A novel asymmetric indolo[3,2-b]carbazole derivative containing benzothiazole and dimesitylboron units: Synthesis, photophysical and sensing properties

摘要

A novel asymmetric acceptor-π-donor-π-acceptor compound, 2-benzothiazolyl-8-dimesitylboryl-5,11-dihexylindolo[3,2-b]carbazole (BDDICZ), has been successfully synthesized by introducing a benzothiazole (electron-acceptor) moiety and a dimesitylboron (electron-acceptor) group to 2-position and 8-position of indolo[3,2-b]carbazole (an electron-donor), respectively. The structure of BDDICZ was fully characterized by NMR, MS and elemental analysis and was studied by both experimental and theoretical methods. Our results demonstrate that BDDICZ is a sensitive ratiometric fluorescence probe which shows remarkable color change with fluoride ion (F~-). The theoretical calculations confirm that BDDICZ can readily react with tetrabutyl ammonium fluoride (Bu_4N~+F~-) to form an adduct of (Bu_4N)~+(BDDICZF)~-. Moreover, BDDICZ possesses appropriate HOMO and LUMO energy states and a high fluorescence quantum yield, indicating its potential application as an ideal hole-transporting and/or light-emitting material in optoelectronic devices.