Dyes and Pigments, volume 186, pages 109042

Imidazoporphyrins with appended polycyclic aromatic hydrocarbons: To conjugate or not to conjugate?

Publication typeJournal Article
Publication date2021-02-01
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor4.5
ISSN01437208, 18733743
General Chemical Engineering
Process Chemistry and Technology
Abstract
Herein we report the synthesis and characterization of a series of new dyads – imidazo-fused Ni(II) porphyrinates, containing polycyclic aromatic hydrocarbons (PAH) at the C-2 position of the imidazole ring, including pyrene – 1Pyr , anthracene – 1An , and diphenylanthracene – 1Ph 2 An . Electronic communication between the tetrapyrrolic macrocycles and PAH moieties was comprehensively studied by UV–Vis and fluorescence spectra together with quantum-chemical modelling. DFT calculations, including geometry optimization and analysis of the frontier orbitals, has revealed the efficient conjugation of pyrene and anthracene with porphyrin π-system, while 1Ph 2 An dyad possessed two isolated non-conjugated π-systems. Interestingly, these conclusions could not be unambiguously ruled out of UV–Vis spectroscopy data alone. Finally, the presence or absence of conjugation was confirmed using the analysis of ellipticities of bond critical points, thus proving this method to be a convenient tool to study the conjugation in multichromophoric porphyrin-based systems. • New porphyrin/polyaromatic hydrocarbon dyads. • Quantum-chemical rationalization of the electronic communication. • Tuning of the degree of conjugation.

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Birin K. P. et al. Imidazoporphyrins with appended polycyclic aromatic hydrocarbons: To conjugate or not to conjugate? // Dyes and Pigments. 2021. Vol. 186. p. 109042.
GOST all authors (up to 50) Copy
Birin K. P., Abdulaeva I. A., Polivanovskaia D. A., Martynov A. G., Shokurov A. V., Gorbunova Y. G., Tsivadze A. Imidazoporphyrins with appended polycyclic aromatic hydrocarbons: To conjugate or not to conjugate? // Dyes and Pigments. 2021. Vol. 186. p. 109042.
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RIS Copy
TY - JOUR
DO - 10.1016/j.dyepig.2020.109042
UR - https://doi.org/10.1016%2Fj.dyepig.2020.109042
TI - Imidazoporphyrins with appended polycyclic aromatic hydrocarbons: To conjugate or not to conjugate?
T2 - Dyes and Pigments
AU - Birin, Kirill P.
AU - Abdulaeva, Inna A
AU - Polivanovskaia, Daria A.
AU - Martynov, Alexander G.
AU - Shokurov, Alexander V.
AU - Gorbunova, Yulia G.
AU - Tsivadze, Aslan
PY - 2021
DA - 2021/02/01 00:00:00
PB - Elsevier
SP - 109042
VL - 186
SN - 0143-7208
SN - 1873-3743
ER -
BibTex
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BibTex Copy
@article{2021_Birin
author = {Kirill P. Birin and Inna A Abdulaeva and Daria A. Polivanovskaia and Alexander G. Martynov and Alexander V. Shokurov and Yulia G. Gorbunova and Aslan Tsivadze},
title = {Imidazoporphyrins with appended polycyclic aromatic hydrocarbons: To conjugate or not to conjugate?},
journal = {Dyes and Pigments},
year = {2021},
volume = {186},
publisher = {Elsevier},
month = {feb},
url = {https://doi.org/10.1016%2Fj.dyepig.2020.109042},
pages = {109042},
doi = {10.1016/j.dyepig.2020.109042}
}
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