Department of Chemistry
A novel asymmetric indolo[3,2-b]carbazole derivative containing benzothiazole and dimesitylboron units: Synthesis, photophysical and sensing properties
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 tetrabutylammonium fluoride (Bu4N+F-) to form an adduct of (Bu4N)+(BDDICZ·F)-. 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. © 2013 Elsevier B.V. All rights reserved.
Benzothiazole, Dimesitylboron, Donor-π-acceptor, Indolo[3, 2-b]carbazole, Photophysical properties, Sensing properties
Source Publication Title
Shi, Heping, Jinwei Yang, Xiuqing Dong, Li Fang, Chuan Dong, and Martin M.F. Choi. "A novel asymmetric indolo[3,2-b]carbazole derivative containing benzothiazole and dimesitylboron units: Synthesis, photophysical and sensing properties." Synthetic Metals 179 (2013): 42-48.