Effect of furan, thiophene and selenophene donor groups on benzoselenadiazole based donor-acceptor-donor systems

Abstract

A series of the monomers called 4,7-di(furan-2-yl)benzo[c][1,2,5]selenadiazole (OSeO), 4,7-di(thiophen-2-yl)benzo[c][1,2,5]selenadiazole (SSeS) and 4,7-di(selenophen-2-yl)benzo[c][1,2,5]selenadiazole (SeSeSe) was synthesized via a donor–acceptor–donor (D-A-D) approach. Benzoselenadiazole was used as an acceptor unit and furan, thiophene and selenophene were used as donor units. The effects of chalcogen atoms (O, S, and Se) in furan, thiophene and selenophene were investigated systematically on the properties of the monomers and their corresponding polymers (POSeO, PSSeS and PSeSeSe, respectively), which were polymerized electrochemically via potentiodynamic or potentiostatic methods. The monomers OSeO, SSeS and SeSeSe exhibited low oxidation potentials of 1.15, 1.25 and 1.19V vs. Ag/AgCl, respectively. Intramolecular charge transfer interaction between donor and acceptor units was demonstrated from the emission spectra of the monomers. Also, the optical studies showed that the ambipolar and electrochromic polymers POSeO, PSSeS and PSeSeSe have low band gaps of 1.57, 1.47 and 1.45eV, respectively.