Altering Electronic and Optical Properties of Novel Benzothiadiazole Comprising Homopolymers via π Bridges


Karaman C., Goeker S., Hacioglu Ş., Haciefendioglu T., YILDIRIM E., TOPPARE L. K.

Journal of the Electrochemical Society, vol.168, no.3, 2021 (Peer-Reviewed Journal) identifier identifier

  • Publication Type: Article / Article
  • Volume: 168 Issue: 3
  • Publication Date: 2021
  • Doi Number: 10.1149/1945-7111/abedc5
  • Journal Name: Journal of the Electrochemical Society
  • Journal Indexes: Science Citation Index Expanded, Scopus, Analytical Abstracts, Applied Science & Technology Source, Chemical Abstracts Core, Chimica, Compendex, Computer & Applied Sciences, INSPEC
  • Keywords: Benzothiadiazole, conjugated polymers, electropolymerization, Stille reaction, CONJUGATED POLYMERS, BAND-GAP, CHARGE-TRANSFER, THIOPHENE, FURAN, CHAIN, PERFORMANCE, COPOLYMERS, PROGRESS, CELLS

Abstract

© 2021 The Electrochemical Society ("ECS"). Published on behalf of ECS by IOP Publishing Limited.Four novel benzo[c][1,2,5]thiadiazole comprising monomers namely 5-fluoro-6-((2-octyldodecyl)oxy)-4,7-di(thiophen-2-yl)benzo[c][1,2,5]thiadiazole (TBTT), 5-fluoro-4,7-bis(4-hexylthiophen-2-yl)-6-((2-octyldodecyl)oxy)benzo[c][1,2,5]thiadiazole (HTBTHT), 5-fluoro-4,7-di(furan-2-yl)-6-((2-octyldodecyl)oxy)benzo- [c][1,2,5]thiadiazole (FBTF), and 5-fluoro-6-((2-octyldodecyl)oxy)-4,7-bis(thieno[3,2-b]thiophen-2-yl)benzo[c][1,2,5]thiadiazole (TTBTTT) were designed, and synthesized successfully via Stille polycondensation reaction. The structural characterizations of the monomers were performed by 1H and 13C NMR spectroscopy and High Resolution Mass Spectroscopy (HRMS). The monomers were then electropolymerized in a three electrode cell system via cyclic voltammetry. The electrochemical, and spectroelectrochemical characterization of the polymers were reported in detail. Besides, theoretical calculations were performed to elucidate observed experimental properties. According to the cyclic voltammogram of the polymers, HOMO and LUMO energy levels were calculated as -5.68 eV/-3.91 eV, -5.71 eV/-3.72 eV, -5.61 eV/-4.04 eV, and -5.51 eV/-3.71 eV and the electronic band gaps were 1.77 eV, 1.99 eV, 1.57 eV, and 1.80 eV for PTBTT, PHTBTHT, PFBTF, and PTTBTTT, respectively.