Fluorescent Pyranoindole Congeners: Synthesis and Photophysical Properties of Pyrano[3,2-f], [2,3-g], [2,3-f], and [2,3-e]Indoles
Электронный научный архив УРФУ
Информация об архиве | Просмотр оригинала| Поле | Значение | |
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Fluorescent Pyranoindole Congeners: Synthesis and Photophysical Properties of Pyrano[3,2-f], [2,3-g], [2,3-f], and [2,3-e]Indoles
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| Автор |
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. |
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| Тематика |
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 |
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| Описание |
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.
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. |
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| Дата |
2024-04-08T11:06:41Z
2024-04-08T11:06:41Z 2022 |
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| Тип |
Article
Journal article (info:eu-repo/semantics/article) Published version (info:eu-repo/semantics/publishedVersion) |
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| Идентификатор |
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 1420-3049 Final All Open Access; Gold Open Access; Green Open Access https://www.mdpi.com/1420-3049/27/24/8867/pdf?version=1670987122 https://www.mdpi.com/1420-3049/27/24/8867/pdf?version=1670987122 http://elar.urfu.ru/handle/10995/131336 10.3390/molecules27248867 85144510790 000904506700001 |
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| Язык |
en
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| Связанные ресурсы |
info:eu-repo/grantAgreement/RSF//21-13-00382
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| Права |
Open access (info:eu-repo/semantics/openAccess)
cc-by https://creativecommons.org/licenses/by/4.0/ |
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| Формат |
application/pdf
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| Издатель |
MDPI
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| Источник |
Molecules
Molecules |
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