Deficient Quinoxalinedithienothiophene- and Phenazinedithienothiophene-Based Photosensitizers: The Effect of Conjugation Expansion on DSSC Performance. Dye. Pigment. 2018, 159, 107–114. [Google Scholar] [CrossRef] [Scilit]
  186. Yadav, D.; Shukla, G.; Ansari, M.A.; Srivastava, A.; Singh, M.S. Chemoselective One-Pot Access to Benzo[e]indole-4,5-diones and Naphtho[2,1-b]thiophene-4,5-diones via Copper-Catalyzed Oxidative [3+2] Annulation of α-Oxoketene N,S-Acetals/β-Ketothioamides with α-/β-Naphthols. Tetrahedron 2018, 74, 5920–5931. [Google Scholar] [CrossRef] [Scilit]
  187. Lücht, A.; Jones, P.G.; Werz, D.B. Reactions of 3,3′-Linked Bispyrroles with Carbon Electrophiles. Eur. J. Org. Chem. 2019, 2019, 5254–5260. [Google Scholar] [CrossRef] [Scilit]
  188. Shukla, G.; Srivastava, A.; Yadav, D.; Singh, M.S. Copper-Catalyzed One-Pot Cross-Dehydrogenative Thienannulation: Chemoselective Access to Naphtho[2,1-b]thiophene-4,5-diones and Subsequent Transformation to Benzo[a]thieno[3,2-c]phenazines. J. Org. Chem. 2018, 83, 2173–2181. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  189. Guo, H.; Zhang, H.; Shen, C.; Zhang, D.; Liu, S.; Wu, Y.; Zhu, W.-H. A Coplanar π-Extended Quinoxaline Based Hole-Transporting Material Enabling over 21 % Efficiency for Dopant-Free Perovskite Solar Cell. Angew. Chem. Int. Ed. Engl. 2021, 60, 2674–2679. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  190. Qu, C.; Wang, H.; Man, Y.; Li, Z.; Ma, P.; Chang, P.; Li, X.; Han, C.; Pang, Y.; Xu, H. Asymmetric Intramolecular Charge Transfer Enables Highly Efficient Red Thermally Activated Delayed Fluorescent Emitters. Chem. Eng. J. 2023, 457, 141061. [Google Scholar] [CrossRef] [Scilit]
  191. Li, Y.; Liu, S.; Ni, H.; Zhang, H.; Zhang, H.; Chuah, C.; Ma, C.; Wong, K.S.; Lam, J.W.Y.; Kwok, R.T.K.; et al. ACQ-to-AIE Transformation: Tuning Molecular Packing by Regioisomerization for Two-Photon NIR Bioimaging. Angew. Chem. Int. Ed. Engl. 2020, 59, 12822–12826. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  192. Li, Z.; Chen, C.; Wang, M.; Tang, Z.; Ma, Z. Conjugated Polymer Material Containing Benzodithiophene-4,5-diketone As Well As Preparation Method and Application of Conjugated Polymer Material. Patent CN115386068A, 18 August 2022. [Google Scholar]
  193. Tian, D.; Ma, Z.; Gu, L.; Zhou, C.; Li, C.; Wang, Z.; Wang, H. Isomerically Fused Benzo[i]dithiophenephenazine and Benzo[i]diselenophenephenazine: Synthesis, Crystal Packing, and Density Functional Theory Calculations. Cryst. Growth Des. 2020, 20, 4479–4490. [Google Scholar] [CrossRef] [Scilit]
  194. Annadhasan, M.; Agrawal, A.R.; Bhunia, S.; Pradeep, V.V.; Zade, S.S.; Reddy, C.M.; Chandrasekar, R. Mechanophotonics: Flexible Single-Crystal Organic Waveguides and Circuits. Angew. Chem. Int. Ed. Engl. 2020, 59, 13852–13858. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  195. Gao, Y.; An, C.; Wang, Z.; Sun, Y.; Wei, Z.; Guo, F.; Yang, Y.; Zhao, L.; Zhang, Y. Efficient Post-Treatment-Free Polymer Solar Cells from Indacenodithiophene and Fluorinated Quinoxaline-Based Conjugated Polymers. Dye. Pigment. 2018, 154, 164–171. [Google Scholar] [CrossRef] [Scilit]
  196. Cardeynaels, T.; Paredis, S.; Deckers, J.; Brebels, S.; Vanderzande, D.; Maes, W.; Champagne, B. Finding the Optimal Exchange–Correlation Functional to Describe the Excited State Properties of Push–Pull Organic Dyes Designed for Thermally Activated Delayed Fluorescence. Phys. Chem. Chem. Phys. 2020, 22, 16387–16399. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  197. Wang, Z.; Xu, C.; Yang, Z.; Zou, Y.; Zhang, K.; Gao, P.; Xu, W.; Li, G.; Chen, J.; Liang, M. Dithieno[3,2-a:2′,3′-c]phenazine Based Hole-transporting Materials for Efficient Perovskite Solar Cells: Effects of Donors Numbers. Dye. Pigment. 2023, 211, 111066. [Google Scholar] [CrossRef] [Scilit]
  198. Wang, Z.; Wang, Z.; Ma, Z.; Chen, R.; Wang, T.; Kang, J.; Hu, G.; Zong, X. Efficient Interfacial Optimization of NiOx-Based Perovskite Solar Cells via a Butterfly-Structured Semiconductor. New J. Chem. 2025, 49, 204–212. [Google Scholar] [CrossRef] [Scilit]
  199. Fuchs, K.; Medina Rivero, S.; Weidlich, A.; Rominger, F.; Israel, N.; Popov, A.A.; Dreuw, A.; Freudenberg, J.; Casado, J.; Bunz, U.H.F. Dimerization of a Reactive Azaacene Diradical: Synthesis of a Covalent Azaacene Cage. Angew. Chem. Int. Ed. Engl. 2023, 62, e202305712. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  200. Song, X.; Yu, H.; Zhang, Y.; Miao, Y.; Ye, K.; Wang, Y. Controllable Morphology and Self-Assembly of One-Dimensional Luminescent Crystals Based on Alkyl-Fluoro-Substituted Dithienophenazines. CrystEngComm 2018, 20, 1669–1678. [Google Scholar] [CrossRef] [Scilit]
  201. Fuchs, K.; Oberhof, N.; Sauter, G.; Pollien, A.; Brödner, K.; Rominger, F.; Freudenberg, J.; Dreuw, A.; Tegeder, P.; Bunz, U.H.F. Azaacene Diradicals Based on Non-Kekulé Meta-Quinodimethane with Large Two-Photon Cross-Sections in the Infrared Spectral Region. Angew. Chem. Int. Ed. Engl. 2024, 63, e202406384. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  202. Zhang, Z.; Feng, W.; Zhang, Y.; Yuan, S.; Bai, Y.; Wang, P.; Yao, Z.; Li, C.; Duan, T.; Wan, X.; et al. Delicate Chemical Structure Regulation of Nonfullerene Acceptor for Efficient and Large Thickness Organic Solar Cells. Sci. China Chem. 2024, 67, 1596–1604. [Google Scholar] [CrossRef] [Scilit]
  203. Qu, W.; Yuan, W.; Li, M.; Chen, Y. A Hexaazatriphenylene Fused Large Discotic Polycyclic Aromatic Hydrocarbon with Selective and Sensitive Metal-Ion Sensing Properties. Chin. Chem. Lett. 2021, 32, 3837–3840. [Google Scholar] [CrossRef] [Scilit]
  204. Kuklin, S.; Keshtov, M.; Konstantinov, I.; Godovskiy, D.; Zuo, Y.; Ostapov, I.; Khokhlov, A.; Makhayeva, E. New Quinoxaline-Containing Monomers for Narrow Bandgap Polymers. Dokl. Akad. Nauk 2018, 482, 46–51. [Google Scholar] [CrossRef] [Scilit]
  205. Keshtov, M.L.; Kuklin, S.A.; Konstantinov, I.O.; Ostapov, I.E.; Godovsky, D.Y.; Makhaeva, E.E.; Xie, Z.; Sharma, G.D. Conjugated Random Terpolymers Based on Benzodithiophene, Diketopyrrolopyrrole, and 8,10-Bis(thiophen-2-yl)-2,5-di(nonadecan-3-yl)bis[1,3]thiazolo[4,5-f:5′,4′-h]thieno[3,4-b]quinoxaline for Efficient Polymer Solar Cell. J. Polym. Sci. Part A Polym. Chem. 2019, 57, 1478–1485. [Google Scholar] [CrossRef] [Scilit]
  206. Qiu, D.; Zhang, L.; Zhang, H.; Tang, A.; Zhang, J.; Wei, Z.; Lu, K. Elucidating the Effects of Bromine Substitution in Asymmetric Quinoxaline Central Core-Based Non-Fullerene Acceptors on Molecular Stacking and Photovoltaic performances. J. Mater. Chem. A 2025, 13, 4237–4246. [Google Scholar] [CrossRef] [Scilit]
  207. Kang, X.; Bi, F.; Adeoba, A.A.; Makhmanov, U.K.; Sun, M.; Bao, X. Profound Influences of Two-Dimensional Side Chains Regional Transfer on Crystallinity and Photovoltaic Performance of Donor Polymers. Macromolecules 2024, 57, 7820–7829. [Google Scholar] [CrossRef] [Scilit]
  208. Kong, M.; Feng, X.; Li, J.; Hu, Z.-B.; Wang, J.; Song, X.-J.; Jing, Z.-Y.; Zhang, Y.-Q.; Song, Y. Structurally Modulated Single-Ion Magnets of Mononuclear β-Diketone Dysprosium(III) Complexes. Dalton Trans. 2020, 49, 14931–14940. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  209. Hu, W.; Gao, J.; Shi, B.; Xia, Z.; Xiao, Y.; Geng, Y.; Lü, C. Pyrazino[2,3-f][1,10]phenanthroline Derivatives as Robust Photocatalysts Ena-bling ppm-Level Organocatalyzed Photoinduced Electron/Energy Transfer Reversible Addition–Fragmentation Chain Transfer Polymerization. ACS Catal. 2024, 14, 8148–8159. [Google Scholar] [CrossRef] [Scilit]
  210. Hau, K.I.; Lo, K.C.; Xiong, W.; Du, L.; Chan, W.K. Synthesis of Metallo-conjugated Copolymer with Electron Deficient Main Chain and the Formation of Polymer–Carbon Nanotube Hybrids. J. Inorg. Organomet. Polym. 2020, 30, 243–253. [Google Scholar] [CrossRef] [Scilit]
  211. Moshkina, T.N.; Nosova, E.V.; Kopotilova, A.E.; Lipunova, G.N.; Valova, M.S.; Sadieva, L.K.; Kopchuk, D.S.; Slepukhin, P.A.; Zaleśny, R.; Ośmiałowski, B.; et al. Synthesis and Photophysical Studies of Novel V-Shaped 2,3-Bis{5-aryl-2-thienyl}(dibenzo[f,h])quinoxalines. Asian J. Org. Chem. 2020, 9, 673–681. [Google Scholar] [CrossRef] [Scilit]
  212. Moshkina, T.N.; Kopotilova, A.E.; Gazizov, D.A.; Valieva, M.I.; Starnovskaya, E.S.; Kalinichev, A.A.; Kopchuk, D.S.; Nosova, E.V.; Charushin, V.N. Modified 2,3-bis(thienyl)quinoxaline fluorophores as potential chemosensors. Russ. Chem. Bull. 2024, 73, 1745–1754. [Google Scholar] [CrossRef] [Scilit]
  213. Gao, Z.; Zhang, C.; Lin, C.; Lei, S.; Wang, Y.; Zhang, M. Novel Organic Electroluminescent Material Containing Pyrazine-Ring as Well as Preparation Method and Application Thereof. Patent CN107987029A, 12 November 2017. [Google Scholar]
  214. Yang, W.; Ning, W.; Gong, S.; Yang, C. Deep-Red Thermally Activated Delayed Fluorescence Emitters Based on a Phenanthroline-Containing Planar Acceptor. Dye. Pigment. 2021, 192, 109474. [Google Scholar] [CrossRef] [Scilit]
  215. González-Núñez, R.; Alonso-Navarro, M.J.; Suárez-Blas, F.; Gala, E.; Ramos, M.M.; Segura, J.L.; Ponce Ortiz, R. Tuning the Charge Stabilization and Transport in Naphthalimide-Based Semiconductors via a Fused-Ring and Core-Engineering Strategy. Mater. Chem. Front. 2024, 8, 1981–1992. [Google Scholar] [CrossRef] [Scilit]
  216. Im, Y.-K.; Lee, D.-G.; Noh, H.-J.; Yu, S.-Y.; Mahmood, J.; Lee, S.-Y.; Baek, J.-B. Crystalline Porphyrazine-Linked Fused Aromatic Networks with High Proton Conductivity. Angew. Chem. Int. Ed. Engl. 2022, 61, e202203250. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  217. Sakai, N.; Tamura, T.; Yanase, T.; Nagahama, T.; Shimada, T. Single Crystal Growth, Structural Analysis and Electronic Band Structure of a Nitrogen-Containing Polyacene Benzo[i]benzo[6′,7′]quinoxalino[2′,3′:9,10]phenanthro[4,5-abc]phenazine. Jpn. J. Appl. Phys. 2019, 58, SBBG08. [Google Scholar] [CrossRef] [Scilit]
  218. Kohl, B.; Baumgärtner, K.; Rominger, F.; Mastalerz, M. Quinoxalinophenanthrophenazines (QPPs) and Hexabenzoovalenes (HBOs)—Proving the Solubility Enhancement by Triptycene End-Capping. Eur. J. Org. Chem. 2019, 2019, 4891–4896. [Google Scholar] [CrossRef] [Scilit]
  219. Ueberricke, L.; Mizioch, D.; Ghalami, F.; Mildner, F.; Rominger, F.; Oeser, T.; Elstner, M.; Mastalerz, M. Quinoxalinophenanthrophenazine Based Cruciforms. Eur. J. Org. Chem. 2021, 2021, 4816–4823. [Google Scholar] [CrossRef] [Scilit]
  220. Min, Y.; Dou, C.; Tian, H.; Liu, J.; Wang, L. Isomers of B←N-Fused Dibenzo-azaacenes: How B←N Affects Opto-electronic Properties and Device Behaviors? Chem. Eur. J. 2021, 27, 4364–4372. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  221. Min, Y.; Dou, C.; Tian, H.; Geng, Y.; Liu, J.; Wan, L. n-Type Azaacenes Containing B←N Units. Angew. Chem. Int. Ed. Engl. 2018, 57, 2000–2004. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  222. Min, Y.; Dou, C.; Liu, D.; Dong, H.; Liu, J. Quadruply B←N-Fused Dibenzo-azaacene with High Electron Affinity and High Electron Mobility. J. Am. Chem. Soc. 2019, 141, 17015–17021. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  223. Min, Y.; Cao, X.; Tian, H.; Liu, J.; Wang, L. B←N-Incorporated Dibenzo-azaacene with Selective Near-Infrared Absorption and Visible Transparency. Chem. Eur. J. 2021, 27, 2065–2071. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  224. Xiang, G.; He, X.; Liu, Y.; Lian, H.; Zhang, C.; Peng, J. Quinoxaline-Based Conjugated Microporous Polymer Photoelectrochemical Sensor for the Sensitive Detection of Dopamine. J. Electrochem. Soc. 2022, 169, 127505. [Google Scholar] [CrossRef] [Scilit]
  225. Nakashima, K.; Shimizu, T.; Kamakura, Y.; Hinokimoto, A.; Kitagawa, Y.; Yoshikawa, H.; Tanaka, D. A New Design Strategy for Redox-Active Molecular Assemblies with Crystalline Porous Structures for Lithium-Ion Batteries. Chem. Sci. 2020, 11, 37–43. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  226. Pickhardt, W.; Wohlgemuth, M.; Grätz, S.; Borchardt, L. Mechanochemically Assisted Synthesis of Hexaazatriphenylenehexacarbonitrile. J. Org. Chem. 2021, 86, 14011–14015. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  227. Hinokimoto, A.; Ono, T.; Fujiwara, M.; Mori, H.; Akiyoshi, R.; Nakamura, S.; Tsutsumi, O.; Saeki, A.; Kitagawa, Y.; Horike, S.; et al. Synthesis and Strong π–π Interaction of Hexaazatriphenylene Derivatives with Alternating Electron-Withdrawing and -Donating Groups. Chem. Asian J. 2022, 17, e202200225. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  228. Akiyoshi, R.; Fujiwara, M.; Kamakura, Y.; Shimizu, T.; Inoue, R.; Morisaki, Y.; Saeki, A.; Yoshikawa, H.; Tanaka, D. Effect of a One-Dimensional Columnar Structure on the Cathode Active Material Performance of Single-Component Hexaazatriphenylene Derivatives. ACS Appl. Energy Mater. 2022, 5, 12760–12767. [Google Scholar] [CrossRef] [Scilit]
  229. Zhou, K.; Liu, X.; Chen, X.; Su, L.; Yang, H.; Yang, B.; Liu, Q. High-Performance Aqueous Zinc-Ion Batteries Based on an Organic Compound with Multiple Active Groups and Hydrogen Bonds. Energy Fuels 2025, 39, 7576–7585. [Google Scholar] [CrossRef] [Scilit]
  230. Wang, J.; Tee, K.; Lee, Y.; Riduana, S.N.; Zhang, Y. Hexaazatriphenylene Derivatives/GO Composites as Organic Cathodes for Lithium Ion Batteries. J. Mater. Chem. A 2018, 6, 2752–2757. [Google Scholar] [CrossRef] [Scilit]
  231. Wu, W.-H.; Huang, M.-J.; Zeng, Q.; Xian, W.-R.; Liao, W.-M.; He, J. Electrical and Magnetic Properties of a Radical-Based Co(II) Coordination Complex with C–H···π and π···π Supramolecular Interactions. Inorg. Chem. Commun. 2019, 103, 149–153. [Google Scholar] [CrossRef] [Scilit]
  232. Morawski, O.; Karpiuk, J.; Sobolewski, A.L.; Gawryś, P. Aggregation Controlled Photoluminescence of Hexaazatri-Naphthylene (HATN)—An Experimental and Theoretical study. Phys. Chem. Chem. Phys. 2020, 22, 15437–15447. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  233. Sun, G.; Yang, B.; Chen, X.; Wei, Y.; Yin, G.; Zhang, H.; Liu, Q. Aqueous zinc batteries using N-containing organic cathodes with Zn2+ and H+ Co-uptake. Chem. Eng. J. 2022, 431, 134253. [Google Scholar] [CrossRef] [Scilit]
  234. Xiao, Y.-Q.; Shang, P.; Yang, G.-K.; Pu, X.-Q.; Jiang, K.-W.; Jiang, Z.-W.; Wu, C.; Gui, L.-C.; Wang, J.-P.; Jiang, X.-F. Ligand Conformation Directed Self-Assembly of Heteroleptic Cu(I) Complexes and Luminescent Sensing Properties for Zn2+. J. Solid State Chem. 2024, 330, 124464. [Google Scholar] [CrossRef] [Scilit]
  235. Yang, Z.; Meng, P.; Jiang, M.; Zhang, X.; Zhang, J.; Fu, C. Intermolecular Hydrogen Bonding Networks Stabilized Organic Supramolecular Cathode for Ultra-High Capacity and Ultra-Long Cycle Life Rechargeable Aluminum Batteries. Angew. Chem. Int. Ed. Engl. 2024, 63, e202403424. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  236. Wang, J.; Lee, Y.; Tee, K.; Riduana, S.N.; Zhang, Y. A Nanoporous Sulfur-Bridged Hexaazatrinaphthylene Framework as an Organic Cathode for Lithium Ion Batteries with Well-Balanced Electrochemical Performance. Chem. Commun. 2018, 54, 7681–7684. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  237. Tahir, N.; Wang, G.; Onyshchenko, I.; De Geyter, N.; Leus, K.; Morent, R.; Van der Voort, P. High-Nitrogen Containing Covalent Triazine Frameworks as Basic Catalytic Support for the Cu-Catalyzed Henry Reaction. J. Catal. 2019, 375, 242–248. [Google Scholar] [CrossRef] [Scilit]
  238. Wang, G.; Tahir, N.; Onyshchenko, I.; De Geyter, N.; Morent, R.; Leus, K.; Van Der Voort, P. Novel Hexaazatrinaphthalene-Based Covalent Triazine Frameworks as High-Performance Platforms for Efficient Carbon Capture and Storage. Microporous Mesoporous Mater. 2019, 290, 109650. [Google Scholar] [CrossRef] [Scilit]
  239. Huang, Q.; Zhu, J.-J.; Song, L.; Shang, P.; Jiang, X.-F. Highly Efficient Azide-Alkyne Cycloaddition over CuI-Modified Covalent Triazine Frameworks in Water. Microporous Mesoporous Mater. 2022, 345, 112261. [Google Scholar] [CrossRef] [Scilit]
  240. Chola, N.M.; Nagarale, R.K. Quinoxaline Derivatives as Cathode for Aqueous Zinc Battery. J. Solid State Electrochem. 2024, 28, 419–431. [Google Scholar] [CrossRef] [Scilit]
  241. Menart, S.; Pirnat, K.; Pahovnik, D.; Dominko, R. Triquinoxalinediol as Organic Cathode Material for Rechargeable Aqueous Zinc-Ion Batteries. J. Mater. Chem. A 2023, 11, 10874–10882. [Google Scholar] [CrossRef] [Scilit]
  242. Kim, S.-W.; Jung, H.; Okyay, M.S.; Noh, H.-J.; Chung, S.; Kim, Y.H.; Jeon, J.-P.; Wong, B.M.; Cho, K.; Seo, J.-M.; et al. Hexaazatriphenylene-Based Two-Dimensional Conductive Covalent Organic Framework with Anisotropic Charge Transfer. Angew. Chem. Int. Ed. Engl. 2023, 62, e202310560. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  243. Xu, S.; Wang, G.; Biswal, B.P.; Addicoat, M.; Paasch, S.; Sheng, W.; Zhuang, X.; Brunner, E.; Heine, T.; Berger, R.; et al. A Nitrogen-Rich 2D sp2-Carbon-Linked Conjugated Polymer Framework as a High-Performance Cathode for Lithium-Ion Batteries. Angew. Chem. Int. Ed. Engl. 2019, 58, 849–853. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  244. Pastoetter, D.L.; Liu, Y.; Addicoat, M.A.; Paasch, S.; Dianat, A.; Bodesheim, D.; Waentig, A.L.; Xu, S.; Borrelli, M.; Croy, A.; et al. Control of Crystallinity of Vinylene-Linked Two-Dimensional Conjugated Polymers by Rational Monomer Design. Chem. Eur. J. 2022, 28, e202104502. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  245. Sun, Z.; Yang, C.; Zhang, Y.; Zhang, J.; Chen, Z.; Peng, J.; Chen, C.; Yao, H.; Guan, S. Extended π-Conjugated N-Heteroaromatic Molecules for Fast-Charging and High Operating Voltage Aqueous Zinc-Ion Batteries. J. Colloid. Interface. Sci. 2025, 680, 456–463. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  246. Yang, P.; Wu, Z.; Wang, S.; Li, M.; Chen, H.; Qian, S.; Zheng, M.; Wang, Y.; Li, S.; Qiu, J.; et al. Synergetic Coupling of Redox-Active Sites on Organic Electrode Material for Robust and High-Performance Sodium-Ion Storage. Angew. Chem. Int. Ed. Engl. 2023, 62, e202311460. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  247. Fangmann, P.; Schmidtmann, M.; Beckhaus, R. Crystal Structures of 2,3,8,9,14,15-Hexamethyl-5,6,11,12,17,18-hexaazatrinaphthylene and 2,3,8,9,14,15-Hexaphenyl-5,6,11,12,17,18-hexazatri-naphthylene Dichloromethane Disolvate. Acta Crystallogr. E Crystallogr. Commun. 2018, 74, 167–171. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  248. Hisaki, I.; Suzuki, Y.; Gomez, E.; Ji, Q.; Tohnai, N.; Nakamura, T.; Douhal, A. Acid Responsive Hydrogen-Bonded Organic Frameworks. J. Am. Chem. Soc. 2019, 141, 2111–2121. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  249. Zhai, Y.; Li, H.; Ma, Q.; Wang, R.; Zhang, L.; Zhang, C. Construction of Fully Conjugated Pyrazine Derivative Organic Cathode for High-Rate and Long-Lifetime Lithium-Ion Batteries. Ionics 2023, 29, 1301–1310. [Google Scholar] [CrossRef] [Scilit]
  250. Wu, M.-S.; Luu, N.T.H.; Chen, T.-H.; Lyu, H.; Huang, T.-W.; Dai, S.; Sun, X.-G.; Ivanov, A.S.; Lee, J.-C.; Popovs, I.; et al. Supramolecular Self-Assembled Multi-Electron-Acceptor Organic Molecule as High-Performance Cathode Material for Li-Ion Batteries. Adv. Energy Mater. 2021, 11, 2100330. [Google Scholar] [CrossRef] [Scilit]
  251. An, Y.; Liu, Y.; Tan, S.; Xiong, F.; Liao, X.; An, Q. Dual Redox Groups Enable Organic Cathode Material with a High Capacity for Aqueous Zinc-Organic Batteries. Electrochim. Acta 2022, 404, 139620. [Google Scholar] [CrossRef] [Scilit]
  252. Huang, L.; Li, J.; Gao, X.; Wang, J.; Lv, H.; Xie, H.; Liu, Y.; Gu, T.; Wang, G. Realizing High-Performance of Quinone-Based Cathode via Multiple Active Centers for Aqueous Zinc Ion Batteries. J. Power Sources 2024, 591, 233896. [Google Scholar] [CrossRef] [Scilit]
  253. Zhai, Y.; Ji, C.; Wang, R.; Ma, Q.; Zhang, L.; Li, H.; Zhang, C.; Zhang, Q. Fully Conjugated Anthraquinone-Quinoxaline Derivative Cathode Enabling a Superior Zn-Ion Storage at Extremely Low Temperature −50 °C. Adv. Energy Mater. 2025, 15, 2403011. [Google Scholar] [CrossRef] [Scilit]
  254. Geng, X.; Ma, H.; Wang, Z.; Yang, K.; Zhang, W.; Zhang, H.; Zhang, J.; Song, Y.; Jin, Y.; Wang, T.; et al. Revealing Active Sites Storage Mechanism of Organic C=O/C=N Compounds for Ultralong-Life Aqueous Zinc-Ion Batteries. Chem. Eng. J. 2025, 510, 161584. [Google Scholar] [CrossRef] [Scilit]
  255. Li, S.; Shang, J.; Li, M.; Xu, M.; Zeng, F.; Yin, H.; Tang, Y.; Han, C.; Cheng, H.-M. Design and Synthesis of a π-Conjugated N-Heteroaromatic Material for Aqueous Zinc-Organic Batteries with Ultrahigh Rate and Extremely Long Life. Adv. Mater. 2022, 35, e2207115. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  256. Niu, S.; Wang, Y.; Zhang, J.; Wang, Y.; Tian, Y.; Ju, N.; Wang, H.; Zhao, S.; Zhang, X.; Zhang, W.; et al. Engineering Low-Cost Organic Cathode for Aqueous Rechargeable Battery and Demonstrating the Proton Intercalation Mechanism for Pyrazine Energy Storage Unit. Small 2024, 20, 2309022. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  257. Hwang, J.-D.; Chen, P.-Y.; Ding, S.-W.; Ong, C.W. Effect of Noncovalent Dispersion of Poly(Ethylene Oxide) in Columnar Polyether-Based Discotic Liquid Crystal on the Ionic Conductivity and Dynamics of Lithium Ions. Crystals 2019, 9, 627. [Google Scholar] [CrossRef] [Scilit]
  258. Vázquez, D.; Comba, M.B.; Spanevello, R.A.; Libonatti, B.; Mangione, M.I. Insights into the Synthesis of Hexaaminobenzene Hydrochloride: An Entry to Hexaazatriphenylenes. J. Mol. Struct. 2022, 1254, 132385. [Google Scholar] [CrossRef] [Scilit]
  259. Hisaki, I.; Suzuki, Y.; Gomez, E.; Cohen, B.; Tohnai, N.; Douhal, A. Docking Strategy to Construct Thermostable, Single-Crystalline, Hydrogen-Bonded Organic Framework with High Surface Area. Angew. Chem. Int. Ed. Engl. 2018, 130, 12832–12837. [Google Scholar] [CrossRef] [Scilit]
  260. Zhang, X.; Fan, Y.; Zhan, T.-G.; Qi, Q.-Y.; Zhao, X. A Thiophene-Derived Hexaazatriphenylene (HAT) Fluorescent Sensor for the Selective Detection of Ag+ Ion. Tetrahedron Lett. 2021, 68, 152911. [Google Scholar] [CrossRef] [Scilit]
  261. Pyszka, I.; Jędrzejewska, B. Photoinitiation Abilities of Indeno- and Indoloquinoxaline Derivatives and Mechanical Properties of Dental Fillings Based on Multifunctional Acrylic Monomers and Glass Ionomer. Polymer 2023, 266, 125625. [Google Scholar] [CrossRef] [Scilit]
  262. Song, X.; Yang, X.; Song, J.; Li, M.; Li, X.; Wang, X.; Zhang, Y. Indoquinone Organic Compound and Application Thereof. Patent CN112552301A, 26 September 2019. [Google Scholar]
  263. Wang, D.; Li, Y.; Wang, X. Fluorescence Emission Material and Organic Light-Emitting Device Prepared from Fluorescence Emission Material. Patent CN111825687A, 20 July 2020. [Google Scholar]
  264. Zhou, P.; Pashaki, M.N.H.; Frey, H.-M.; Hauser, A.; Decurtins, S.; Cannizzo, A.; Feurer, T.; Häner, R.; Aschauer, U.; Liu, S.-X. Photoinduced Asymmetric Charge Trapping in a Symmetric Tetraazapyrene-fused Bis(tetrathiafulvalene) Conjugate. Chem. Sci. 2023, 14, 12715–12722. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  265. Yu, H.; Song, X.; Xie, N.; Wang, J.; Li, C.; Wang, Y. Reversible Crystal-to-Crystal Phase Transitions with High-Contrast Luminescent Alterations for a Thermally Activated Delayed Fluorescence Emitter. Adv. Funct. Mater. 2021, 31, 2007511. [Google Scholar] [CrossRef] [Scilit]
  266. Li, Y.; Jin, J.; Fan, W.; Huang, D. π-Extension of Indoles Using Acrolein Linker: Synthesis of Indolo[3,2-a]carbazole-6-carbaldehydes and Racemosin B. Org. Lett. 2023, 25, 8284–8289. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  267. Tu, L.; Wang, H.; Li, X.; Wang, X.; Li, M.; Wang, Y.; Shi, Y. Dithiene-Fused Quinoxalineimide-Based All-Acceptor Polymers for n-Type Organic Semiconductors. J. Mater. Chem. C 2023, 11, 11905–11911. [Google Scholar] [CrossRef] [Scilit]
  268. Gupta, V.; Pandeya, S.K.; Singh, R.P. Facile Synthesis of Triphenylenes and Triphenylene/Phenanthrene Fused Heteroaromatics. Org. Biomol. Chem. 2018, 16, 7134–7138. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  269. Jacob, L.; Gowda, A.; Kumar, S.; Belyaev, V. Synthesis, Thermal and Photophysical Studies of π–Extended Dibenzophenazine Based Discotic Liquid Crystals. J. Mol. Liq. 2020, 320, 114419. [Google Scholar] [CrossRef] [Scilit]
  270. Roß, L.; Reitemeier, J.; Ghalami, F.; Zhang, W.-S.; Gross, J.H.; Rominger, F.; Elbert, S.M.; Schröder, R.; Elstner, M.; Mastalerz, M. Two Dimensional Triptycene End-Capping and Its Influence on the Self-Assembly of Quinoxalinophenanthrophenazines. Chin. J. Chem. 2023, 41, 1198–1208. [Google Scholar] [CrossRef] [Scilit]
  271. Uçar, S.; Daştan, A. Transition Metal-Free Heteroarylation of Quinoxaline: Construction of Heteroaryl-Fused Phenazines by Oxidative Coupling. J. Org. Chem. 2020, 85, 15502–15513. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  272. Kvashnin, Y.A.; Verbitskiy, E.V.; Rusinov, G.L.; Charushin, V.N. Modification and application of 1,2,5-oxadiazolo[3,4-b]pyrazine derivatives: Highlights and perspectives. Russ. Chem. Bull. 2022, 71, 1342–1362. [Google Scholar] [CrossRef] [Scilit]
  273. Steparuk, A.S.; Kvashnin, Y.A.; Rusinov, G.L.; Verbitskiy, E.V.; Aleksandrov, A.E.; Lypenko, D.A.; Tameev, A.R.; Charushin, V.N. The first application of push-pull systems based on 1,2,5-oxadiazolo[3,4-b]pyrazine in organic light-emitting diodes and perovskite solar cells. Russ. Chem. Bull. 2023, 72, 527–533. [Google Scholar] [CrossRef] [Scilit]
  274. Kvashnin, Y.A.; Slepukhin, P.A.; Gazizov, D.A.; Zhilina, E.F.; Rusinov, G.L.; Verbitskiy, E.V.; Charushin, V.N. (E)-2-(6-(4′-(Diphenylamino)-[1,1′-biphenyl]-2-yl)-[1,2,5]oxadiazolo[3,4-b]pyrazin-5(4H)-ylidene)-2-(6-(4′-(diphenylamino)-[1,1′-biphenyl]-2-yl)-[1,2,5]oxadiazolo[3,4-b]pyrazin-5-yl)acetonitrile. Molbank 2023, 2023, M1714. [Google Scholar] [CrossRef] [Scilit]
  275. Krynina, E.M.; Kvashnin, Y.A.; Gazizov, D.A.; Kodess, M.I.; Ezhikova, M.A.; Rusinov, G.L.; Verbitskiy, E.V.; Charushin, V.N. Two-step synthesis of new fused systems based on [1,2,5]oxadiazolo[3,4-b]quinoxaline by a combination of the Scholl reaction and nucleophilic aromatic substitution of hydrogen (SNH). Russ. Chem. Bull. 2024, 73, 1647–1658. [Google Scholar] [CrossRef] [Scilit]
  276. Verbitskiy, E.V.; Kvashnin, Y.A.; Medvedeva, M.V.; Svalova, T.S.; Kozitsina, A.N.; Eltsov, O.S.; Rusinov, G.L.; Charushin, V.N. First synthesis of new polycyclic systems from ortho-di(heteroaryl)-substituted furazanopyrazine derivatives by the Scholl reaction. Mendeleev Commun. 2022, 32, 722–725. [Google Scholar] [CrossRef] [Scilit]
  277. Valvi, M.B.; Badhani, G.; More, K.P.; Adimurthy, S. Brønsted Acid-Mediated Mono- and Di-substitution of Quinoxalines with Indoles: A Pathway to Indolocarbazole-Quinoxaline Scaffolds. Chem. Commun. 2025, 61, 4698–4701. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  278. Li, J.; Zhu, Z.-Q. Donor-Acceptor Type Thermally Activated Delayed Fluorescent Materials Based on Imidazo[1,2-f]phenanthridine and Analogues. Patent US20180337345A1, 18 May 2018. [Google Scholar]
  279. Burešová, Z.; Grygarová, M.; Prokopová, E.; Klikar, M.; Pytela, O.; Váňa, J.; Fahim, A.M.M.; Jana, K.; Zubova, E.; Bartáček, J.; et al. Divergent Photoreduction of Nitroaromatic Compounds Catalysed by Dithienoquinoxaline. J. Catal. 2025, 445, 116033. [Google Scholar] [CrossRef] [Scilit]
  280. Keshtov, M.L.; Konstantinov, I.O.; Kuklin, S.A.; Davydova, N.K.; Alekseev, V.G.; Xie, Z.; Agrawald, A.; Sharma, G.D. New Wide-Bandgap D–A Polymer Based on Pyrrolo[3,4-b]dithieno[2,3-f:3′,2′-h]quinoxalindione and Thiazole Functionalized benzo[1,2-b:4,5-b′]dithiophene Units for High-Performance Ternary Organic Solar Cells with over 16% Efficiency. Sustain. Energy Fuels 2022, 6, 682–692. [Google Scholar] [CrossRef] [Scilit]
  281. Tsyganov, D.V.; Komogortsev, A.N.; Melekhina, V.G.; Fakhrutdinov, A.N.; Lichitsky, B.V. Photochemical Method for Preparation of Benzo[a]pyrano[3,2-c]phenazin-4-ones from Quinoxalines with 4-Pyranone Unit. J. Heterocycl. Chem. 2024, 61, 1387–1398. [Google Scholar] [CrossRef] [Scilit]
  282. Ucar, S.; Dastan, A. One-pot Homo- and Cross-coupling of Diazanaphthalenes via C-H Substitution: Synthesis of Bis- and Tris-diazanaphthalenes. J. Heterocycl. Chem. 2020, 57, 4013–4022. [Google Scholar] [CrossRef] [Scilit]
  283. Li, J. Thermally Assisted Delayed Fluorescent Materials with Triad-Type Materials. Patent US20180334459A1, 18 May 2018. [Google Scholar]
  284. Jang, J.; Kim, M.; Kim, K.; Lee, W. Compound and Organic Electronic Component Comprising the Same. Patent CN107619410A, 13 July 2017. [Google Scholar]
  285. Kvashnin, Y.A.; Verbitskiy, E.V.; Eltsov, O.S.; Slepukhin, P.A.; Tameev, A.R.; Nekrasova, N.V.; Rusinov, G.L.; Nunzi, J.-M.; Chupakhin, O.N.; Charushin, V.N. Dibenzo[f,h]furazano[3,4-b]quinoxalines: Synthesis by intramolecular cyclization through direct transition metal-free C–H functionalization and electrochemical, photophysical, and charge mobility characterization. ACS Omega 2020, 5, 8200–8210. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  286. Kvashnin, Y.A.; Krynina, E.M.; Medvedeva, M.V.; Svalova, T.S.; Kozitsina, A.N.; Eltsov, O.S.; Rusinov, G.L.; Verbitskiy, E.V.; Charushin, V.N. Synthesis of new polycyclic systems based on [1,2,5]chalcogenodiazolo[3,4-b]thieno[3,2-h]quinoxalines. Russ. Chem. Bull. 2023, 72, 939–947. [Google Scholar] [CrossRef] [Scilit]
  287. Verbitskiy, E.V.; Dinastiya, E.M.; Baranova, A.A.; Eltsov, O.S.; Rusinov, G.L.; Chupakhin, O.N.; Charushin, V.N. Synthesis of dithienoquinazolines from pyrimidines via intramolecular nucleophilic aromatic substitution of hydrogen. Chem. Heterocycl. Compd. 2017, 53, 1156–1160. [Google Scholar] [CrossRef] [Scilit]
  288. Verbitskiy, E.V.; Eltsov, O.S.; Zhilina, E.F.; Pakhomov, I.M.; Rusinov, G.L.; Chupakhin, O.N.; Charushin, V.N. New approach to unsymmetrical 1,3-diazatriphenylenes through intramolecular oxidative cyclodehydrogenation. Tetrahedron 2019, 75, 2687–2696. [Google Scholar] [CrossRef] [Scilit]
  289. Nishiyama, Y.; Akiyama, K.; Sakata, Y.; Hosoya, T.; Yoshida, S. Facile Synthesis of Tetraarylpyrazines by Sequential Cross-Coupling Approach. Chem. Lett. 2021, 50, 180–183. [Google Scholar] [CrossRef] [Scilit]
  290. Pashazadeh, R. Organic Molecules for Optoelectronic Devices. Patent WO2022069453A1, 28 September 2021. [Google Scholar]
  291. Gulevskaya, A.V.; Shvydkova, E.A.; Tonkoglazova, D.I. Synthesis and Characterization of Pyridine-, Pyrazine-, and Quinoxaline-Derived [4]Helicenes and S-Shaped Double [4]Helicenes. Eur. J. Org. Chem. 2018, 2018, 5030–5043. [Google Scholar] [CrossRef] [Scilit]
  292. Gulevskaya, A.V.; Tonkoglazova, D.I.; Guchunov, A.S.; Misharev, A.D. Synthesis and Characterization of Azine-[5]Helicene Hybrids. Eur. J. Org. Chem. 2019, 2018, 4879–4890. [Google Scholar] [CrossRef] [Scilit]
  293. Tonkoglazova, D.I.; Gulevskaya, A.V.; Chistyakov, K.A.; Askalepova, O.I. Synthesis, Crystal Structures and Properties of Carbazole-Based [6]Helicenes Fused with an Azine Ring. Beilstein J. Org. Chem. 2021, 17, 11–21. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  294. Tonkoglazova, D.I.; Oryabinskaya, L.M.; Shcherbatykh, A.A.; Gulevskaya, A.V. The Synthesis and Crystal Structure of pH-Sensitive Fluorescent Pyrene-Based Double Aza- and Diaza[4]helicenes. Org. Biomol. Chem. 2022, 20, 2704–2714. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  295. Otani, T.; Sasayama, T.; Horiuchi, M.; Okauchi, S.; Kawai, H.; Kitahara, M.; Imai, Y.; Shibata, T. Synthesis and Chiroptical Properties of Quinoxaline-Fused Polyaza[5]–[7]helicenes with Orange-Color CPL Emissions. Helv. Chim. Acta. 2021, 104, e2100016. [Google Scholar] [CrossRef] [Scilit]
  296. Yu, Z.; Shi, G.; Wang, K.-P.; Xu, L.-Z.; Chen, S.; Hu, Z.-Q. Benzothiadiazole-Derived Double Aza [5]helicenes: Synthesis, Crystal Structure and Optical Properties. Tetrahedron 2023, 130, 133178. [Google Scholar] [CrossRef] [Scilit]
  297. Kiel, G.R.; Samkian, A.E.; Nicolay, A.; Witzke, R.J.; Tilley, T.D. Titanocene-Mediated Dinitrile Coupling: A Divergent Route to Nitrogen-Containing Polycyclic Aromatic Hydrocarbons. J. Am. Chem. Soc. 2018, 140, 2450–2454. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  298. Ajay, C.; Chary, D.Y.; Balasubramanian, S.; Reddy, B.V.S. Rh(III)-Catalyzed Oxidative Annulation of 2-Arylquinoxalines with Cyclic 2-Diazo-1,3-diketones by C−H Bond Activation. Eur. J. Org. Chem. 2023, 26, e202201361. [Google Scholar] [CrossRef] [Scilit]
  299. Li, K.; Lin, H.-F.; Bi, H.-Y.; Shi, W.-M.; Ma, X.-P.; Mo, D.-L. Synthesis of Dibenzo[a,c]phenazines through Brønsted Acid-Catalyzed Skeletal Editing of 2-Arylindoles with 1,2-Diaminoarenes. Org. Lett. 2025, 27, 11596–11601. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  300. Verbitskiy, E.V.; Lipunova, G.N.; Nosova, E.V.; Charushin, V.N. Advances in the design of functionalized 1,4-diazines as components for photo- or/and electroactive materials. Dye. Pigment. 2023, 220, 111763. [Google Scholar] [CrossRef] [Scilit]
  301. Li, Y.; Fan, X.; Li, Y.; Liu, S.; Chuah, C.; Tang, Y.; Kwok, R.T.K.; Lam, J.W.Y.; Lu, X.; Qian, J.; et al. Molecular Crystal Engineering of Organic Chromophores for NIR-II Fluorescence Quantification of Cerebrovascular Function. ACS Nano 2022, 16, 3323–3331. [Google Scholar] [CrossRef] [Scilit] [PubMed]
  302. Li, Y.; Zha, M.; Kang, T.; Li, C.; Wu, X.; Wang, S.; Lu, S.-B.; Lee, Y.-S.; Wu, Y.-R.; Ni, J.-S.; et al. Promoted NIR-II Fluorescence by Heteroatom-Inserted Rigid-Planar Cores for Monitoring Cell Therapy of Acute Lung Injury. Small 2022, 18, 2105362. [Google Scholar] [CrossRef] [Scilit]
  303. Krynina, E.M.; Kvashnin, Y.A.; Zhilina, E.F.; Gazizov, D.A.; Slepukhin, P.A.; Rusinov, G.L.; Verbitskiy, E.V.; Charushin, V.N. [1,2,5]Oxadiazolo[3,4-b]dithieno[2,3-f:2′,3′-h]quinoxaline as a Versatile Scaffold for the Construction of Various Polycyclic Systems as Potential Organic Semiconductors. Chemistry 2025, 7, 158. [Google Scholar] [CrossRef] [Scilit]
  304. Kvashnin, Y.A.; Zhilina, E.F.; Dubovik, A.I.; Gazizov, D.A.; Mekhaev, A.V.; Krynina, E.M.; Rusinov, G.L.; Verbitskiy, E.V.; Charushin, V.N. Conversion of tetraphenylethylene-substituted oxadiazolo[3,4-b]pyrazines into the corresponding imidazo[4,5-b]- and pyrazino[2,3-b]pyrazines, as chemosensors for the selective detection of nitroaromatics in aqueous media. Dye. Pigment. 2024, 228, 112253. [Google Scholar] [CrossRef] [Scilit]
Molecules 31 02197 g001
Figure 1. Synthetic approaches to 1,4-diazatriphenylene derivatives and their heteroanalogs.
Figure 1. Synthetic approaches to 1,4-diazatriphenylene derivatives and their heteroanalogs.
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Molecules 31 02197 g002
Figure 2. Structures of various 1,4-diazatriphenylenes and their hetero-fused analogs, which are discussed in this review.
Figure 2. Structures of various 1,4-diazatriphenylenes and their hetero-fused analogs, which are discussed in this review.
Molecules 31 02197 g002
Molecules 31 02197 sch001
Scheme 1. Synthesis of dibenzo[a,c]phenazine (3a).
Scheme 1. Synthesis of dibenzo[a,c]phenazine (3a).
Molecules 31 02197 sch001
Molecules 31 02197 sch002
Scheme 2. Synthesis of dibenzo[a,c]phenazine (9), pyrazino[2,3-f][1,10]phenatroline (10), phenanthro[4,5-fgh]quinoxaline (11), dibenzo[f,h]quinoxaline (3, 18–21), pyrazino[2,3-f][1,10]phenatrolines (22–26), and phenanthro[4,5-fgh]quinoxalines (27, 28).
Scheme 2. Synthesis of dibenzo[a,c]phenazine (9), pyrazino[2,3-f][1,10]phenatroline (10), phenanthro[4,5-fgh]quinoxaline (11), dibenzo[f,h]quinoxaline (3, 18–21), pyrazino[2,3-f][1,10]phenatrolines (22–26), and phenanthro[4,5-fgh]quinoxalines (27, 28).
Molecules 31 02197 sch002
Molecules 31 02197 sch003
Scheme 3. Synthesis of [7]helicenes (29a–g).
Scheme 3. Synthesis of [7]helicenes (29a–g).
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Molecules 31 02197 sch004
Scheme 4. Synthesis of 1,4-diazatriphenylene derivatives 9n, 3db, and 3dc.
Scheme 4. Synthesis of 1,4-diazatriphenylene derivatives 9n, 3db, and 3dc.
Molecules 31 02197 sch004
Molecules 31 02197 sch005
Scheme 5. Synthesis of quinoxalino[2′,3′,9,10]phenanthro[4,5-abc]phenanzine (36).
Scheme 5. Synthesis of quinoxalino[2′,3′,9,10]phenanthro[4,5-abc]phenanzine (36).
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Molecules 31 02197 sch006
Scheme 6. Synthesis of symmetrical (45a–f) and unsymmetrical heteroanalogs of 1,4-diazatriphenylene (45g–k).
Scheme 6. Synthesis of symmetrical (45a–f) and unsymmetrical heteroanalogs of 1,4-diazatriphenylene (45g–k).
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Molecules 31 02197 sch007
Scheme 7. Synthesis of fused systems based on the [1,2,5]oxadiazolo[3,4-b]quinoxaline core (51a–c and 52a–c).
Scheme 7. Synthesis of fused systems based on the [1,2,5]oxadiazolo[3,4-b]quinoxaline core (51a–c and 52a–c).
Molecules 31 02197 sch007
Molecules 31 02197 sch008
Scheme 8. Synthesis of asymmetrical derivatives of [1,2,5]oxadiazolo-fused heteroanalogs of 1,4-diazatriphenylene (56–58).
Scheme 8. Synthesis of asymmetrical derivatives of [1,2,5]oxadiazolo-fused heteroanalogs of 1,4-diazatriphenylene (56–58).
Molecules 31 02197 sch008
Molecules 31 02197 sch009
Scheme 9. Synthesis of 5,6-dihydrodiindolo[3,2-a:2′,3′-c]phenazine derivatives (61a–d).
Scheme 9. Synthesis of 5,6-dihydrodiindolo[3,2-a:2′,3′-c]phenazine derivatives (61a–d).
Molecules 31 02197 sch009
Molecules 31 02197 sch010
Scheme 10. Synthesis of 1,4-diazatriphenylene derivatives (66a–d).
Scheme 10. Synthesis of 1,4-diazatriphenylene derivatives (66a–d).
Molecules 31 02197 sch010
Molecules 31 02197 sch011
Scheme 11. Synthesis of dithieno[2,3-f:3′,2′-h]quinoxalines (68a,b).
Scheme 11. Synthesis of dithieno[2,3-f:3′,2′-h]quinoxalines (68a,b).
Molecules 31 02197 sch011
Molecules 31 02197 sch012
Scheme 12. Synthesis of dithieno[2,3-f:3′,2′-h]quinoxaline derivative (70).
Scheme 12. Synthesis of dithieno[2,3-f:3′,2′-h]quinoxaline derivative (70).
Molecules 31 02197 sch012
Molecules 31 02197 sch013
Scheme 13. Synthesis of dithieno[3,2-f:2′,3′-h]quinoxaline derivatives (74–76).
Scheme 13. Synthesis of dithieno[3,2-f:2′,3′-h]quinoxaline derivatives (74–76).
Molecules 31 02197 sch013
Molecules 31 02197 sch014
Scheme 14. Synthesis of 4H-benzo[a]pyrano[3,2-c]phenazin-4-ones (78a–g) and 4H-pyrano[2,3-a]thieno[3,2-c]phenazin-4-one (78h) derivatives.
Scheme 14. Synthesis of 4H-benzo[a]pyrano[3,2-c]phenazin-4-ones (78a–g) and 4H-pyrano[2,3-a]thieno[3,2-c]phenazin-4-one (78h) derivatives.
Molecules 31 02197 sch014
Molecules 31 02197 sch015
Scheme 15. Synthesis of diquinoxalino[2,3-a:2′,3′-c]phenazine (80).
Scheme 15. Synthesis of diquinoxalino[2,3-a:2′,3′-c]phenazine (80).
Molecules 31 02197 sch015
Molecules 31 02197 sch016
Scheme 16. Synthesis of substituted indolo[2,1-a]pyrazino[2,3-c]isoquinolines (82a,b).
Scheme 16. Synthesis of substituted indolo[2,1-a]pyrazino[2,3-c]isoquinolines (82a,b).
Molecules 31 02197 sch016
Molecules 31 02197 sch017
Scheme 17. Synthesis of 13,14-dihydroindolo[2,3-a]pyrazino[2,3-c]carbazole (86).
Scheme 17. Synthesis of 13,14-dihydroindolo[2,3-a]pyrazino[2,3-c]carbazole (86).
Molecules 31 02197 sch017
Molecules 31 02197 sch018
Scheme 18. Synthesis of dibenzo[f,h][1,2,5]oxadiazolo[3,4-b]quinoxalines (91a–g).
Scheme 18. Synthesis of dibenzo[f,h][1,2,5]oxadiazolo[3,4-b]quinoxalines (91a–g).
Molecules 31 02197 sch018
Molecules 31 02197 sch019
Scheme 19. Synthesis of benzo[f][1,2,5]chalcogenodiazolo[3,4-b]thieno[3,2-h]quinoxalines and their benzo-fused derivatives (93a–f).
Scheme 19. Synthesis of benzo[f][1,2,5]chalcogenodiazolo[3,4-b]thieno[3,2-h]quinoxalines and their benzo-fused derivatives (93a–f).
Molecules 31 02197 sch019
Molecules 31 02197 sch020
Scheme 20. Synthesis of 2-(4-methoxyphenyl)-7-methyl-3-(4-(trifluoromethyl)phenyl)dibenzo[f,h]quinoxaline (98).
Scheme 20. Synthesis of 2-(4-methoxyphenyl)-7-methyl-3-(4-(trifluoromethyl)phenyl)dibenzo[f,h]quinoxaline (98).
Molecules 31 02197 sch020
Molecules 31 02197 sch021
Scheme 21. Synthesis of polycyclic systems 102a–c.
Scheme 21. Synthesis of polycyclic systems 102a–c.
Molecules 31 02197 sch021
Molecules 31 02197 sch022
Scheme 22. Synthesis of benzo[f]naphtho[1,2-h]quinoxaline derivatives (110a–k).
Scheme 22. Synthesis of benzo[f]naphtho[1,2-h]quinoxaline derivatives (110a–k).
Molecules 31 02197 sch022
Molecules 31 02197 sch023
Scheme 23. Synthesis of polyaza[5]helicene (116) and polyaza[7]helicene (117).
Scheme 23. Synthesis of polyaza[5]helicene (116) and polyaza[7]helicene (117).
Molecules 31 02197 sch023
Molecules 31 02197 sch024
Scheme 24. Synthesis of 7,10-di-tert-butyl-18,19-diphenyldinaphtho[2,1-c:1′,2′-i]pyrazino[2,3-f][1,10]phenanthroline (119).
Scheme 24. Synthesis of 7,10-di-tert-butyl-18,19-diphenyldinaphtho[2,1-c:1′,2′-i]pyrazino[2,3-f][1,10]phenanthroline (119).
Molecules 31 02197 sch024
Molecules 31 02197 sch025
Scheme 25. Synthesis of 2,3,7,10-tetra-substituted dibenzo[f,h]quinoxalines (123a–f).
Scheme 25. Synthesis of 2,3,7,10-tetra-substituted dibenzo[f,h]quinoxalines (123a–f).
Molecules 31 02197 sch025
Molecules 31 02197 sch026
Scheme 26. Synthesis of 2,3-dihydrodibenzo[a,c]phenazin-4(1H)-one derivatives (126a–u).
Scheme 26. Synthesis of 2,3-dihydrodibenzo[a,c]phenazin-4(1H)-one derivatives (126a–u).
Molecules 31 02197 sch026
Molecules 31 02197 sch027
Scheme 27. Synthesis of substituted dibenzo[a,c]phenazines (3a-wd).
Scheme 27. Synthesis of substituted dibenzo[a,c]phenazines (3a-wd).
Molecules 31 02197 sch027
Molecules 31 02197 g003
Figure 3. Selected examples of compounds (3ac, 21a, 25b, 26, and 27j) that are promising for utilization in organic field-effect transistors, OLEDs, and solar cells.
Figure 3. Selected examples of compounds (3ac, 21a, 25b, 26, and 27j) that are promising for utilization in organic field-effect transistors, OLEDs, and solar cells.
Molecules 31 02197 g003
Molecules 31 02197 g004
Figure 4. Examples of narrow-gap n-type semiconductors based on 1,4-diazatriphenylene and its hetero-fused analogs (27h, 27i, 56a,b, 58a,b, and 128a,b).
Figure 4. Examples of narrow-gap n-type semiconductors based on 1,4-diazatriphenylene and its hetero-fused analogs (27h, 27i, 56a,b, 58a,b, and 128a,b).
Molecules 31 02197 g004
Molecules 31 02197 g005
Figure 5. Examples of polycyclic compounds (3ab, 22a, 22h, 22k, 22ac, and 22ag) utilized as electrochromic materials and components for electrodes in metal-ion batteries.
Figure 5. Examples of polycyclic compounds (3ab, 22a, 22h, 22k, 22ac, and 22ag) utilized as electrochromic materials and components for electrodes in metal-ion batteries.
Molecules 31 02197 g005
Molecules 31 02197 g006
Figure 6. Examples of polycyclic compounds utilized as sensors for detecting nitro-explosives (compound 135) and metal cations (compounds 80, 136–139).
Figure 6. Examples of polycyclic compounds utilized as sensors for detecting nitro-explosives (compound 135) and metal cations (compounds 80, 136–139).
Molecules 31 02197 g006
Molecules 31 02197 g007
Figure 7. Examples of polycyclic compounds utilized as photocatalysts for various chemical reactions (compounds 3t, 9d, 9g, 10c, 22ak, and 22al).
Figure 7. Examples of polycyclic compounds utilized as photocatalysts for various chemical reactions (compounds 3t, 9d, 9g, 10c, 22ak, and 22al).
Molecules 31 02197 g007
Molecules 31 02197 g008
Figure 8. Examples of polycyclic ligands (10d, 22a, 22d, 22j, 22u, 22x, 22ab, 22ad, and 22ae) used for the synthesis of biologically active metal complexes.
Figure 8. Examples of polycyclic ligands (10d, 22a, 22d, 22j, 22u, 22x, 22ab, 22ad, and 22ae) used for the synthesis of biologically active metal complexes.
Molecules 31 02197 g008
Molecules 31 02197 g009
Figure 9. Examples of polycyclic compounds (140 and 141) utilized as fluorophores for in vivo bioimaging in the second near-infrared window.
Figure 9. Examples of polycyclic compounds (140 and 141) utilized as fluorophores for in vivo bioimaging in the second near-infrared window.
Molecules 31 02197 g009
Table 1. Selected examples of the preparation of derivatives of dibenzo[a,c]phenazine (9), pyrazino[2,3-f][1,10]phenatroline (10), and phenanthro[4,5-fgh]quinoxaline (11).
Table 1. Selected examples of the preparation of derivatives of dibenzo[a,c]phenazine (9), pyrazino[2,3-f][1,10]phenatroline (10), and phenanthro[4,5-fgh]quinoxaline (11).
Entry1,2-Diketones
(4–6)		1,2-Diamines
(7 or 8)		ConditionsProducts (9–11)
—Isolated Yield		Ref.
1Molecules 31 02197 i001Molecules 31 02197 i002Fe3O4@EDA-SO3H, MNR catalyst, rt, 15 min/EtOH
Molecules 31 02197 i003		Molecules 31 02197 i004[12]
2Molecules 31 02197 i005Molecules 31 02197 i006reflux, 12 h/AcOHMolecules 31 02197 i007[13]
3Molecules 31 02197 i008Molecules 31 02197 i00940 °C, 8 h/solvent-freeMolecules 31 02197 i010[14]
4Molecules 31 02197 i011Molecules 31 02197 i012reflux, 12 h/AcOHMolecules 31 02197 i013[13]
5Molecules 31 02197 i014Molecules 31 02197 i015reflux, 12 h/AcOHMolecules 31 02197 i016[15]
6Molecules 31 02197 i017nano-Ca(IO3)2, rt, 9 min/AcOHMolecules 31 02197 i018[16]
7Molecules 31 02197 i019Molecules 31 02197 i020110 °C, 2 h/AcOHMolecules 31 02197 i021[17]
8Molecules 31 02197 i022Molecules 31 02197 i02336% HCl, 40 °C, 48 h/EtOH–THF (1:1)Molecules 31 02197 i024[18]
9Molecules 31 02197 i025Molecules 31 02197 i026reflux, 6 h/AcOHMolecules 31 02197 i027[19]
10Molecules 31 02197 i028Molecules 31 02197 i02936% HCl, 40 °C, 48 h/EtOH–THF (1:1)Molecules 31 02197 i030[18]
11Molecules 31 02197 i031Molecules 31 02197 i0321. TsOH (cat.), reflux, 5 h/EtOH
2. reflux, 12 h/AcOH		Molecules 31 02197 i033[15,20]
12Molecules 31 02197 i034Molecules 31 02197 i03560 °C, 24 h/AcOHMolecules 31 02197 i036[21]
13Molecules 31 02197 i037Molecules 31 02197 i0381. TsOH (cat.), reflux, 5 h/EtOH
2. reflux, 12 h/AcOH
3. reflux, 3 h/AcOH		Molecules 31 02197 i039[15,20,22]
14Molecules 31 02197 i040Molecules 31 02197 i041125 °C, 12 h/AcOHMolecules 31 02197 i042[23]
15Molecules 31 02197 i043Molecules 31 02197 i04460 °C, 12 h/H2OMolecules 31 02197 i045[24,25]
16Molecules 31 02197 i046Molecules 31 02197 i047reflux, 4 h/THFMolecules 31 02197 i048[26]
17Molecules 31 02197 i049Molecules 31 02197 i050TsOH (cat.), reflux, 16 h/EtOHMolecules 31 02197 i051[27]
18Molecules 31 02197 i052Molecules 31 02197 i053reflux, 4 h/EtOHMolecules 31 02197 i054[28]
19Molecules 31 02197 i055Molecules 31 02197 i056For R = H:
1. reflux, 12 h/AcOH
2. 120 °C, 12 h/AcOH
For R = t-Bu:
120 °C, 20 h/AcOH		Molecules 31 02197 i057[29,30,31]
20Molecules 31 02197 i058Molecules 31 02197 i059reflux, 12 h/AcOHMolecules 31 02197 i060[29]
21Molecules 31 02197 i061Molecules 31 02197 i062reflux, 12 h/AcOHMolecules 31 02197 i063[29]
22Molecules 31 02197 i064Molecules 31 02197 i065reflux, 12 h/AcOHMolecules 31 02197 i066[29]
23Molecules 31 02197 i067Molecules 31 02197 i068reflux, 12 h/AcOH–EtOH (1:1)Molecules 31 02197 i069[32]
24Molecules 31 02197 i070Molecules 31 02197 i0711. reflux, 24 h/AcOH
2. 80 °C, 19 h/AcOH–EtOH (1:1)		Molecules 31 02197 i072[33,34]
25Molecules 31 02197 i073Molecules 31 02197 i074reflux, 8 h/AcOHMolecules 31 02197 i075[35]
26Molecules 31 02197 i076Molecules 31 02197 i07780 °C, 15 h/AcOH–EtOH (1:1)Molecules 31 02197 i078[36]
27Molecules 31 02197 i079Molecules 31 02197 i080reflux, 8 h/AcOHMolecules 31 02197 i081[35]
28Molecules 31 02197 i082Molecules 31 02197 i083reflux, 24 h/AcOHMolecules 31 02197 i084[33]
Table 2. Synthesis of 1,4-diazatriphenylene derivatives (3 and 18–21), pyrazino[2,3-f][1,10]phenatrolines (22–26), and phenanthro[4,5-fgh]quinoxalines (27, 28).
Table 2. Synthesis of 1,4-diazatriphenylene derivatives (3 and 18–21), pyrazino[2,3-f][1,10]phenatrolines (22–26), and phenanthro[4,5-fgh]quinoxalines (27, 28).
Entry1,2-Diketones
(4–6)		1,2-Diamines
(12–17)		ConditionsProducts (3, 18–28)
—Isolated Yield		Ref.
1Molecules 31 02197 i085Molecules 31 02197 i0861. nano-γ-Fe2O3-SO3H, 120 °C, 1 h/solvent-free
2. Fe3O4@APTES@isatin-SO3H, MNR catalyst, rt, 20 min/EtOH
Molecules 31 02197 i087
3. Ionic liquid [BBSA-DBN][HSO4] (3 mol%), 80 °C, 35 min/EtOH
Molecules 31 02197 i088
4. amorphous Fe nanoparticles, rt, 7 min/H2O
5. SiO2/[SEP]Cl, 65 °C, 2 h/EtOH
Molecules 31 02197 i089
6. HOOCCH2C(=CH2)COOH, rt, 1 h/H2O
7. CSA (20 mol%), rt, 1 h/EtOH–H2O (1:1)
Molecules 31 02197 i090
8. MW, 20–22 bar, 230 °C, 10 min/5% AcOH
9. nano-Ca(IO3)2, rt, 3 min/AcOH
10. mesoporous TG-PSSA-co-ACA, rt, 5 min/H2O
Molecules 31 02197 i091
11. Fe3O4@EDA-SO3H, MNR catalyst, rt, immediately/EtOH
12. reflux, 24 h/EtOH
13. [DABCO](SO3H)2CoCl4, reflux, 18 min/H2O
Molecules 31 02197 i092		Molecules 31 02197 i093[12,16,37,38,39,40,41,42,43,44,45,46,47]
2Molecules 31 02197 i094Molecules 31 02197 i0951. reflux, 8 h/AcOH
2. 110 °C, 12 h/AcOH		Molecules 31 02197 i096[48,49]
3Molecules 31 02197 i097reflux, 2 h/AcOH–EtOH
(1:1)		Molecules 31 02197 i098[50]
4Molecules 31 02197 i099CSA (20 mol%), rt, 1 h/EtOH–H2O (1:1)Molecules 31 02197 i100[43]
5Molecules 31 02197 i10175 °C, 18 h/EtOH–CH2Cl2
(5:1)		Molecules 31 02197 i102[51]
6Molecules 31 02197 i103HOOCCH2C(=CH2)COOH, rt, 1 h/H2OMolecules 31 02197 i104[42]
7Molecules 31 02197 i1051. reflux, 8 h/AcOH
2. reflux, 8 h/AcOH
3. SiO2/[SEP]Cl, 65 °C, 1 h 45 min/EtOH
4. 110 °C, 12 h/AcOH
5. Zn(OAc)2 (cat.), 170 °C, 12 h/quinoline		Molecules 31 02197 i106[41,48,49,52,53]
8Molecules 31 02197 i1071. Fe3O4@APTES@isatin-SO3H, MNR catalyst, rt, 20 min/EtOH
2. ionic liquid [BBSA-DBN][HSO4] (3 mol%), 80 °C, 30 min/EtOH
3. SiO2/[SEP]Cl, 65 °C, 2 min/EtOH
4. HOOCCH2C(=CH2)COOH, rt, 1 h/H2O
5. [DABCO](SO3H)2CoCl4 (20 mg), reflux, 30 min/H2O		Molecules 31 02197 i108[38,39,41,42,47]
9Molecules 31 02197 i109HOOCCH2C(=CH2)COOH, rt, 1 h/H2OMolecules 31 02197 i110[42]
10Molecules 31 02197 i1111. Fe3O4@APTES@isatin-SO3H, MNR catalyst, rt, 17 min/EtOH
2. ionic liquid [BBSA-DBN][HSO4] (3 mol%), 80 °C, 35 min/EtOH
3. HOOCCH2C(=CH2)COOH, rt, 1 h/H2O
4. mesoporous TG-PSSA-co-ACA, rt, 5 min/H2O
5. [DABCO](SO3H)2CoCl4 (20 mg), reflux, 30 min/H2O		Molecules 31 02197 i112[38,39,41,42,47]
11Molecules 31 02197 i113Molecules 31 02197 i114Oc = C8H1775 °C, 16 h/EtOHMolecules 31 02197 i115[54]
12Molecules 31 02197 i11675 °C, 18 h/EtOH–CH2Cl2
(5:1)		Molecules 31 02197 i117[51]
13Molecules 31 02197 i118MW, 230 °C, 10 min/5% AcOHMolecules 31 02197 i119[55]
14Molecules 31 02197 i1201. SiO2/[SEP]Cl, 65 °C, 15 min/EtOH
2. mesoporous TG-PSSA-co-ACA, rt, 5 min/H2O
3. 120 °C, 8 h/AcOH		Molecules 31 02197 i121[41,45,56]
15Molecules 31 02197 i122reflux, 12 h/n-BuOHMolecules 31 02197 i123[57]
16Molecules 31 02197 i124reflux, 12 h/AcOHMolecules 31 02197 i125[49,58,59]
17Molecules 31 02197 i126120 °C, 8 h/AcOHMolecules 31 02197 i127[60]
18Molecules 31 02197 i128reflux, 12 h/n-BuOHMolecules 31 02197 i129[61]
19Molecules 31 02197 i1301. 80 °C, 4 h/AcOH–EtOH
2. reflux, 24 h/AcOH		Molecules 31 02197 i131[62,63]
20Molecules 31 02197 i132reflux, 8 h/AcOHMolecules 31 02197 i133[64]
21Molecules 31 02197 i134AcOH (cat.), reflux, 48 h/EtOHMolecules 31 02197 i135[65]
22Molecules 31 02197 i136Molecules 31 02197 i137125 °C, 12 h/AcOHMolecules 31 02197 i138[66]
23Molecules 31 02197 i139reflux, 12 h/AcOHMolecules 31 02197 i140[59]
24Molecules 31 02197 i1411. R = F: 125 °C, 12 h/AcOH
2. R = Br: reflux, 12 h/AcOH		Molecules 31 02197 i142[59,67]
25Molecules 31 02197 i143NEt3, reflux, 6 h/AcOH–EtOH (3:1)Molecules 31 02197 i144[46]
26Molecules 31 02197 i145reflux, 6 h/AcOH–EtOH (3:1)Molecules 31 02197 i146[68,69]
27Molecules 31 02197 i1471. amorphous Fe nanoparticles, rt, 7 min/H2O
2. CSA (20 mol%), rt, 1 h 30 min/EtOH–H2O (1:1)
3. nano-Ca(IO)3, rt, 9 min/AcOH
4. reflux, 24 h/i-PrOH		Molecules 31 02197 i148[16,40,43,70]
28Molecules 31 02197 i1491. amorphous Fe nanoparticles, rt, 10 min/H2O
2. reflux, 8 h/n-BuOH		Molecules 31 02197 i150[40,71]
29Molecules 31 02197 i151reflux, 12 h/n-BuOHMolecules 31 02197 i152[57]
30Molecules 31 02197 i153SiO2/[SEP]Cl, 65 °C, 15 min/EtOHMolecules 31 02197 i154[41]
31Molecules 31 02197 i155110 °C, 5 h/DMFMolecules 31 02197 i156[72]
32Molecules 31 02197 i157reflux, 6 h/AcOH–EtOH (1:2)Molecules 31 02197 i158[73]
33Molecules 31 02197 i159Molecules 31 02197 i160120 °C, 8 h/AcOHMolecules 31 02197 i161[74]
34Molecules 31 02197 i162reflux, 12 h/AcOH–EtOH (1:1)Molecules 31 02197 i163[75]
35Molecules 31 02197 i16480 °C, 24 h/AcOH–CHCl3
(1:1)		Molecules 31 02197 i165[76]
36Molecules 31 02197 i166Oc = C8H17
Un = C11H23		100 °C, 12 h/AcOH–EtOH (1:1)Molecules 31 02197 i167[77]
37Molecules 31 02197 i168Molecules 31 02197 i169reflux, 2 h/AcOHMolecules 31 02197 i170[78]
38Molecules 31 02197 i171reflux, 12 h/AcOHMolecules 31 02197 i172[79,80]
39Molecules 31 02197 i173Molecules 31 02197 i174reflux, 24 h/AcOHMolecules 31 02197 i175[81]
40Molecules 31 02197 i176Molecules 31 02197 i177reflux, 24 h/AcOHMolecules 31 02197 i178[81]
41Molecules 31 02197 i179Molecules 31 02197 i1801. R1 = R2 = R3 = H, 36% HCl, 40 °C, 48 h/EtOH–THF
(1:1)
2. R1 = R2 = Br, R3 = H, HCl (cat.), rt, 12 h/EtOH–THF
(1:1)
3. R1 = R2 = R3 = Br, HCl (cat.), rt, 12 h/EtOH–THF
(1:1)		Molecules 31 02197 i181[18]
42Molecules 31 02197 i182Molecules 31 02197 i18336% HCl, 40 °C, 48 h/EtOH–THF (1:1)Molecules 31 02197 i184[18]
43Molecules 31 02197 i185Molecules 31 02197 i186reflux, 12 h/n-BuOHMolecules 31 02197 i187[82]
44Molecules 31 02197 i188Molecules 31 02197 i189reflux, 12 h/n-BuOHMolecules 31 02197 i190[82]
45Molecules 31 02197 i191Molecules 31 02197 i192reflux, 12 h/n-BuOHMolecules 31 02197 i193[83]
46Molecules 31 02197 i194reflux, 8 h/AcOHMolecules 31 02197 i195[84]
47Molecules 31 02197 i196reflux, 12 h/n-BuOHMolecules 31 02197 i197[83]
48Molecules 31 02197 i198Molecules 31 02197 i1991. R = H, TsOH (cat.), reflux, 5 h/EtOH
2. R = H, 130 °C, 4 h/AcOH
3. R = Br, 130 °C, 4 h/AcOH		Molecules 31 02197 i200[85,86]
49Molecules 31 02197 i201reflux, 6 h/AcOH–EtOHMolecules 31 02197 i202[87]
50Molecules 31 02197 i203125 °C, 12 h/AcOHMolecules 31 02197 i204[66]
51Molecules 31 02197 i205Molecules 31 02197 i206AcOH (cat.), reflux, 1.5 h/EtOHMolecules 31 02197 i207[88]
52Molecules 31 02197 i208AcOH (cat.), reflux, 5 h/EtOHMolecules 31 02197 i209[89]
53Molecules 31 02197 i210reflux, 6 h/AcOH–EtOH (1:2)Molecules 31 02197 i211[73]
54Molecules 31 02197 i212reflux, 24 h/AcOHMolecules 31 02197 i213[90]
55
Molecules 31 02197 i214





Molecules 31 02197 i215		Molecules 31 02197 i2161. reflux, 2 h/AcOH
2. 80 °C, 4 h/AcOH–EtOH
3. reflux, 8 h/AcOH
4. TsOH (cat.), reflux, 2 h/AcOH		Molecules 31 02197 i217[62,78,91,92]
56Molecules 31 02197 i2181. reflux, 3 h/AcOH
2. 110 °C, 6 h/AcOH		Molecules 31 02197 i219[93,94,95]
57Molecules 31 02197 i220110 °C, 24 h/AcOHMolecules 31 02197 i221[96]
58Molecules 31 02197 i2221. reflux, 8 h/AcOH
2. reflux, 3 h/AcOH		Molecules 31 02197 i223[97,98]
59Molecules 31 02197 i2241. 80 °C, 2 h/EtOH
2. reflux, 12 h/AcOH		Molecules 31 02197 i225[99,100,101]
60










Molecules 31 02197 i226















Molecules 31 02197 i227		Molecules 31 02197 i2281. reflux, 3 h/AcOH
2. reflux, 6 h/AcOH
3. reflux, 8 h/AcOH
4. reflux, 10 h/EtOH		Molecules 31 02197 i229[91,93,94,102]
61Molecules 31 02197 i230reflux, 8 h/AcOHMolecules 31 02197 i231[91,103]
62Molecules 31 02197 i232125 °C, 24 h/AcOHMolecules 31 02197 i233[104]
63Molecules 31 02197 i2341. R1 = Br, R2 = H: reflux, 6 h/EtOH
2. R1 = H, R2 = Br: AcOH (cat.), reflux, 1 h 30 min/EtOH
3. R1 = H, R2 = Br: reflux, 6 h/EtOH		Molecules 31 02197 i235[88,105,106]
64Molecules 31 02197 i236AcOH (cat.), reflux, 5 h/EtOHMolecules 31 02197 i237[89]
65Molecules 31 02197 i238reflux, 24 h/AcOHMolecules 31 02197 i239[81]
66Molecules 31 02197 i240reflux, 24 h/AcOHMolecules 31 02197 i241[81]
67Molecules 31 02197 i242reflux, 6 h/AcOH–EtOH (1:2)Molecules 31 02197 i243[73]
68Molecules 31 02197 i244Molecules 31 02197 i245reflux, 12 h/AcOHMolecules 31 02197 i246[58]
69Molecules 31 02197 i247Molecules 31 02197 i24835 °C, 10 h/AcOH–EtOH
(1:3)		Molecules 31 02197 i249[107]
70Molecules 31 02197 i250Molecules 31 02197 i25190 °C, 24 h/AcOH–EtOH
(1:3)		Molecules 31 02197 i252[108]
71Molecules 31 02197 i253Molecules 31 02197 i25490 °C, 24 h/AcOH–EtOH
(1:3)		Molecules 31 02197 i255[108]
72Molecules 31 02197 i256Molecules 31 02197 i257reflux, 24 h/AcOHMolecules 31 02197 i258[81]
73Molecules 31 02197 i259reflux, 24 h/AcOHMolecules 31 02197 i260[81]
74Molecules 31 02197 i261Molecules 31 02197 i262reflux, 14 h/n-BuOHMolecules 31 02197 i263[61]
75Molecules 31 02197 i264Molecules 31 02197 i265140 °C, 14 h/n-BuOHMolecules 31 02197 i266[109]
76Molecules 31 02197 i267Molecules 31 02197 i268reflux, 14 h/n-BuOHMolecules 31 02197 i269[61]
77Molecules 31 02197 i270Molecules 31 02197 i271140 °C, 24 h/n-BuOHMolecules 31 02197 i272[109,110]
78Molecules 31 02197 i273Molecules 31 02197 i274AcOH (cat.), reflux, 24 h/EtOHMolecules 31 02197 i275[111]
79Molecules 31 02197 i276AcOH (cat.), reflux, 24 h/EtOHMolecules 31 02197 i277[111]
80Molecules 31 02197 i278Molecules 31 02197 i279AcOH (cat.), reflux, 24 h/EtOHMolecules 31 02197 i280[111]
81Molecules 31 02197 i281AcOH (cat.), reflux, 24 h/EtOHMolecules 31 02197 i282[111]
82Molecules 31 02197 i283AcOH (cat.), reflux, 24 h/EtOHMolecules 31 02197 i284[111]
83Molecules 31 02197 i285Molecules 31 02197 i286100 °C, 8 h/AcOHMolecules 31 02197 i287[112]
84Molecules 31 02197 i288reflux, 12 h/n-BuOHMolecules 31 02197 i289[113]
85Molecules 31 02197 i290100 °C, 8 h/AcOHMolecules 31 02197 i291[112]
86Molecules 31 02197 i292reflux, 12 h/n-BuOHMolecules 31 02197 i293[113]
87Molecules 31 02197 i294Molecules 31 02197 i295105 °C, 8 h/t-BuOHMolecules 31 02197 i296[114]
88Molecules 31 02197 i297Molecules 31 02197 i298130 °C, 4 h/AcOHMolecules 31 02197 i299[115]
89Molecules 31 02197 i300
Oc = C8H17
De = C10H21		Molecules 31 02197 i301reflux, 3 h/AcOH–tolueneMolecules 31 02197 i302[116]
90Molecules 31 02197 i303Molecules 31 02197 i304AcOH (cat.), reflux, 16 h/EtOHMolecules 31 02197 i305[117]
91Molecules 31 02197 i306Molecules 31 02197 i307NaOAc, reflux, 12 h/EtOHMolecules 31 02197 i308[118]
92Molecules 31 02197 i309Molecules 31 02197 i310reflux, 72 h/AcOH–EtOH (1:5)Molecules 31 02197 i311[119]
93Molecules 31 02197 i312Molecules 31 02197 i313reflux, 63 h/EtOHMolecules 31 02197 i314[120]
94Molecules 31 02197 i315Molecules 31 02197 i316reflux, 24 h/AcOHMolecules 31 02197 i317[121]
95Molecules 31 02197 i318reflux, 24 h/AcOHMolecules 31 02197 i319[121]
96Molecules 31 02197 i320

























Molecules 31 02197 i321








































Molecules 31 02197 i322		Molecules 31 02197 i3231. reflux, 3 h/EtOH
2. rt, 3 h/MeOH
3. 50 °C, 5 h/EtOH
4. reflux, 4 h/DMF
5. reflux, 10 h/MeOH
6. reflux, 8 h/EtOH		Molecules 31 02197 i324[122,123,124,125,126,127,128]
97Molecules 31 02197 i325reflux, 4 h/EtOHMolecules 31 02197 i326[129,130]
98Molecules 31 02197 i3271. reflux, 3 h/EtOH
2. reflux, 4 h/EtOH		Molecules 31 02197 i328[130,131]
99Molecules 31 02197 i3291. reflux, 4 h/EtOH
2. rt, 3 h/MeOH
3. reflux, 4 h/AcOH		Molecules 31 02197 i330[122,123,124,132,133]
100Molecules 31 02197 i3311. rt, 3 h/MeOH
2. reflux, 6 h/EtOH		Molecules 31 02197 i332[124,134]
101Molecules 31 02197 i3331. rt, 2 h/CH2Cl2
2. reflux, 4 h/EtOH
3. reflux, 8 h/EtOH		Molecules 31 02197 i334[128,135,136,137]
102Molecules 31 02197 i3351. reflux, 4 h/EtOAc–MeOH (7:1)
2. reflux, 4 h/EtOH
3. reflux, 8 h/EtOH		Molecules 31 02197 i336[28,128,138,139]
103Molecules 31 02197 i3371. reflux, 4 h/AcOH
2. reflux, 6 h/MeOH
3. reflux, 10 h/MeOH
4. reflux, 24 h/AcOH–EtOH (1:1)		Molecules 31 02197 i338[127,133,140,141]
104Molecules 31 02197 i339reflux, 4 h/AcOHMolecules 31 02197 i340[137,142]
105Molecules 31 02197 i3411. reflux, 4 h/EtOH
2. rt, 3 h/MeOH		Molecules 31 02197 i342[122,123,124,143]
106Molecules 31 02197 i3431. reflux, 4 h/EtOH
2. reflux, 10 h/MeOH
3. reflux, 8 h/EtOH		Molecules 31 02197 i344[127,128,139]
107Molecules 31 02197 i3451. reflux, 4 h/AcOH
2. reflux, 24 h/EtOH		Molecules 31 02197 i346[144,145]
108Molecules 31 02197 i347reflux, 2 h/AcOHMolecules 31 02197 i348[146]
109Molecules 31 02197 i349AcOH (cat.), 100 °C, 12 h/EtOHMolecules 31 02197 i350[147]
110Molecules 31 02197 i351reflux, 15 h/EtOHMolecules 31 02197 i352[148]
111Molecules 31 02197 i353reflux, 12 h/n-BuOHMolecules 31 02197 i354[57]
112Molecules 31 02197 i355Et3N (cat.), reflux, 3 h/EtOHMolecules 31 02197 i356[149]
113Molecules 31 02197 i357100 °C, 12 h/AcOHMolecules 31 02197 i358[150]
114Molecules 31 02197 i3591. reflux, 3 h/EtOHMolecules 31 02197 i360[151]
115Molecules 31 02197 i361rt, 3 h/MeOHMolecules 31 02197 i362[124]
116Molecules 31 02197 i363reflux/EtOHMolecules 31 02197 i364[152]
117Molecules 31 02197 i3651. AcOH (cat.), reflux, 2 h/EtOH
2. reflux, 8 h/AcOH		Molecules 31 02197 i366[64,153]
118Molecules 31 02197 i3671. rt, 3 h/MeOH
2. reflux, 4 h/EtOH
3. reflux, 2 h/EtOH		Molecules 31 02197 i368[124,154,155]
119Molecules 31 02197 i369reflux, 6 h/AcOH–EtOH (3:1)Molecules 31 02197 i370[68,69]
120Molecules 31 02197 i371Molecules 31 02197 i37260 °C, 8 h/CH2Cl2Molecules 31 02197 i373[156]
121Molecules 31 02197 i374reflux, 12 h/n-BuOHMolecules 31 02197 i375[110]
122Molecules 31 02197 i376R = H: 1. reflux, 1 h 30 min/MeOH
2. AcNH4 (cat.), reflux, 4 h/AcOH
R = Br: AcNH4 (cat.), reflux, 4 h/AcOH		Molecules 31 02197 i377[157,158]
123Molecules 31 02197 i378reflux, 12 h/AcOHMolecules 31 02197 i379[159]
124Molecules 31 02197 i380reflux, 12 h/AcOHMolecules 31 02197 i381[159,160]
125Molecules 31 02197 i382reflux, 12 h/n-BuOHMolecules 31 02197 i383[57]
126Molecules 31 02197 i384AcNH4 (cat.), reflux, 4 h/AcOHMolecules 31 02197 i385[158]
127Molecules 31 02197 i386120 °C, 12 h/AcOHMolecules 31 02197 i387[160]
128Molecules 31 02197 i388rt, 3 h/MeOHMolecules 31 02197 i389[124]
129Molecules 31 02197 i390120 °C, 8 h/AcOHMolecules 31 02197 i391[74]
130Molecules 31 02197 i392Molecules 31 02197 i393reflux, 9 h/EtOHMolecules 31 02197 i394[161]
131Molecules 31 02197 i3951. reflux, 15 min/EtOH
2. reflux, 1 h/EtOH		Molecules 31 02197 i396[162,163]
132Molecules 31 02197 i397reflux, 2 h/EtOHMolecules 31 02197 i398[164]
133Molecules 31 02197 i399CF3COOH, reflux, 14 h/EtOHMolecules 31 02197 i400[165]
134Molecules 31 02197 i401reflux, 12 h/AcOH–EtOH (1:1)Molecules 31 02197 i402[75]
135Molecules 31 02197 i4031. reflux, 5 h/AcOH
2. reflux, 4 h/EtOH		Molecules 31 02197 i404[28,166]
136Molecules 31 02197 i405Molecules 31 02197 i406reflux, 12 h/EtOHMolecules 31 02197 i407[167]
137Molecules 31 02197 i408reflux, 16 h/EtOHMolecules 31 02197 i409[167]
138Molecules 31 02197 i410Molecules 31 02197 i411125 °C, 12 h/AcOHMolecules 31 02197 i412[168]
139Molecules 31 02197 i413Molecules 31 02197 i414TsOH (cat.), reflux, 16 h/EtOHMolecules 31 02197 i415[27]
140Molecules 31 02197 i416R = H: TsOH (cat.), reflux, 16 h/EtOH
R = Br: 80 °C, 16 h/AcOH		Molecules 31 02197 i417[27,169]
141Molecules 31 02197 i418Molecules 31 02197 i419reflux, 6 h/EtOHMolecules 31 02197 i420[170]
142Molecules 31 02197 i421Molecules 31 02197 i422120 °C, 12 h/AcOHMolecules 31 02197 i423[171]
143Molecules 31 02197 i424Molecules 31 02197 i425120 °C, 12 h/AcOHMolecules 31 02197 i426[172]
144Molecules 31 02197 i427Molecules 31 02197 i428120 °C, 10 h/AcOHMolecules 31 02197 i429[160]
145Molecules 31 02197 i430Molecules 31 02197 i431R = H: reflux, 2 h/AcOH
R = Br: Zn(OAc)2 (cat.), 170 °C, 12 h/quinoline		Molecules 31 02197 i432[33,53]
146Molecules 31 02197 i433reflux, 12 h/AcOHMolecules 31 02197 i434[173]
147Molecules 31 02197 i435R = Br: 120 °C, 24 h/AcOH
R = CN: 80 °C, 19 h/AcOH–EtOH (1:1)		Molecules 31 02197 i436[34,174]
148Molecules 31 02197 i43780 °C, 15 h/AcOH–EtOH
(1:1)		Molecules 31 02197 i438[175]
149Molecules 31 02197 i439Molecules 31 02197 i440Do = C12H25AcOH (cat.), reflux, 24 h/EtOHMolecules 31 02197 i441[176]
150Molecules 31 02197 i442reflux, 12 h/AcOH–EtOH (1:1)Molecules 31 02197 i443[75]
151Molecules 31 02197 i44480 °C, 24 h/AcOH–CHCl3 (1:1)Molecules 31 02197 i445[76]
152Molecules 31 02197 i446Molecules 31 02197 i447reflux, 8 h/AcOHMolecules 31 02197 i448[35]
153Molecules 31 02197 i449Molecules 31 02197 i450reflux, 12 h/AcOHMolecules 31 02197 i451[173]
154Molecules 31 02197 i452reflux, 24 h/AcOHMolecules 31 02197 i453[177]
155Molecules 31 02197 i454Molecules 31 02197 i455100 °C, 192 h/DMSOMolecules 31 02197 i456[178]
156Molecules 31 02197 i457100 °C, 192 h/DMSOMolecules 31 02197 i458[178]
157Molecules 31 02197 i459Molecules 31 02197 i46080 °C, 15 h/AcOH–EtOH (1:1)Molecules 31 02197 i461[36]
158Molecules 31 02197 i462Molecules 31 02197 i463reflux, 12 h/AcOHMolecules 31 02197 i464[179]
159Molecules 31 02197 i465Molecules 31 02197 i466reflux, 8 h/AcOHMolecules 31 02197 i467[35]
160Molecules 31 02197 i468Molecules 31 02197 i469reflux, 2 h/AcOHMolecules 31 02197 i470[33]
161Molecules 31 02197 i471Molecules 31 02197 i472reflux, 12 h/AcOH–EtOH (1:1)Molecules 31 02197 i473[32]
162Molecules 31 02197 i474Molecules 31 02197 i475reflux, 3 h/AcOHMolecules 31 02197 i476[180]
163Molecules 31 02197 i477Molecules 31 02197 i47880 °C, 15 h/AcOH–EtOH
(1:1)		Molecules 31 02197 i479[175]
164Molecules 31 02197 i480Molecules 31 02197 i48175 °C, 24 h/AcOH–CHCl3 (1:1)Molecules 31 02197 i482[181]
Table 3. Structures of some polycycles and photovoltaic parameters of the solar cells based on them.
Table 3. Structures of some polycycles and photovoltaic parameters of the solar cells based on them.
StructureVoc, VJsc, mA·cm−1FF,%η, %Ref.
Molecules 31 02197 i4830.85927.7280.1219.09[202]
Molecules 31 02197 i4840.88925.8079.0618.14












[206]






















[206]
Molecules 31 02197 i4850.87226.4079.1718.21
Molecules 31 02197 i4860.88026.3678.2418.19
Molecules 31 02197 i4870.88625.8081.4518.62
Molecules 31 02197 i4880.90424.4875.8416.79
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MDPI and ACS Style

Verbitskiy, E.V.; Krynina, E.M.; Kvashnin, Y.A.; Charushin, V.N. 1,4-Diazatriphenylene and Its Hetero-Fused Analogs: Synthesis and Applications. Molecules 2026, 31, 2197. https://doi.org/10.3390/molecules31122197

AMA Style

Verbitskiy EV, Krynina EM, Kvashnin YA, Charushin VN. 1,4-Diazatriphenylene and Its Hetero-Fused Analogs: Synthesis and Applications. Molecules. 2026; 31(12):2197. https://doi.org/10.3390/molecules31122197

Chicago/Turabian Style

Verbitskiy, Egor V., Elizaveta M. Krynina, Yuriy A. Kvashnin, and Valery N. Charushin. 2026. "1,4-Diazatriphenylene and Its Hetero-Fused Analogs: Synthesis and Applications" Molecules 31, no. 12: 2197. https://doi.org/10.3390/molecules31122197

APA Style

Verbitskiy, E. V., Krynina, E. M., Kvashnin, Y. A., & Charushin, V. N. (2026). 1,4-Diazatriphenylene and Its Hetero-Fused Analogs: Synthesis and Applications. Molecules, 31(12), 2197. https://doi.org/10.3390/molecules31122197

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