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The Advances of Metallophthalocyanines
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The Advances of Metallophthalocyanines

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

Deadline for manuscript submissions: closed (15 November 2022) | Viewed by 11726

Special Issue Editor

Prof. Dr. Jan Janczak

E-Mail Website1 Website2
Guest Editor
Institute of Low Temperature and Structure Research, Polish Academy of Sciences, P.O. Box 1410, Okólna 2 Str., 50-950 Wrocław, Poland
Interests: metallophthalocyanines; metal-organic frameworks (MOF); hydrogen bonds; organic frameworks (OF); medicinal chemistry; crystallization; structural chemistry; crystallography; crystal engineering; synthesis; catalysis; theoretical chemistry; computational chemistry; coordination chemistry; inorganic biochemistry; bioinorganic chemistry

Special Issue Information

Dear Colleagues,

Metallophthalocyanines (MPcs) have been the subject of intense research interest since their initial characterization in the 1930s after their accidental formation during the industrial production of phthalimide from phthalic anhydride. MPcs containing an extended 18π-electron-conjugated aromatic system exhibit unique electronic and optical properties. Due to their fascinating and various properties as well as their high thermal and chemical stability, they are a very important class of compounds that offer varied and diverse applications. The continuously increasing interest in metallophthalocyanines is also due to their exceptional photophysical, photochemical, and electrochemical properties, which provide opportunities for their application in dyes and pigments, gas sensors, solar cells, non-linear optics, optical data storage devices, near-IR imaging agents, active matrix displays, and organic light-emitting diodes (OLEDs). Many metallophthalocyanines and their derivatives with low toxicity have been confirmed to be quite promising as photosensitizers for PDT, in view of their strong intense absorption in the therapeutic window, in the red region of visible light. An influential photosensitizer for PDT application should be characterized by high singlet oxygen generation capacity, high triplet-state quantum yields, and long triplet life-time. The limited solubility of large planar metallophthalocyanines and the aggregation behavior in biological systems are very common phenomena in this family of compounds due to the π–π interactions between the molecules with extended π-electron-delocalized systems that decrease their fluorescence quantum yields, shorten their triplet lifetime, and reduce their photosensitizing efficiency. Therefore, many researchers are still searching for new ways to functionalize them, so as to obtain metallophthalocyanines with the desired properties determining their application. The main aim of this Special Issue "The Advance of Metallophthalocyanines" is to create an open forum where scientists can share their research and discoveries in this promising field and, owing to the open-access platform, increase their visibility and the chances of interaction with industries and production systems. The contributions to this Issue, in the form of original research or review articles, may cover all aspects of metallophthalocyanines; research with interdisciplinary input is especially welcome, giving new insights into metallophthalocyanines.

Prof. Dr. Jan Janczak
Guest Editor

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Keywords

  • Functionalization of metallophthalocyanines
  • Metallophthalocyanines structure–properties relationships
  • Catalytic properties of metallophthalocyanines
  • Axially ligated metallophthalocyanines and related conjugated systems
  • Metallophthalocyanines as photosensitizers for photodynamic therapy
  • Non-planar metallophthalocyanines
  • Metallophthalocyanines for NLO applications
  • Metallophthalocyanines-based nanomaterials

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Published Papers (4 papers)

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Research

17 pages, 4179 KiB  
Article
Synthesis, Structure, and UV–Vis Characterization of Antimony(III) Phthalocyanine: [(SbPc)2(Sb2I8)(SbBr3)]2
by Ryszard Kubiak and Jan Janczak
Molecules 2022, 27(6), 1839; https://doi.org/10.3390/molecules27061839 - 11 Mar 2022
Cited by 2 | Viewed by 2612
Abstract
A new antimony(III)–phthalocyanine complex with the formula of [(SbPc)2(Sb2I8)(SbBr3)]2 has been obtained in the reaction of pure antimony powder with phthalonitrile under the oxidation conditions by iodine monobromide vapors. The complex crystallizes in the [...] Read more.
A new antimony(III)–phthalocyanine complex with the formula of [(SbPc)2(Sb2I8)(SbBr3)]2 has been obtained in the reaction of pure antimony powder with phthalonitrile under the oxidation conditions by iodine monobromide vapors. The complex crystallizes in the centrosymmetric space group of the triclinic system. Both independent (SbPc)+ units exhibit non-planar conformation, since the Sb(III) is larger than the equilibrium cavity size of the ring and cannot be accommodated without its expansion; thus, the metal protrudes out of the cavity, forming a saucer shape. The centrosymmetric anionic unit of the crystal consists of two (Sb2I8)2− interacted anionic units forming (Sb4I16)4− anionic complex that interacts with two SbBr3 molecules to form [Sb6I16Br6]4− anionic aggregate. Each [Sb6I16Br6]4− anionic aggregate is surrounded by four (SbPc)+ cations forming a supramolecular centrosymmetric (SbPc)4[Sb6I16Br6] complex. Translationally related (SbPc)4[Sb6I16Br6] molecules form a stacking structure along the [100] and [011] directions with N4–N4 distances of 3.55 and 3.53 Å, respectively, between the back-to-back-oriented saucer-shaped (SbPc)+ units. The interaction between the building units of the crystal was analyzed using the Hirshfeld surface and the analysis of the 2D fingerprint plots. The UV–Vis absorption spectra of crystal 1 were taken in CH2Cl2 and toluene solutions in the concentration range from 10−5 to 10−6 mol/L. No significant changes related to aggregation in solutions were observed. The Q-band in toluene solution is red shifted by ~15 nm in comparison to that in CH2Cl2 solution. Oxidation of (SbPc)4[Sb6I16Br6] yields SbVPc derivative. Both SbIII and SbV phthalocyanine derivatives absorb near infrared light (600–900 nm), which should be intriguing from the point of view of potential use as photosensitizers for PDT and as an infrared cut filter for plasma display and silicon photodiodes. Full article
(This article belongs to the Special Issue The Advances of Metallophthalocyanines)
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18 pages, 3732 KiB  
Article
Tetra-2,3-Pyrazinoporphyrazines with Externally Appended Pyridine Rings 22 Synthesis, Physicochemical and Photoactivity Studies on In(III) Mono- and Heteropentanuclear Complexes
by Maria Pia Donzello, Giulia Capobianco, Ida Pettiti, Claudio Ercolani and Pavel A. Stuzhin
Molecules 2022, 27(3), 849; https://doi.org/10.3390/molecules27030849 - 27 Jan 2022
Cited by 4 | Viewed by 2523
Abstract
The basic macrocyclic octapyridinotetrapyrazinoporphyrazine InIII complex of formula [Py8TPyzPzIn(OAc)]·8H2O, prepared by reaction of the free ligand [Py8TPyzPzH2]·2H2O with In(OAc)3, is a stable-to-air species of which the structure has been studied [...] Read more.
The basic macrocyclic octapyridinotetrapyrazinoporphyrazine InIII complex of formula [Py8TPyzPzIn(OAc)]·8H2O, prepared by reaction of the free ligand [Py8TPyzPzH2]·2H2O with In(OAc)3, is a stable-to-air species of which the structure has been studied by its X-ray powder diffraction and mass spectra and characterization operated by IR and UV-visible spectral behavior. The complex has been further examined and proven to be of potential interest for its response as an anticancer agent in the field of photodynamic therapy (PDT), the value of ΦΔ = 0.55 (in DMF) being in the range of 0.4–0.6 at the level of similar phthalocyanine and porphyrazine analogs and qualifying the species as a highly efficient anticancer agent. Planned parallel types of investigation, including their photoactive behaviour in PDT, have been extended to the mononuclear octacation [(2-Mepy)8TPyzPzIn(OAc)]8+ (salted by iodide ions) and the heteropentanuclear derivatives [(M’Cl2)4Py8TPyzPzIn(OAc)]·xH2O (M’ = PdII, x = 8; PtII, x = 1)) and [{(Pd(CBT)2)4}Py8TPyzPzIn(OAc)]·19H2O (CBT = m-carborane-1-thiolate anion). Full article
(This article belongs to the Special Issue The Advances of Metallophthalocyanines)
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14 pages, 3515 KiB  
Article
Synthesis, Spectroscopic Properties and Redox Behavior Kinetics of Rare-Earth Bistetrakis-4-[3-(3,4-dicyanophenoxy)phenoxy]phthalocyaninato Metal Complexes with Er, Lu and Yb
by Dmitry A. Erzunov, Anna A. Botnar, Natalia P. Domareva, Tatiana V. Tikhomirova and Arthur S. Vashurin
Molecules 2021, 26(8), 2181; https://doi.org/10.3390/molecules26082181 - 10 Apr 2021
Cited by 7 | Viewed by 2379
Abstract
Novel bistetrakis-4-[3-(3,4-dicyanophenoxy)phenoxy]phthalocyaninato of complexes erbium, lutetium and ytterbium were synthesized using a template fusion method to prevent any polymerization process. The complexes were separated from the reaction mixtures and characterized by NMR, IR and electron absorption spectroscopy. The spectroscopic properties of the metal [...] Read more.
Novel bistetrakis-4-[3-(3,4-dicyanophenoxy)phenoxy]phthalocyaninato of complexes erbium, lutetium and ytterbium were synthesized using a template fusion method to prevent any polymerization process. The complexes were separated from the reaction mixtures and characterized by NMR, IR and electron absorption spectroscopy. The spectroscopic properties of the metal phthalocyaninates in chloroform, acetone and tetrahydrofuran were studied. The regular bathochromic shift in the Er–Yb–Lu series was determined. In acetone medium all the complexes obtained were found to exist in an equilibrium state between neutral and reduced forms. The linearity of Lambert-Bouger-Beer curves makes it possible to study the kinetics of redox processes in the presence of phenylhydrazine and bromine. The lutetium complex showed better reducing properties and turned fully into the reduced form, while the erbium and ytterbium ones changed only partially. Upon oxidizing all the phthalocyaninates transformed into a mixture of oxidized and neutral-radical forms. The extinction coefficients and effective redox constants were calculated. Full article
(This article belongs to the Special Issue The Advances of Metallophthalocyanines)
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13 pages, 4524 KiB  
Article
Tuning the Covering on Gold Surfaces by Grafting Amino-Aryl Films Functionalized with Fe(II) Phthalocyanine: Performance on the Electrocatalysis of Oxygen Reduction
by Camila F. Olguín, Nicolás Agurto, Carlos P. Silva, Carolina P. Candia, Mireya Santander-Nelli, Juan Oyarzo, Alejandra Gómez, Juan F. Silva and Jorge Pavez
Molecules 2021, 26(6), 1631; https://doi.org/10.3390/molecules26061631 - 15 Mar 2021
Cited by 3 | Viewed by 3345
Abstract
Current selective modification methods, coupled with functionalization through organic or inorganic molecules, are crucial for designing and constructing custom-made molecular materials that act as electroactive interfaces. A versatile method for derivatizing surfaces is through an aryl diazonium salt reduction reaction (DSRR). A prominent [...] Read more.
Current selective modification methods, coupled with functionalization through organic or inorganic molecules, are crucial for designing and constructing custom-made molecular materials that act as electroactive interfaces. A versatile method for derivatizing surfaces is through an aryl diazonium salt reduction reaction (DSRR). A prominent feature of this strategy is that it can be carried out on various materials. Using the DSRR, we modified gold surface electrodes with 4-aminebenzene from 4-nitrobenzenediazonium tetrafluoroborate (NBTF), regulating the deposited mass of the aryl film to achieve covering control on the electrode surface. We got different degrees of covering: monolayer, intermediate, and multilayer. Afterwards, the ArNO2 end groups were electrochemically reduced to ArNH2 and functionalized with Fe(II)-Phthalocyanine to study the catalytic performance for the oxygen reduction reaction (ORR). The thickness of the electrode covering determines its response in front of ORR. Interestingly, the experimental results showed that an intermediate covering film presents a better electrocatalytic response for ORR, driving the reaction by a four-electron pathway. Full article
(This article belongs to the Special Issue The Advances of Metallophthalocyanines)
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