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

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2021-03-01
Zeytun Karaman, Cansu
Göker, Seza
Özdemir Hacıoğlu, Şerife
Hacıefendioğlu, Tuğba
Yıldırım, Erol
Toppare, Levent Kamil
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 polycondensationreaction. The structural characterizations of the monomers were performed by 1H and 13C NMR spectroscopy and HighResolution Mass Spectroscopy (HRMS). The monomers were then electropolymerized in a three electrode cell system via cyclicvoltammetry. 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 thepolymers, 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, andPTTBTTT, respectively.
Citation Formats
C. Zeytun Karaman, S. Göker, Ş. Özdemir Hacıoğlu, T. Hacıefendioğlu, E. Yıldırım, and L. K. Toppare, “Altering Electronic and Optical Properties of Novel Benzothiadiazole Comprising Homopolymers via π Bridges,” pp. 1–13, 2021, Accessed: 00, 2021. [Online]. Available: https://hdl.handle.net/11511/89417.