Pyropheophorbide-Fullerene Dyad: Synthesis and Photochemical Properties

Rybkin, A.Y.; Belik, A.Y.; Tarakanov, P.A.; Taziev, K.R.; Kozlov, A.V.; Goryachev, N.S.; Sulimenkov, I.V.; Kozlovskiy, V.I.; Romanenko, Y.V.; Koifman, O.I.; Kotelnikov, A.I.

Статья опубликована в журнале из списка RSCI Web of Science

Информация о цитировании статьи получена из Web of Science, Scopus
Статья опубликована в журнале из перечня ВАК
Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 20 декабря 2019 г.

Авторы: Rybkin A.Y., Belik A.Y., Tarakanov P.A., Taziev K.R., Kozlov A.V., Goryachev N.S., Sulimenkov I.V., Kozlovskiy V.I., Romanenko Y.V., Koifman O.I., Kotelnikov A.I.
Журнал: Макрогетероциклы
Том: 12
Номер: 2
Год издания: 2019
Издательство: Федеральное государственное бюджетное образовательное учреждение высшего образования "Ивановский государственный химико-технологический университет"
Местоположение издательства: Иваново
Первая страница: 181
Последняя страница: 186
DOI: 10.6060/mhc190446r
Аннотация: The methylpyropheophorbide-fullerene[60] dyad was synthesized by 1,3-dipolar cycloadditions of the corresponding azomethine ylide to C60 (Prato reaction). Using the mass spectrometric method with soft matrix-activated ionization it was possible to achieve a significant reduction in fragmentation processes by the retro-Diels-Alder reaction, which allows to reliably detect the presence of polyadducts of azomethine ylide cycloadditions to fullerene. The use of gel permeation chromatography under conditions of weakening of the intermolecular π-π interaction between methylpyropheophorbide and fullerene moieties makes it possible to effectively separate mixed products with ~ 1.5 fold difference in molecular weight. It has been shown that the fluorescence of the dyad is quenched more than 5000 times (compared to the native dye). The singlet oxygen quantum yield of the dyad is 360 times less than that for the native methylpyropheophorbide a, however, its efficiency of superoxide generation increases by 18.5 times. The obtained result agrees well with the previously reported mechanism of relaxation of the excited state of the dyad through a charge-separated state, which can lead to the formation of superoxide. The observed effects indicate a change in the mechanism of photodynamic activity from type II (generation of singlet oxygen) for the native dye to type I (generation of superoxide) for the dyad, which shows a promising method of creation of highly efficient photosensitizers based on similar dye-fullerene[60] dyads.
Добавил в систему: Котельников Александр Иванович

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Pyropheophorbide-Fullerene Dyad: Synthesis and Photochemical Propertiesстатья

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