Fluorescent Pyranoindole Congeners: Synthesis and Photophysical Properties of Pyrano[3,2-<i>f</i>], [2,3-<i>g</i>], [2,3-<i>f</i>], and [2,3-<i>e</i>]Indoles
This paper reports the synthesis of four types of annulated pyranoindole congeners: pyrano[3,2-<i>f</i>]indole, pyrano[2,3-<i>g</i>]indole, pyrano[2,3-<i>f</i>]indole, and pyrano[2,3-<i>e</i>]indole and photophysical studies in this series. The synthes...
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MDPI AG
2022-12-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/24/8867 |
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| author | Ainur D. Sharapov Ramil F. Fatykhov Igor A. Khalymbadzha Maria I. Valieva Igor L. Nikonov Olga S. Taniya Dmitry S. Kopchuk Grigory V. Zyryanov Anastasya P. Potapova Alexander S. Novikov Vladimir V. Sharutin Oleg N. Chupakhin |
| author_facet | Ainur D. Sharapov Ramil F. Fatykhov Igor A. Khalymbadzha Maria I. Valieva Igor L. Nikonov Olga S. Taniya Dmitry S. Kopchuk Grigory V. Zyryanov Anastasya P. Potapova Alexander S. Novikov Vladimir V. Sharutin Oleg N. Chupakhin |
| author_sort | Ainur D. Sharapov |
| collection | DOAJ |
| description | This paper reports the synthesis of four types of annulated pyranoindole congeners: pyrano[3,2-<i>f</i>]indole, pyrano[2,3-<i>g</i>]indole, pyrano[2,3-<i>f</i>]indole, and pyrano[2,3-<i>e</i>]indole and photophysical studies in this series. The synthesis of pyrano[3,2-<i>f</i>], [2,3-<i>g</i>], and [2,3-<i>e</i>]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-<i>f</i>]indoles were synthesized through the Nenitzescu reaction of <i>p</i>-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-<i>f</i>] and [2,3-<i>g</i>]indoles. These compounds were characterized by moderate to high quantum yields (30–89%) and a large (9000–15,000 cm<sup>−1</sup>) Stokes shift. More detailed photophysical studies were carried out for a series of the most promising derivatives of pyrano[3,2-<i>f</i>] and [2,3-<i>g</i>]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-<i>f</i>] and [2,3-<i>g</i>]indoles as well as to explain their unusual geometries and electronic structures. |
| first_indexed | 2024-03-09T16:02:44Z |
| format | Article |
| id | doaj.art-e522a20ca6c84f6b8dab0b836d1a8fb7 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T16:02:44Z |
| publishDate | 2022-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-e522a20ca6c84f6b8dab0b836d1a8fb72023-11-24T16:58:47ZengMDPI AGMolecules1420-30492022-12-012724886710.3390/molecules27248867Fluorescent Pyranoindole Congeners: Synthesis and Photophysical Properties of Pyrano[3,2-<i>f</i>], [2,3-<i>g</i>], [2,3-<i>f</i>], and [2,3-<i>e</i>]IndolesAinur D. Sharapov0Ramil F. Fatykhov1Igor A. Khalymbadzha2Maria I. Valieva3Igor L. Nikonov4Olga S. Taniya5Dmitry S. Kopchuk6Grigory V. Zyryanov7Anastasya P. Potapova8Alexander S. Novikov9Vladimir V. Sharutin10Oleg N. Chupakhin11Department of Organic and Biomolecular Chemistry, Ural Federal University, Mira Street 19, 620002 Ekaterinburg, RussiaDepartment of Organic and Biomolecular Chemistry, Ural Federal University, Mira Street 19, 620002 Ekaterinburg, RussiaDepartment of Organic and Biomolecular Chemistry, Ural Federal University, Mira Street 19, 620002 Ekaterinburg, RussiaDepartment of Organic and Biomolecular Chemistry, Ural Federal University, Mira Street 19, 620002 Ekaterinburg, RussiaDepartment of Organic and Biomolecular Chemistry, Ural Federal University, Mira Street 19, 620002 Ekaterinburg, RussiaDepartment of Organic and Biomolecular Chemistry, Ural Federal University, Mira Street 19, 620002 Ekaterinburg, RussiaDepartment of Organic and Biomolecular Chemistry, Ural Federal University, Mira Street 19, 620002 Ekaterinburg, RussiaDepartment of Organic and Biomolecular Chemistry, Ural Federal University, Mira Street 19, 620002 Ekaterinburg, RussiaDepartment of Organic and Biomolecular Chemistry, Ural Federal University, Mira Street 19, 620002 Ekaterinburg, RussiaInstitute of Chemistry, Saint Petersburg State University, Universitetskaya Emb., 7/9, 199034 Saint Petersburg, RussiaDepartment of Chemistry, Institute of Natural Sciences, South Ural State University (National Research University), Lenin Avenue 76, 454080 Chelyabinsk, RussiaDepartment of Organic and Biomolecular Chemistry, Ural Federal University, Mira Street 19, 620002 Ekaterinburg, RussiaThis paper reports the synthesis of four types of annulated pyranoindole congeners: pyrano[3,2-<i>f</i>]indole, pyrano[2,3-<i>g</i>]indole, pyrano[2,3-<i>f</i>]indole, and pyrano[2,3-<i>e</i>]indole and photophysical studies in this series. The synthesis of pyrano[3,2-<i>f</i>], [2,3-<i>g</i>], and [2,3-<i>e</i>]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-<i>f</i>]indoles were synthesized through the Nenitzescu reaction of <i>p</i>-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-<i>f</i>] and [2,3-<i>g</i>]indoles. These compounds were characterized by moderate to high quantum yields (30–89%) and a large (9000–15,000 cm<sup>−1</sup>) Stokes shift. More detailed photophysical studies were carried out for a series of the most promising derivatives of pyrano[3,2-<i>f</i>] and [2,3-<i>g</i>]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-<i>f</i>] and [2,3-<i>g</i>]indoles as well as to explain their unusual geometries and electronic structures.https://www.mdpi.com/1420-3049/27/24/8867pyranoindoleBischler–Möhlau reactionNenitzescu reactionPechmann condensationStokes shiftLippert-Mataga equation |
| spellingShingle | Ainur D. Sharapov Ramil F. Fatykhov Igor A. Khalymbadzha Maria I. Valieva Igor L. Nikonov Olga S. Taniya Dmitry S. Kopchuk Grigory V. Zyryanov Anastasya P. Potapova Alexander S. Novikov Vladimir V. Sharutin Oleg N. Chupakhin Fluorescent Pyranoindole Congeners: Synthesis and Photophysical Properties of Pyrano[3,2-<i>f</i>], [2,3-<i>g</i>], [2,3-<i>f</i>], and [2,3-<i>e</i>]Indoles Molecules pyranoindole Bischler–Möhlau reaction Nenitzescu reaction Pechmann condensation Stokes shift Lippert-Mataga equation |
| title | Fluorescent Pyranoindole Congeners: Synthesis and Photophysical Properties of Pyrano[3,2-<i>f</i>], [2,3-<i>g</i>], [2,3-<i>f</i>], and [2,3-<i>e</i>]Indoles |
| title_full | Fluorescent Pyranoindole Congeners: Synthesis and Photophysical Properties of Pyrano[3,2-<i>f</i>], [2,3-<i>g</i>], [2,3-<i>f</i>], and [2,3-<i>e</i>]Indoles |
| title_fullStr | Fluorescent Pyranoindole Congeners: Synthesis and Photophysical Properties of Pyrano[3,2-<i>f</i>], [2,3-<i>g</i>], [2,3-<i>f</i>], and [2,3-<i>e</i>]Indoles |
| title_full_unstemmed | Fluorescent Pyranoindole Congeners: Synthesis and Photophysical Properties of Pyrano[3,2-<i>f</i>], [2,3-<i>g</i>], [2,3-<i>f</i>], and [2,3-<i>e</i>]Indoles |
| title_short | Fluorescent Pyranoindole Congeners: Synthesis and Photophysical Properties of Pyrano[3,2-<i>f</i>], [2,3-<i>g</i>], [2,3-<i>f</i>], and [2,3-<i>e</i>]Indoles |
| title_sort | fluorescent pyranoindole congeners synthesis and photophysical properties of pyrano 3 2 i f i 2 3 i g i 2 3 i f i and 2 3 i e i indoles |
| topic | pyranoindole Bischler–Möhlau reaction Nenitzescu reaction Pechmann condensation Stokes shift Lippert-Mataga equation |
| url | https://www.mdpi.com/1420-3049/27/24/8867 |
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