New electroactive asymmetrical chalcones and therefrom derived 2-amino- / 2-(1H-pyrrol-1-yl)pyrimidines, containing an N-[ω-(4-methoxyphenoxy)alkyl]carbazole fragment: synthesis, optical and electrochemical properties
In this paper we present a synthetic approach to six new D–π–A–D conjugated chromophores containing the N-[ω-(4-methoxyphenoxy)alkyl]carbazole fragment. Such readily functionalizable heterocycle as carbazole was used as a main starting compound for their preparation. The investigation of the optical...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2017-08-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.13.158 |
| _version_ | 1818415742668767232 |
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| author | Daria G. Selivanova Alexei A. Gorbunov Olga A. Mayorova Alexander N. Vasyanin Igor V. Lunegov Elena V. Shklyaeva Georgii G. Abashev |
| author_facet | Daria G. Selivanova Alexei A. Gorbunov Olga A. Mayorova Alexander N. Vasyanin Igor V. Lunegov Elena V. Shklyaeva Georgii G. Abashev |
| author_sort | Daria G. Selivanova |
| collection | DOAJ |
| description | In this paper we present a synthetic approach to six new D–π–A–D conjugated chromophores containing the N-[ω-(4-methoxyphenoxy)alkyl]carbazole fragment. Such readily functionalizable heterocycle as carbazole was used as a main starting compound for their preparation. The investigation of the optical properties has shown that the positive solvatochromism is inherent to the chromophores containing an electron-withdrawing prop-2-en-1-one fragment, while the compounds containing a 2-aminopyrimidine moiety exhibit both positive and negative solvatochromism. The fluorescence quantum yields were experimentally determined for some of the synthesized chromophores; e.g., 1-(5-arylthiophen-2-yl)ethanones quantum yields were found to lie in an interval of 60–80%. Electrochemical oxidation of the synthesized chromophores has resulted in the formation of colored thin oligomeric films that became possible due to the presence of carbazole or pyrrole fragments with free electron-rich positions. |
| first_indexed | 2024-12-14T11:39:50Z |
| format | Article |
| id | doaj.art-607a8a08713044aaa3abd5fce6059ddc |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-14T11:39:50Z |
| publishDate | 2017-08-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-607a8a08713044aaa3abd5fce6059ddc2022-12-21T23:02:53ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972017-08-011311583159510.3762/bjoc.13.1581860-5397-13-158New electroactive asymmetrical chalcones and therefrom derived 2-amino- / 2-(1H-pyrrol-1-yl)pyrimidines, containing an N-[ω-(4-methoxyphenoxy)alkyl]carbazole fragment: synthesis, optical and electrochemical propertiesDaria G. Selivanova0Alexei A. Gorbunov1Olga A. Mayorova2Alexander N. Vasyanin3Igor V. Lunegov4Elena V. Shklyaeva5Georgii G. Abashev6Laboratory of Active Reagents Synthesis, Institute of Technical Chemistry, Russian Academy of Sciences, Ural Division, Academician Korolev street, 3, 614990, Perm, RussiaLaboratory of Active Reagents Synthesis, Institute of Technical Chemistry, Russian Academy of Sciences, Ural Division, Academician Korolev street, 3, 614990, Perm, RussiaLaboratory of Active Reagents Synthesis, Institute of Technical Chemistry, Russian Academy of Sciences, Ural Division, Academician Korolev street, 3, 614990, Perm, RussiaDepartment of Analytical Chemistry, Perm State University, Bukirev street, 15, 614990, Perm, RussiaDepartment of Physics, Radio Electronics and Information Security, Perm State University, Bukirev Street, 15, 614990, Perm, RussiaDepartment of Organic Chemistry, Perm State University, Bukirev street, 15, 614990, Perm, RussiaLaboratory of Active Reagents Synthesis, Institute of Technical Chemistry, Russian Academy of Sciences, Ural Division, Academician Korolev street, 3, 614990, Perm, RussiaIn this paper we present a synthetic approach to six new D–π–A–D conjugated chromophores containing the N-[ω-(4-methoxyphenoxy)alkyl]carbazole fragment. Such readily functionalizable heterocycle as carbazole was used as a main starting compound for their preparation. The investigation of the optical properties has shown that the positive solvatochromism is inherent to the chromophores containing an electron-withdrawing prop-2-en-1-one fragment, while the compounds containing a 2-aminopyrimidine moiety exhibit both positive and negative solvatochromism. The fluorescence quantum yields were experimentally determined for some of the synthesized chromophores; e.g., 1-(5-arylthiophen-2-yl)ethanones quantum yields were found to lie in an interval of 60–80%. Electrochemical oxidation of the synthesized chromophores has resulted in the formation of colored thin oligomeric films that became possible due to the presence of carbazole or pyrrole fragments with free electron-rich positions.https://doi.org/10.3762/bjoc.13.158carbazolechalconeelectrochemical oxidationpyrimidinesolvatochromism |
| spellingShingle | Daria G. Selivanova Alexei A. Gorbunov Olga A. Mayorova Alexander N. Vasyanin Igor V. Lunegov Elena V. Shklyaeva Georgii G. Abashev New electroactive asymmetrical chalcones and therefrom derived 2-amino- / 2-(1H-pyrrol-1-yl)pyrimidines, containing an N-[ω-(4-methoxyphenoxy)alkyl]carbazole fragment: synthesis, optical and electrochemical properties Beilstein Journal of Organic Chemistry carbazole chalcone electrochemical oxidation pyrimidine solvatochromism |
| title | New electroactive asymmetrical chalcones and therefrom derived 2-amino- / 2-(1H-pyrrol-1-yl)pyrimidines, containing an N-[ω-(4-methoxyphenoxy)alkyl]carbazole fragment: synthesis, optical and electrochemical properties |
| title_full | New electroactive asymmetrical chalcones and therefrom derived 2-amino- / 2-(1H-pyrrol-1-yl)pyrimidines, containing an N-[ω-(4-methoxyphenoxy)alkyl]carbazole fragment: synthesis, optical and electrochemical properties |
| title_fullStr | New electroactive asymmetrical chalcones and therefrom derived 2-amino- / 2-(1H-pyrrol-1-yl)pyrimidines, containing an N-[ω-(4-methoxyphenoxy)alkyl]carbazole fragment: synthesis, optical and electrochemical properties |
| title_full_unstemmed | New electroactive asymmetrical chalcones and therefrom derived 2-amino- / 2-(1H-pyrrol-1-yl)pyrimidines, containing an N-[ω-(4-methoxyphenoxy)alkyl]carbazole fragment: synthesis, optical and electrochemical properties |
| title_short | New electroactive asymmetrical chalcones and therefrom derived 2-amino- / 2-(1H-pyrrol-1-yl)pyrimidines, containing an N-[ω-(4-methoxyphenoxy)alkyl]carbazole fragment: synthesis, optical and electrochemical properties |
| title_sort | new electroactive asymmetrical chalcones and therefrom derived 2 amino 2 1h pyrrol 1 yl pyrimidines containing an n ω 4 methoxyphenoxy alkyl carbazole fragment synthesis optical and electrochemical properties |
| topic | carbazole chalcone electrochemical oxidation pyrimidine solvatochromism |
| url | https://doi.org/10.3762/bjoc.13.158 |
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