Crystals of 4,7-Di-2-thienyl-2,1,3-benzothiadiazole and Its Derivative with Terminal Trimethylsilyl Substituents: Synthesis, Growth, Structure, and Optical-Fluorescent Properties

Postnikov, V.A.; Yurasik, G.A.; Kulishov, A.A.; Sorokin, T.A.; Lyasnikova, M.S.; Sorokina, N.I.; Skorotetcky, M.S.; Popova, V.V.; Levkov, L.L.; Borshchev, O.V.; Svidchenko, E.A.; Surin, N.M.; Ponomarenko, S.A.

Авторы: Postnikov Valery A., Yurasik Georgy A., Kulishov Artem A., Sorokin Timofei A., Lyasnikova Maria S., Sorokina Nataliya I., Skorotetcky Maxim S., Popova Vlada V., Levkov Lev L., Borshchev Oleg V., Svidchenko Evgeniya A., Surin Nikolay M., Ponomarenko Sergey A.
Журнал: Crystals
Том: 13
Номер: 12
Год издания: 2023
Издательство: MDPI
Местоположение издательства: Basel, Switzerland
Первая страница: 1697
Последняя страница: 1697
DOI: 10.3390/cryst13121697
Аннотация: Among short donor–acceptor molecules with a central benzothiadiazole fragment, 4,7-di-2-thienyl-2,1,3-benzothiadiazole (T-BTD) is one of the most well-known compounds, valued for its photophysical and semiconductor properties. We have synthesized a derivative of 4,7-di-2-thienyl-2,1,3-benzothiadiazole with trimethylsilyl end-substituents, 4,7-bis(5-(trimethylsilyl)thiophen-2-yl)benzothiadiazole (TMS-T-BTD). The phase transition parameters and thermal stability of T-BTD and TMS-T-BTD were investigated using DSC and TGA methods. The presence of the trimethylsilyl end-groups in TMS-T-BTD significantly enhances solubility, increases the melting temperature, and improves the resistance of TMS-T-BTD to evaporation in the liquid state. Single crystals of T-BTD and TMS-T-BTD were grown from solutions, with the largest sizes being 7 × 2 × 0.5 mm3 and 8 × 1 × 0.45 mm3, respectively. Using single-crystal X-ray diffraction at 293 K, the crystal structure of T-BTD was refined in the rhombic system (sp.gr. Pcab, Z = 8), while for TMS-T-BTD, it was determined for the first time in the monoclinic system (sp.gr. P21/c, Z = 4). The relationship between observed growth anisotropy and molecular packing in the crystals was analyzed. The results of investigations into the spectral-fluorescent properties of solutions in hexane and THF are presented. The solvatochromic effect was studied in a series of solvents, including hexane, THF, dichloromethane, and acetonitrile. The photostability of the compounds in hexane solutions was examined. It was found that the quantum yield of photodestruction for T-BTD is 13 times higher than that of TMS-T-BTD. The fluorescent properties of T-BTD and TMS-T-BTD crystals were investigated.The research was supported by the Russian Science Foundation grant No. 22-13-00255.
Добавил в систему: Борщев Олег Валентинович

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Crystals of 4,7-Di-2-thienyl-2,1,3-benzothiadiazole and Its Derivative with Terminal Trimethylsilyl Substituents: Synthesis, Growth, Structure, and Optical-Fluorescent Propertiesстатья Исследовательская статья

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