N,O π-Conjugated 4‑Substituted 1,3-Thiazole BF2 Complexes: Synthesis and Photophysical Properties

A series of 1,3-thiazole-based organoboron complexes has been designed and synthesized by acylation of 2-amino 4-subsituted 1,3-thiazoles with (4-dimethylamino)­benzoyl chloride and the subsequent BF2 complexation reaction. The influence of substituents in position 4 of the thiazole ring on photophy...

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Bibliographic Details
Published in:Journal of organic chemistry 2018-02, Vol.83 (3), p.1095-1105
Main Authors: Potopnyk, Mykhaylo A, Lytvyn, Roman, Danyliv, Yan, Ceborska, Magdalena, Bezvikonnyi, Oleksandr, Volyniuk, Dmytro, Gražulevičius, Juozas Vidas
Format: Article
Language:English
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Summary:A series of 1,3-thiazole-based organoboron complexes has been designed and synthesized by acylation of 2-amino 4-subsituted 1,3-thiazoles with (4-dimethylamino)­benzoyl chloride and the subsequent BF2 complexation reaction. The influence of substituents in position 4 of the thiazole ring on photophysical properties of the complexes has been investigated. Synthesized thiazolo­[3,2-c]­[1,3,5,2]­oxadiazaborinines mainly showed intensive fluorescence in solutions. Complex with a 4,5-unsubstituted thiazole unit demonstrated an aggregation induced emission (AIE) effect and a very high fluorescent quantum yield (94%) in the solid state because of the inhibition of π–π/π–n interactions in the molecular packing.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b02239