Modification of β-Octaethylporphyrin via Insertion of Amino and Azino Groups into meso-Positions

Andreeva, V.D.; Ponomarev, G.V.; Shkirdova, A.O.; Tyurin, V.S.; Zamilatskova, I.A.

Авторы: Andreeva Valeriia D., Ponomarev Gelii V., Shkirdova Alena O., Tyurin Vladimir S., Zamilatskova Ilya A.
Журнал: Макрогетероциклы
Том: 14
Номер: 3
Год издания: 2021
Издательство: Федеральное государственное бюджетное образовательное учреждение высшего образования "Ивановский государственный химико-технологический университет"
Местоположение издательства: Иваново
Первая страница: 201
Последняя страница: 207
DOI: 10.6060/mhc213990z
Аннотация: The functionalization of Ni(II) β-octaethylporphyrin was performed by introducing various amino and azino groups into meso-positions. Amino, n-propylamino, and trifluoromethylacetylamino groups were used as electron donor substituents, while azino group was inserted as an electron acceptor. The azine fragment was inserted through formylation followed by reaction with hydrazine and then with aromatic aldehydes, and the corresponding azine derivatives of p-nitrophenylbenzaldehyde and methyl pyropheophorbide d were obtained. It was found that under the conditions of formylation of meso-(trifluoroacetamido)-β-octaethylporphyrin, the amide fragment was oxidized to form hydroxamic acid. As a result of substitution of meso-positions of β-octaethylporphyrin, new functionalized porphyrin derivatives with significantly altered electron-optical properties were obtained. In particular, the azine bridged conjugate of β-octaethylporphyrin with methyl pyropheophorbide d was synthesized, the electronic absorption spectrum of which contains bathochromically shifted long-wavelength bands. The resulting compounds could be of interest as potential photosensitizers, sensor dyes and biologically active compounds.
Добавил в систему: Замилацков Илья Алексеевич

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Modification of β-Octaethylporphyrin via Insertion of Amino and Azino Groups into meso-Positionsстатья

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