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

By Karabay, Lutfiye Canan; Karabay, Baris; Karakoy, Merve Serife; Cihaner, Atilla
Published in Journal of Electroanalytical Chemistry NULL 2016

Abstract

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 1.19 V 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 1.45 eV, respectively.

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