Journal
JOURNAL OF THE ELECTROCHEMICAL SOCIETY
Volume 168, Issue 3, Pages -Publisher
ELECTROCHEMICAL SOC INC
DOI: 10.1149/1945-7111/abedc5
Keywords
Benzothiadiazole; conjugated polymers; electropolymerization; Stille reaction
Funding
- 2232 International Fellowship for Outstanding Researchers Program of TUBITAK [118C251]
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Four novel benzo[c][1,2,5]thiadiazole monomers were designed and successfully synthesized via Stille polycondensation, followed by electropolymerization to form corresponding polymers. The electrochemical and spectroelectrochemical properties of the polymers were carefully characterized, with theoretical calculations revealing the HOMO and LUMO energy levels as well as the electronic band gaps of the polymers.
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 H-1 and C-13 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.
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