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Macrocyclic Compounds: Derivatives and Applications

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Published Papers

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (31 January 2024) | Viewed by 16691

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Special Issue Editors

Prof. Dr. Yu G. Gorbunova

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Guest Editor

Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninskii pr. 31, 119991 Moscow, Russia
Interests: macrocyclic compounds; porphyrin; phthalocyanine; lanthanides; supramolecular chemistry; biomedicine

Dr. Alexander G. Martynov

E-Mail Website
Guest Editor

Frumkin Institute of Physical Chemistry and Electrochemistry of the Russian Academy of Sciences, Leninskii pr. 31-4, 119071 Moscow, Russia
Interests: phthalocyanine; lanthanides; magnetism; supramolecular chemistry

Special Issue Information

Dear Colleagues,

Macrocyclic compounds are widely exploited in both natural and artificial systems. Varying metal centers and tailoring substituents on the macrocycle the molecular structure of the complex can be precisely adapted to the target function and the operating environment. Macrocyclic ligands usually include mono- and polycyclic molecules with at least 12 atoms in the cycle and at least three atoms, as well as groups potentially able to coordinate with the complexing agent (e.g. metal cation). Due to the conformity of the diameter of the cation with the size and shape of the intramolecular cavity and the presence of several binding centers, the formation of macrocyclic coordination compounds occurs with high selectivity, and the complexes themselves are much more stable in comparison to complexes in which ligands are linear analogues of macrocyclic compounds (macrocyclic effect). The binding selectivity and stability of complexes with macrocyclic ligands also depend on the nature of the solvent, the charge of the integrating particle, the nature of the counterion and several other factors.

In recent years, there has been particular interest in the design of self-organizing, functional and hybrid systems that have become the basis for advanced materials, in particular smart materials with controlled and adaptive properties.

We present this Special Issue, entitled “Macrocyclic compounds: Derivatives and Applications”. This Special Issue has the broad scope required to provide an overview of current trends in the chemistry, physic and biology of macrocyclic compounds. Of particular importance are the synthesis, structural characterization, physical attributes, coordination and supramolecular chemistry of these compounds, as well as the practical application of all types of macrocycles and their derivatives.

Potential topics for this Special Issue will include, but are not limited to:

Synthetic approaches toward macrocyclic ligands and coordination compounds
Supramolecular chemistry of macrocyclic compounds
Molecular switchers and machines
Application of macrocycles and its derivatives.
Molecular recognition
Crystal engineering
Biomimetic and biomedical application

Researchers invite working in the field of macrocyclic chemistry are encouraged to contribute to this Special Issue and share their results with the scientific community. Both research articles and reviews can be submitted to the issue.

Prof. Dr. Yu G. Gorbunova
Dr. Alexander G. Martynov
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

macrocyclic compound
tetrapyrrols
porphyrin
phthalocyanine
crown-ethers
calixarene
supramolecular chemistry
biomedicine

Published Papers (14 papers)

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Research

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19 pages, 5380 KiB

Open AccessArticle

Synthetic Modifications of a Pb²⁺-Sensor Acridono-Crown Ether for Covalent Attachment and Their Effects on Selectivity

by Panna Vezse, Martin Gede, Ádám Golcs, Péter Huszthy and Tünde Tóth

Molecules 2024, 29(5), 1121; https://doi.org/10.3390/molecules29051121 - 01 Mar 2024

Viewed by 540

Abstract

Because of environmental impact, there is a great need for chemosensors, especially for toxic heavy metals such as lead. The conventional instrumental analytical techniques rarely provide an available real-time sensing platform, thus the development of highly selective and stable synthetic chemosensor molecules is of great importance. Acridono-18-crown-6 ethers have such properties, and much research has proven their outstanding applicability in various supramolecular devices. In this present work, we aimed to enable their covalent immobilization capability by synthesizing functionalized derivatives while preserving the favored molecular recognition ability. Several new macrocycle analogues were synthesized, while synthetization difficulties and design aspects were also dealt with. The selectivity of the macrocycle analogues was studied using UV–Vis spectroscopy and compared with that of the parent compounds. The ultimate crown ether derivative showed high Pb²⁺-selectivity, reversibility (decomplexation by extraction with water) and stability. Full article

(This article belongs to the Special Issue Macrocyclic Compounds: Derivatives and Applications)

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13 pages, 4944 KiB

Open AccessArticle

Synthesis and Dynamic Behavior of Ce(IV) Double-Decker Complexes of Sterically Hindered Phthalocyanines

by Jeevithra Dewi Subramaniam, Toshio Nishino, Kazuma Yasuhara and Gwénaël Rapenne

Molecules 2024, 29(4), 888; https://doi.org/10.3390/molecules29040888 - 17 Feb 2024

Viewed by 467

Abstract

Phthalocyanines and their double-decker complexes are interesting in designing rotative molecular machines, which are crucial for the development of molecular motors and gears. This study explores the design and synthesis of three bulky phthalocyanine ligands functionalized at the α-positions with phenothiazine or carbazole fragments, aiming to investigate dynamic rotational motions in these sterically hindered molecular complexes. Homoleptic and heteroleptic double-decker complexes were synthesized through the complexation of these ligands with Ce(IV). Notably, Ce^IV(Pc2)₂ and Ce^IV(Pc3)₂, both homoleptic complexes, exhibited blocked rotational motions even at high temperatures. The heteroleptic Ce^IV(Pc)(Pc3) complex, designed to lower symmetry, demonstrated switchable rotation along the pseudo-C₄ symmetry axis upon heating the solution. Variable-temperature ¹H-NMR studies revealed distinct dynamic behaviors in these complexes. This study provides insights into the rotational dynamics of sterically hindered double-decker complexes, paving the way for their use in the field of rotative molecular machines. Full article

(This article belongs to the Special Issue Macrocyclic Compounds: Derivatives and Applications)

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14 pages, 4922 KiB

Open AccessArticle

Synthesis and Properties of Novel Alkyl-Substituted Hexaazacyclophanes and Their Diradical Dications

by Shunjie Li and Jian Chen

Molecules 2024, 29(4), 789; https://doi.org/10.3390/molecules29040789 - 08 Feb 2024

Viewed by 642

Abstract

Radicals based on arylamine cyclophanes can be used as functional materials and show application potential in fields such as synthetic chemistry, molecular electronic components, organic light-emitting diodes, and catalytic chemistry. Using a Buchwald–Hartwig palladium-catalyzed aryl halide amination method, we synthesized a series of neutral hexaazacyclophane compounds 1–3 with different substituents in the meta–meta–meta positions of the phenyl rings. Three characteristic high-spin hexaazacyclophane diradical dications were obtained by two-electron oxidation using AgSbF₆: 1^2·+•2[SbF₆]⁻, 2^2·+•2[SbF₆]⁻, and 3^2·+•2[SbF₆]⁻. The electronic structures and physical properties of these compounds were then investigated by ¹H and ¹³C nuclear magnetic resonance spectroscopy, cyclic voltammetry, electron paramagnetic resonance spectroscopy, superconducting quantum interferometry, ultraviolet–visible spectroscopy, and density functional theory calculations. The findings provide new ideas for designing radical species with novel physical properties and electronic structures. Importantly, the obtained radical species are not sensitive to air, making them valuable functional materials for practical applications. Full article

(This article belongs to the Special Issue Macrocyclic Compounds: Derivatives and Applications)

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12 pages, 5995 KiB

Open AccessCommunication

Keto-Adamantane-Based Macrocycle Crystalline Supramolecular Assemblies Showing Selective Vapochromism to Tetrahydrofuran

by Zunhua Li, Yingzi Tan, Manhua Ding, Linli Tang and Fei Zeng

Molecules 2024, 29(3), 719; https://doi.org/10.3390/molecules29030719 - 04 Feb 2024

Viewed by 567

Abstract

Here, we report the synthesis of adamantane-based macrocycle 2 by combining adamantane building blocks with π-donor 1,3-dimethoxy-benzene units. An unpredictable keto-adamantane-based macrocycle 3 was obtained by the oxidation of 2 using DDQ as an oxidant. Moreover, a new type of macrocyclic molecule-based CT cocrystal was prepared through exo-wall CT interactions between 3 and DDQ. The cocrystal material showed selective vapochromism behavior towards THF, specifically, among nine volatile organic solvents commonly used in the laboratory. Powder X-ray diffraction; UV-Vis diffuse reflectance spectroscopy; ¹H NMR; and single crystal X-ray diffraction analyses revealed that color changes are attributed to the vapor-triggered decomplexation of cocrystals. Full article

(This article belongs to the Special Issue Macrocyclic Compounds: Derivatives and Applications)

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11 pages, 2947 KiB

Open AccessArticle

Tunable Supramolecular Ag⁺-Host Interactions in Pillar[n]arene[m]quinones and Ensuing Specific Binding to 1-Alkynes

by Yumei Zhu, Jorge Escorihuela, Haiying Wang, Andrew C.-H. Sue and Han Zuilhof

Molecules 2023, 28(20), 7009; https://doi.org/10.3390/molecules28207009 - 10 Oct 2023

Viewed by 1173

Abstract

We developed an improved, robust synthesis of a series of pillar[6]arenes with a varying number (0–3) of quinone moieties in the ring. This easy-to-control variation yielded a gradually less electron-rich cavity in going from zero to three quinone units, as shown from the strength of host–guest interactions with silver ions. Such macrocycle-Ag₂ complexes themselves were shown to display an unprecedented, sharp distinction between terminal alkynes, which strongly bound to such complexes, and internal alkynes, internal alkenes and terminal alkenes, which do hardly bind. Full article

(This article belongs to the Special Issue Macrocyclic Compounds: Derivatives and Applications)

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13 pages, 2499 KiB

Open AccessArticle

Synthesis, Structure, and Characterization of Thiacalix[4]-2,8-thianthrene

by Masafumi Ueda, Moe Isozaki and Yasuhiro Mazaki

Molecules 2023, 28(14), 5462; https://doi.org/10.3390/molecules28145462 - 17 Jul 2023

Viewed by 902

Abstract

Sulfur-containing macrocycles have attracted substantial interest because they exhibit unique characteristics due to their polygonal ring-shaped skeleton. In this study, a thianthrene-based cyclic tetramer with the sulfur linker, thiacalix[4]-2,8-thianthrene (TC[4]TT), was successfully prepared from a cyclo-p-phenylenesulfide derivative using acid-induced intramolecular condensation. Single crystal X-ray diffraction revealed that TC[4]TT adopts an alternative octagonal form recessed to the inner side. Its internal cavity included small solvents, such as chloroform and carbon disulfide. Due to its polygonal geometry, TC[4]TT laminated in a honeycomb-like pattern with a porous channel. Furthermore, TC[4]TT showed fluorescence and phosphorescence emission in a CH₂Cl₂ solution at ambient and liquid nitrogen temperatures. Both emission bands were slightly redshifted compared with those of the reference compounds (di(thanthren-2-yl)sulfane (TT₂S) and thianthrene (TT)). This work describes a sulfur-containing thiacalixheterocycle-based macrocyclic system with intriguing supramolecular chemistry based on molecular tiling and photophysical properties in solution. Full article

(This article belongs to the Special Issue Macrocyclic Compounds: Derivatives and Applications)

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9 pages, 2312 KiB

Open AccessArticle

Synthesis, Structures, and Magnetism of Four One-Dimensional Complexes Using [Ni(CN)₄]²⁻ and Macrocyclic Metal Complexes

by Guangchuan Ou, Qiong Wang, Yingzhi Tan and Qiang Zhou

Molecules 2023, 28(11), 4529; https://doi.org/10.3390/molecules28114529 - 02 Jun 2023

Viewed by 969

Abstract

Four one-dimensional complexes, denoted as [NiL₁][Ni(CN)₄] (1), [CuL₁][Ni(CN)₄] (2), [NiL₂][Ni(CN)₄]·2H₂O (3), and [CuL₂][Ni(CN)₄]·2H₂O (4) (L [...] Read more.

Four one-dimensional complexes, denoted as [NiL₁][Ni(CN)₄] (1), [CuL₁][Ni(CN)₄] (2), [NiL₂][Ni(CN)₄]·2H₂O (3), and [CuL₂][Ni(CN)₄]·2H₂O (4) (L₁ = 1,8-dimethyl-1,3,6,8,10,13-hexaaza-cyclotetradecane; L₂ = 1,8-dipropyl-1,3,6,8,10,13-hexaazacyclotetradecane) were synthesized by reacting nickel/copper macrocyclic complexes with K₂[Ni(CN)₄]. Subsequently, the synthesized complexes were characterized using elemental analysis, infrared spectroscopy analysis, thermogravimetric analysis, and X-ray powder diffraction. Single-crystal structure analysis revealed that the Ni(II)/Cu(II) atoms were coordinated by two nitrogen atoms from [Ni(CN)₄]²⁻ with four nitrogen atoms from a macrocyclic ligand, forming a six-coordinated octahedral coordination geometry. Nickel/copper macrocyclic complexes were bridged by [Ni(CN)₄]²⁻ to construct one-dimensional chain structures in 1–4. The characterization results showed that the four complexes obeyed the Curie–Weiss law with a weak antiferromagnetic exchange coupling. Full article

(This article belongs to the Special Issue Macrocyclic Compounds: Derivatives and Applications)

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11 pages, 2667 KiB

Open AccessArticle

Site-Selective Solvation-Induced Conformational Switching of Heteroleptic Heteronuclear Tb(III) and Y(III) Trisphthalocyaninates for the Control of Their Magnetic Anisotropy

by Alexander G. Martynov, Kirill P. Birin, Gayane A. Kirakosyan, Yulia G. Gorbunova and Aslan Yu. Tsivadze

Molecules 2023, 28(11), 4474; https://doi.org/10.3390/molecules28114474 - 31 May 2023

Cited by 1 | Viewed by 1004

Abstract

In the present work, we report the synthesis of isomeric heteronuclear terbium(III) and yttrium(III) triple-decker phthalocyaninates [(BuO)₈Pc]M[(BuO)₈Pc]M*[(15C5)₄Pc] (M = Tb, M* = Y or M = Y, M* = Tb, [(BuO)₈Pc]²⁻–octa-n-butoxyphthalocyaninato-ligand, [(15C5)₄Pc]²⁻–tetra-15-crown-5-phthalocyaninato-ligand). We show that these complexes undergo solvation-induced switching: the conformers in which both metal centers are in square-antiprismatic environments are stabilized in toluene, whereas in dichloromethane, the metal centers M and M* are in distorted prismatic and antiprismatic environments, respectively. This conclusion follows from the detailed analysis of lanthanide-induced shifts in ¹H NMR spectra, which makes it possible to extract the axial component of the magnetic susceptibility tensor

χ_{ax}^{Tb}

and to show that this term is particularly sensitive to conformational switching when terbium(III) ion is placed in the switchable “M” site. This result provides a new tool for controlling the magnetic properties of lanthanide complexes with phthalocyanine ligands. Full article

(This article belongs to the Special Issue Macrocyclic Compounds: Derivatives and Applications)

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15 pages, 4717 KiB

Open AccessArticle

Thiocarbonyl Derivatives of Natural Chlorins: Synthesis Using Lawesson’s Reagent and a Study of Their Properties

by Viktor Pogorilyy, Petr Ostroverkhov, Valeria Efimova, Ekaterina Plotnikova, Olga Bezborodova, Ekaterina Diachkova, Yuriy Vasil’ev, Andrei Pankratov and Mikhail Grin

Molecules 2023, 28(10), 4215; https://doi.org/10.3390/molecules28104215 - 20 May 2023

Cited by 1 | Viewed by 1549

Abstract

The development of sulfur-containing pharmaceutical compounds is important in the advancement of medicinal chemistry. Photosensitizers (PS) that acquire new properties upon incorporation of sulfur-containing groups or individual sulfur atoms into their structure are not neglected, either. In this work, a synthesis of sulfur-containing derivatives of natural chlorophyll a using Lawesson’s reagent was optimized. Thiocarbonyl chlorins were shown to have a significant bathochromic shift in the absorption and fluorescence bands. The feasibility of functionalizing the thiocarbonyl group at the macrocycle periphery by formation of a Pt(II) metal complex in the chemotherapeutic agent cisplatin was shown. The chemical stability of the resulting conjugate in aqueous solution was studied, and it was found to possess a high cytotoxic activity against sarcoma S37 tumor cells that results from the combined photodynamic and chemotherapeutic effect on these cells. Full article

(This article belongs to the Special Issue Macrocyclic Compounds: Derivatives and Applications)

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13 pages, 2258 KiB

Open AccessArticle

Tuning Photochemical and Photophysical Properties of P(V) Phthalocyanines

by Evgeniya A. Safonova, Filipp M. Kolomeychuk, Daniil A. Gvozdev, Aslan Yu. Tsivadze and Yulia G. Gorbunova

Molecules 2023, 28(3), 1094; https://doi.org/10.3390/molecules28031094 - 21 Jan 2023

Cited by 2 | Viewed by 1359

Abstract

The ability of P(V) phthalocyanines (Pcs) for efficient singlet oxygen (SO) generation was demonstrated for the first time by the example of unsubstituted and α- and β-octabutoxy-substituted P(V)Pcs with hydroxy, methoxy and phenoxy ligands in the apical positions of the octahedral P centre. Variation of substituents in Pc ring and P(V) axial ligands allows careful tuning of photophysical and photochemical properties. Indeed, a combination of BuO groups in the β-positions of the Pc ring and PhO groups as axial ligands provides significant SO generation quantum yields up to 90%; meanwhile, the values of SO generation quantum yields for others investigated compounds vary from 27 to 55%. All the complexes, except α-substituted P(V)Pc, demonstrate fluorescence with moderate quantum yields (10–16%). The introduction of electron-donating butoxy groups, especially in the α-position, increases the photostability of P(V)Pcs. Moreover, it has been shown in the example of β-BuO-substituted P(V) that the photostability depends on the nature of axial ligands and increases in the next row: OPh < OMe < OH. The presence of oxy/hydroxy axial ligands on the P(V) atom makes it possible to switch the photochemical and photophysical properties of P(V)Pcs by changing the acidity of the media. Full article

(This article belongs to the Special Issue Macrocyclic Compounds: Derivatives and Applications)

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18 pages, 6395 KiB

Open AccessArticle

Study of Lithium-Extraction Systems Based on Benzo-15-Crown-5 Ether and Alkylimidazolium-Based Ionic Liquid

by Alexey A. Bezdomnikov, Liudmila I. Demina, Lyudmila G. Kuz’mina, Galina V. Kostikova, Valeriy I. Zhilov and Aslan Yu. Tsivadze

Molecules 2023, 28(3), 935; https://doi.org/10.3390/molecules28030935 - 17 Jan 2023

Cited by 3 | Viewed by 1570

Abstract

The extraction of lithium from aqueous solutions of LiNTf₂ and LiCl salts using benzo-15-crown-5 ether (B15C5) as an extractant in [C8mim][NTf₂] ionic liquid was studied. The transition of the extractant into the aqueous phase and the distribution of Cl⁻ ions during lithium extraction from LiCl solutions were determined. LiNTf₂ complexes with B15C5 with different LiNTf₂:B15C5 ratios were isolated for the first time and characterized via X-ray diffraction and IR spectroscopy. Differences in the extraction process of LiCl and LiNTf₂ were determined via an infrared spectroscopic study of the extraction systems. Full article

(This article belongs to the Special Issue Macrocyclic Compounds: Derivatives and Applications)

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Review

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26 pages, 25075 KiB

Open AccessReview

Bismacrocycle: Structures and Applications

by Xu-Lang Chen, Si-Qian Yu, Xiao-Huan Huang and Han-Yuan Gong

Molecules 2023, 28(16), 6043; https://doi.org/10.3390/molecules28166043 - 13 Aug 2023

Cited by 4 | Viewed by 1044

Abstract

In the past half-century, macrocycles with different structures and functions, have played a critical role in supramolecular chemistry. Two macrocyclic moieties can be linked to form bismacrocycle molecules. Compared with monomacrocycle, the unique structures of bismacrocycles led to their specific recognition and assembly properties, also a wide range of applications, including molecular recognition, supramolecular self-assembly, advanced optical material construction, etc. In this review, we focus on the structure of bismacrocycle and their applications. Our goal is to summarize and outline the possible future development directions of bismacrocycle research. Full article

(This article belongs to the Special Issue Macrocyclic Compounds: Derivatives and Applications)

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39 pages, 12036 KiB

Open AccessReview

Meso-Formyl, Vinyl, and Ethynyl Porphyrins—Multipotent Synthons for Obtaining a Diverse Array of Functional Derivatives

by Vladimir S. Tyurin, Alena O. Shkirdova, Oscar I. Koifman and Ilya A. Zamilatskov

Molecules 2023, 28(15), 5782; https://doi.org/10.3390/molecules28155782 - 31 Jul 2023

Viewed by 1197

Abstract

This review presents a strategy for obtaining various functional derivatives of tetrapyrrole compounds based on transformations of unsaturated carbon-oxygen and carbon-carbon bonds of the substituents at the meso position (meso-formyl, vinyl, and ethynyl porphyrins). First, synthetic approaches to the preparation of these precursors are described. Then diverse pathways for the transformations of the multipotent synthons are discussed, revealing a variety of products of such reactions. The structures, electronic, and optical properties of the compounds obtained by the methods under consideration are analyzed. In addition, there is an overview of the applications of the products obtained. Biomedical use of the compounds is among the most important. Finally, the advantages of using the reviewed synthetic strategy to obtain dyes with targeted properties are highlighted. Full article

(This article belongs to the Special Issue Macrocyclic Compounds: Derivatives and Applications)

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22 pages, 19926 KiB

Open AccessReview

Recent Progress in Porphyrin/g-C₃N₄ Composite Photocatalysts for Solar Energy Utilization and Conversion

by Sudi Chen, Jiajia Wei, Xitong Ren, Keke Song, Jiajie Sun, Feng Bai and Shufang Tian

Molecules 2023, 28(11), 4283; https://doi.org/10.3390/molecules28114283 - 23 May 2023

Cited by 8 | Viewed by 2125

Abstract

Transforming solar energy into chemical bonds is a promising and viable way to store solar energy. Porphyrins are natural light-capturing antennas, and graphitic carbon nitride (g-C₃N₄) is an effective, artificially synthesized organic semiconductor. Their excellent complementarity has led to a growing number of research papers on porphyrin/g-C₃N₄ hybrids for solar energy utilization. This review highlights the recent progress in porphyrin/g-C₃N₄ composites, including: (1) porphyrin molecules/g-C₃N₄ composite photocatalysts connected via noncovalent or covalent interactions, and (2) porphyrin-based nanomaterials/g-C₃N₄ composite photocatalysts, such as porphyrin-based MOF/g-C₃N₄, porphyrin-based COF/g-C₃N₄, and porphyrin-based assembly/g-C₃N₄ heterojunction nanostructures. Additionally, the review discusses the versatile applications of these composites, including artificial photosynthesis for hydrogen evolution, CO₂ reduction, and pollutant degradation. Lastly, critical summaries and perspectives on the challenges and future directions in this field are also provided. Full article

(This article belongs to the Special Issue Macrocyclic Compounds: Derivatives and Applications)

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