Preparation and Characterization of a π-Conjugated Donor-Acceptor System Containing the Strongly Electron-Accepting Tetraphenylborolyl Unit.

A novel thiophene-bridged donor-acceptor system was synthesized with a carbazole as donor and a borole as acceptor unit. The borole group was successfully installed via the tin-boron exchange reaction of 1,1-dimethyl-2,3,4,5-tetraphenylstannole with 9-(5-(dibromoboryl)thiophen-2-yl)carbazole. The effect of the borole on the optoelectronic properties of the donor-acceptor system was explored by spectroscopic (UV/Vis and fluorescence spectroscopy), electrochemical (cyclic voltammetry) and theoretical (TD-DFT) methods as well as by modifying its structure. The corresponding donor-acceptor compound bearing the widely employed dimesitylboryl acceptor group was also synthesized for comparison.