Conjugates of 8-[2,2’-bipyridinyl]coumarins as potential chemosensors for Al3+, Cu2+, Cd2+, Zn2+ ions: synthesis and photophysical properties
In this work, we report the synthesis of novel coumarin-bipyridine conjugates using a sequence of C–C coupling reaction between 5,7-dimethoxycoumarins and 3-pyridyl-6-aryl-1,2,4-triazines followed by the Boger reaction with norbornandiene to obtain 8-[2,2'-bipyridyl]-5,7-dimethoxycoumarins. Pho...
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Ural Federal University
2023-12-01
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| Series: | Chimica Techno Acta |
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| Online Access: | https://chimicatechnoacta.ru/article/view/7220 |
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| author | Ainur D. Sharapov Ramil F. Fatykhov Igor A. Khalymbadzha Dmitry S. Kopchuk Igor L. Nikonov Anastasiya P. Potapova Yaroslav K. Shtaitz Pavel A. Slepukhin |
| author_facet | Ainur D. Sharapov Ramil F. Fatykhov Igor A. Khalymbadzha Dmitry S. Kopchuk Igor L. Nikonov Anastasiya P. Potapova Yaroslav K. Shtaitz Pavel A. Slepukhin |
| author_sort | Ainur D. Sharapov |
| collection | DOAJ |
| description | In this work, we report the synthesis of novel coumarin-bipyridine conjugates using a sequence of C–C coupling reaction between 5,7-dimethoxycoumarins and 3-pyridyl-6-aryl-1,2,4-triazines followed by the Boger reaction with norbornandiene to obtain 8-[2,2'-bipyridyl]-5,7-dimethoxycoumarins. Photophysical properties were investigated for the obtained series of 8-[2,2'-bipyridyl]-5,7-dimethoxycoumarins: absorption and emission wavelength maxima are in the region of 212–296 and 401–410 nm, respectively; Stokes shifts are up to 116 nm, and fluorescence quantum yields are up to 15.0%. It was found that titrating the conjugates with Al3+, Zn2+, and Cd2+ ions results in an increase in the intensity of the emission maxima of the complexes, while the opposite effect was observed in the case of titration with Cu2+ ions. These findings suggest that the studied compounds may be considered as promising chemosensing materials. Finally, a positive solvatochromism of 8-[2,2'-bipyridyl]coumarins and their metal complexes was established. The experimental data are supported by mathematical calculations according to the Lippert-Mataga equation and Kosower diagram. |
| format | Article |
| id | doaj-art-55b0331cf90c4c8d83fa43010d2e7b77 |
| institution | DOAJ |
| issn | 2411-1414 |
| language | English |
| publishDate | 2023-12-01 |
| publisher | Ural Federal University |
| record_format | Article |
| series | Chimica Techno Acta |
| spelling | doaj-art-55b0331cf90c4c8d83fa43010d2e7b772025-08-20T03:18:08ZengUral Federal UniversityChimica Techno Acta2411-14142023-12-0110410.15826/chimtech.2023.10.4.175163Conjugates of 8-[2,2’-bipyridinyl]coumarins as potential chemosensors for Al3+, Cu2+, Cd2+, Zn2+ ions: synthesis and photophysical propertiesAinur D. Sharapov0Ramil F. Fatykhov1Igor A. Khalymbadzha2Dmitry S. Kopchuk3Igor L. Nikonov4Anastasiya P. Potapova5Yaroslav K. Shtaitz6Pavel A. Slepukhin7Ural Federal UniversityUral Federal UniversityUral Federal UniversityUral Federal University, I.Ya. Postovsky Institute of Organic Synthesis of UB RASUral Federal University, I.Ya. Postovsky Institute of Organic Synthesis of UB RAS, Ural State Forest Engineering UniversityUral Federal UniversityUral Federal UniversityUral Federal University, I.Ya. Postovsky Institute of Organic Synthesis of UB RASIn this work, we report the synthesis of novel coumarin-bipyridine conjugates using a sequence of C–C coupling reaction between 5,7-dimethoxycoumarins and 3-pyridyl-6-aryl-1,2,4-triazines followed by the Boger reaction with norbornandiene to obtain 8-[2,2'-bipyridyl]-5,7-dimethoxycoumarins. Photophysical properties were investigated for the obtained series of 8-[2,2'-bipyridyl]-5,7-dimethoxycoumarins: absorption and emission wavelength maxima are in the region of 212–296 and 401–410 nm, respectively; Stokes shifts are up to 116 nm, and fluorescence quantum yields are up to 15.0%. It was found that titrating the conjugates with Al3+, Zn2+, and Cd2+ ions results in an increase in the intensity of the emission maxima of the complexes, while the opposite effect was observed in the case of titration with Cu2+ ions. These findings suggest that the studied compounds may be considered as promising chemosensing materials. Finally, a positive solvatochromism of 8-[2,2'-bipyridyl]coumarins and their metal complexes was established. The experimental data are supported by mathematical calculations according to the Lippert-Mataga equation and Kosower diagram.https://chimicatechnoacta.ru/article/view/7220chemosensorscoumarins2,2’-bipyridinesphotophysical propertiesmetal complexes |
| spellingShingle | Ainur D. Sharapov Ramil F. Fatykhov Igor A. Khalymbadzha Dmitry S. Kopchuk Igor L. Nikonov Anastasiya P. Potapova Yaroslav K. Shtaitz Pavel A. Slepukhin Conjugates of 8-[2,2’-bipyridinyl]coumarins as potential chemosensors for Al3+, Cu2+, Cd2+, Zn2+ ions: synthesis and photophysical properties Chimica Techno Acta chemosensors coumarins 2,2’-bipyridines photophysical properties metal complexes |
| title | Conjugates of 8-[2,2’-bipyridinyl]coumarins as potential chemosensors for Al3+, Cu2+, Cd2+, Zn2+ ions: synthesis and photophysical properties |
| title_full | Conjugates of 8-[2,2’-bipyridinyl]coumarins as potential chemosensors for Al3+, Cu2+, Cd2+, Zn2+ ions: synthesis and photophysical properties |
| title_fullStr | Conjugates of 8-[2,2’-bipyridinyl]coumarins as potential chemosensors for Al3+, Cu2+, Cd2+, Zn2+ ions: synthesis and photophysical properties |
| title_full_unstemmed | Conjugates of 8-[2,2’-bipyridinyl]coumarins as potential chemosensors for Al3+, Cu2+, Cd2+, Zn2+ ions: synthesis and photophysical properties |
| title_short | Conjugates of 8-[2,2’-bipyridinyl]coumarins as potential chemosensors for Al3+, Cu2+, Cd2+, Zn2+ ions: synthesis and photophysical properties |
| title_sort | conjugates of 8 2 2 bipyridinyl coumarins as potential chemosensors for al3 cu2 cd2 zn2 ions synthesis and photophysical properties |
| topic | chemosensors coumarins 2,2’-bipyridines photophysical properties metal complexes |
| url | https://chimicatechnoacta.ru/article/view/7220 |
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