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http://elar.urfu.ru/handle/10995/131336
Название: | Fluorescent Pyranoindole Congeners: Synthesis and Photophysical Properties of Pyrano[3,2-f], [2,3-g], [2,3-f], and [2,3-e]Indoles |
Авторы: | Sharapov, A. D. Fatykhov, R. F. Khalymbadzha, I. A. Valieva, M. I. Nikonov, I. L. Taniya, O. S. Kopchuk, D. S. Zyryanov, G. V. Potapova, A. P. Novikov, A. S. Sharutin, V. V. Chupakhin, O. N. |
Дата публикации: | 2022 |
Издатель: | MDPI |
Библиографическое описание: | Sharapov, AD, Fatykhov, RF, Khalymbadzha, IA, Valieva, MI, Nikonov, IL, Taniya, OS, Kopchuk, DS, Zyryanov, GV, Potapova, AP, Novikov, AS, Sharutin, VV & Chupakhin, ON 2022, 'Fluorescent Pyranoindole Congeners: Synthesis and Photophysical Properties of Pyrano[3,2-f], [2,3-g], [2,3-f], and [2,3-e]Indoles', Molecules, Том. 27, № 24, 8867. https://doi.org/10.3390/molecules27248867 Sharapov, A. D., Fatykhov, R. F., Khalymbadzha, I. A., Valieva, M. I., Nikonov, I. L., Taniya, O. S., Kopchuk, D. S., Zyryanov, G. V., Potapova, A. P., Novikov, A. S., Sharutin, V. V., & Chupakhin, O. N. (2022). Fluorescent Pyranoindole Congeners: Synthesis and Photophysical Properties of Pyrano[3,2-f], [2,3-g], [2,3-f], and [2,3-e]Indoles. Molecules, 27(24), [8867]. https://doi.org/10.3390/molecules27248867 |
Аннотация: | This paper reports the synthesis of four types of annulated pyranoindole congeners: pyrano[3,2-f]indole, pyrano[2,3-g]indole, pyrano[2,3-f]indole, and pyrano[2,3-e]indole and photophysical studies in this series. The synthesis of pyrano[3,2-f], [2,3-g], and [2,3-e]indoles involve a tandem of Bischler–Möhlau reaction of 3-aminophenol with benzoin to form 6-hydroxy- or 4-hydroxyindole followed by Pechmann condensation of these hydroxyindoles with β-ketoesters. Pyrano[2,3-f]indoles were synthesized through the Nenitzescu reaction of p-benzoquinone and ethyl aminocrotonates and subsequent Pechmann condensation of the obtained 5-hydroxyindole derivatives. Among the pyranoindoles studied, the most promising were pyrano[3,2-f] and [2,3-g]indoles. These compounds were characterized by moderate to high quantum yields (30–89%) and a large (9000–15,000 cm−1) Stokes shift. More detailed photophysical studies were carried out for a series of the most promising derivatives of pyrano[3,2-f] and [2,3-g]indoles to demonstrate their positive solvatochromism, and the data collected was analyzed using Lippert-Mataga equation. Quantum chemical calculations were performed to deepen the knowledge of the absorption and emission properties of pyrano[3,2-f] and [2,3-g]indoles as well as to explain their unusual geometries and electronic structures. © 2022 by the authors. |
Ключевые слова: | BISCHLER–MÖHLAU REACTION LIPPERT-MATAGA EQUATION NENITZESCU REACTION PECHMANN CONDENSATION PYRANOINDOLE STOKES SHIFT CHEMICAL PHENOMENA COLORING AGENTS INDOLES COLORING AGENT INDOLE DERIVATIVE CHEMICAL PHENOMENA CHEMISTRY |
URI: | http://elar.urfu.ru/handle/10995/131336 |
Условия доступа: | info:eu-repo/semantics/openAccess cc-by |
Текст лицензии: | https://creativecommons.org/licenses/by/4.0/ |
Идентификатор SCOPUS: | 85144510790 |
Идентификатор WOS: | 000904506700001 |
Идентификатор PURE: | 33229703 0138c900-dcce-42db-9def-a59671ba0d9e |
ISSN: | 1420-3049 |
DOI: | 10.3390/molecules27248867 |
Сведения о поддержке: | Russian Science Foundation, RSF, (21-13-00382, 8a –g) Council on grants of the President of the Russian Federation, (NSh-1223.2022.1.3) RUDN University This research was supported by the Russian Science Foundation (Project # 21-13-00382, synthesis of compounds 7a –g and 8a –g). Grigory V. Zyryanov is thankful to the Council for Grants of the President of the Russian Federation (photophysical investigation, Grant no. NSh-1223.2022.1.3). Alexander S. Novikov is grateful to RUDN University for support within the Strategic Academic Leadership Program. |
Карточка проекта РНФ: | 21-13-00382 |
Располагается в коллекциях: | Научные публикации ученых УрФУ, проиндексированные в SCOPUS и WoS CC |
Файлы этого ресурса:
Файл | Описание | Размер | Формат | |
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2-s2.0-85144510790.pdf | 14,63 MB | Adobe PDF | Просмотреть/Открыть |
Лицензия на ресурс: Лицензия Creative Commons