Switchable Aromaticity of Phthalocyanine via Reversible Nucleophilic Aromatic Addition to an Electron-Deficient Phosphorus(V) Complex
Filipp M Kolomeychuk
1, 2
,
Gayane Kirakosyan
1, 2
,
Gayane A. Kirakosyan
1, 2
,
Aslan Tsivadze
1, 2
,
Aslan Yu. Tsivadze
1, 2
,
Yulia G. Gorbunova
1, 2
Publication type: Journal Article
Publication date: 2021-08-23
scimago Q1
wos Q1
SJR: 5.554
CiteScore: 22.5
Impact factor: 15.6
ISSN: 00027863, 15205126
PubMed ID:
34423977
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
Reversible nucleophilic addition to a phthalocyanine core was observed for the first time for the electron-deficient cationic phosphorus(V) complex [PcP(OMe)2]+, whose reaction with KOH afforded a highly distorted nonaromatic adduct bearing an OH group at one of the α-pyrrolic carbon atoms. This adduct was characterized by single-crystal X-ray diffraction, ESI HRMS, and NMR, and UV-vis spectroscopy, together with quantum-chemical modeling. The acidic treatment of this adduct restored aromaticity and recovered the starting cationic complex. The reversible aromaticity breakage resulted in dramatic changes in the photophysical properties of the studied complex, which could pave the way to novel switchable Pc-based compounds and materials.
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Citations from 2024:
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GOST
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Kolomeychuk F. M. et al. Switchable Aromaticity of Phthalocyanine via Reversible Nucleophilic Aromatic Addition to an Electron-Deficient Phosphorus(V) Complex // Journal of the American Chemical Society. 2021. Vol. 143. No. 35. pp. 14053-14058.
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Kolomeychuk F. M., Safonova E. A., Polovkova M. A., Sinelshchikova A., Martynov A. G., Shokurov A. V., Kirakosyan G., Kirakosyan G. A., Efimov N. N., Tsivadze A., Tsivadze A. Y., Gorbunova Y. G. Switchable Aromaticity of Phthalocyanine via Reversible Nucleophilic Aromatic Addition to an Electron-Deficient Phosphorus(V) Complex // Journal of the American Chemical Society. 2021. Vol. 143. No. 35. pp. 14053-14058.
Cite this
RIS
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TY - JOUR
DO - 10.1021/jacs.1c05831
UR - https://pubs.acs.org/doi/10.1021/jacs.1c05831
TI - Switchable Aromaticity of Phthalocyanine via Reversible Nucleophilic Aromatic Addition to an Electron-Deficient Phosphorus(V) Complex
T2 - Journal of the American Chemical Society
AU - Kolomeychuk, Filipp M
AU - Safonova, Evgeniya A.
AU - Polovkova, Marina A
AU - Sinelshchikova, Anna
AU - Martynov, Alexander G.
AU - Shokurov, Alexander V.
AU - Kirakosyan, Gayane
AU - Kirakosyan, Gayane A.
AU - Efimov, Nikolay N.
AU - Tsivadze, Aslan
AU - Tsivadze, Aslan Yu.
AU - Gorbunova, Yulia G.
PY - 2021
DA - 2021/08/23
PB - American Chemical Society (ACS)
SP - 14053-14058
IS - 35
VL - 143
PMID - 34423977
SN - 0002-7863
SN - 1520-5126
ER -
Cite this
BibTex (up to 50 authors)
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@article{2021_Kolomeychuk,
author = {Filipp M Kolomeychuk and Evgeniya A. Safonova and Marina A Polovkova and Anna Sinelshchikova and Alexander G. Martynov and Alexander V. Shokurov and Gayane Kirakosyan and Gayane A. Kirakosyan and Nikolay N. Efimov and Aslan Tsivadze and Aslan Yu. Tsivadze and Yulia G. Gorbunova},
title = {Switchable Aromaticity of Phthalocyanine via Reversible Nucleophilic Aromatic Addition to an Electron-Deficient Phosphorus(V) Complex},
journal = {Journal of the American Chemical Society},
year = {2021},
volume = {143},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://pubs.acs.org/doi/10.1021/jacs.1c05831},
number = {35},
pages = {14053--14058},
doi = {10.1021/jacs.1c05831}
}
Cite this
MLA
Copy
Kolomeychuk, Filipp M., et al. “Switchable Aromaticity of Phthalocyanine via Reversible Nucleophilic Aromatic Addition to an Electron-Deficient Phosphorus(V) Complex.” Journal of the American Chemical Society, vol. 143, no. 35, Aug. 2021, pp. 14053-14058. https://pubs.acs.org/doi/10.1021/jacs.1c05831.