Selenophene as a Bridge in Molecular Architecture of Benzotriazole Containing Conjugated Copolymers to Gain Insight on Optical and Electrochemical Properties of Polymers

Abstract

Polymers containing selenophene as a π bridge; poly(2-(2-octyldodecyl)-4-(selenophen-2-yl)-7-(5-(thiophen-2-yl)selenophen-2-yl)-2H-benzo[d][1,2,3]triazole) (P1) and poly(2-(2-Downloaded by [FU Berlin] at 18:45 25 June 2015 ACCEPTED MANUSCRIPT ACCEPTED MANUSCRIPT 2 octyldodecyl)-4-(5-phenylselenophen-2-yl)-7-(selenophen-2-yl)-2H-benzo[d][1,2,3]triazole (P2) were synthesized via Stille and Suzuki coupling reactions respectively. Optical and electrochemical properties were investigated and comparisons with their thiophene analogs were done. Selenophene substitution resulted in low band gap and red shifted absorption, fast switching times (less than 1s) with reasonable optical contrast. Switching time of P2 was 0.2 second which is the fastest switching time regarding benzotriazole-based polymers. Photovoltaic properties of P1 and P2 were investigated. The optimized devices showed 0.45% and 0.75% power conversion efficiency, respectively.

From Narrow to Narrower: A Very Low Band Gap [1,2,5]thiadiazolo[3,4-g]quinoxaline-Based Donor-Acceptor-Donor Type Electrochromic Polymer

“…The monomer 1 was polymerized and characterized in 0.1 M TBAH dissolved CH 2 Cl 2 . After polymerization and before characterization, the corresponding polymer P1 coating on the working electrode surface was washed with CH 2 Cl 2 , and to break in the polymer film, its redox state was switched a number of times 32 and tributyl(selenophen-2-yl)stannane 16 were carried out according to accepted procedures found in the literature. The spectral data were well in agreement with those reported previously for these compounds.…”

“…There have been few studies on D-A-D based polyselenophenes. 7,[14][15][16] 2,1,3-Benzothiadiazole [17][18][19][20][21] and quinoxaline [22][23][24][25][26][27] groups are widely used in the synthesis of the D-A-D type polymers since z E-mail: mozkut@yyu.edu.tr; atilla.cihaner@atilim.edu.tr they have a strong electron withdrawing capacity, resulting in narrow bandgap polymers. It has been observed that quinoxaline-fused thiadiazoles have priority over single thiadiazole or quinoxaline groups based on their electron withdrawing capacity.…”