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

• Published in: Journal of organic chemistry Vol. 83; no. 3; pp. 1095 - 1105
• Main Authors: Potopnyk, Mykhaylo A, Lytvyn, Roman, Danyliv, Yan, Ceborska, Magdalena, Bezvikonnyi, Oleksandr, Volyniuk, Dmytro, Gražulevičius, Juozas Vidas
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 02.02.2018; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; BORON COMPLEXES; BODIPY DYES; 2-(2'-HYDROXYPHENYL)BENZOXAZOLE; SUBSTITUENT; FACILE SYNTHESIS; FLUORESCENCE; AGGREGATION-INDUCED EMISSION; ENHANCEMENT; STATE; ABSORPTION
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/acs.joc.7b02239

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.