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

J Org Chem. 2018 Feb 2;83(3):1095-1105. doi: 10.1021/acs.joc.7b02239. Epub 2018 Jan 17.

Abstract

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.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.