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

Date

2021-03-01

Author

Zeytun Karaman, Cansu
Goeker, Seza
Hacioglu, Serife O.
Haciefendioglu, Tugba
Yıldırım, Erol
Toppare, Levent Kamil

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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.

URI

https://iopscience.iop.org/article/10.1149/1945-7111/abedc5
https://hdl.handle.net/11511/89537

Journal

JOURNAL OF THE ELECTROCHEMICAL SOCIETY

DOI

https://doi.org/10.1149/1945-7111/abedc5

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Department of Chemistry, Article

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Altering Electronic and Optical Properties of Novel Benzothiadiazole Comprising Homopolymers via π Bridges Zeytun Karaman, Cansu; Göker, Seza; Özdemir Hacıoğlu, Şerife; Hacıefendioğlu, Tuğba; Yıldırım, Erol; Toppare, Levent Kamil (2021-03-01) 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 polyconde...
The impact of [1,2,5]chalcogenazolo[3,4-f]-benzo[1,2,3]triazole structure on the optoelectronic properties of conjugated polymers Alkan, Ecem Aydan; GÖKER, SEZA; Sarigul, Hatice; Yıldırım, Erol; Udum, Yasemin Arslan; Toppare, Levent Kamil (2020-04-01) Two novel conjugated near-infrared (NIR) absorbing donor-acceptor type copolymers comprising benzodithiophene as the donor and [1,2,5]chalcogenazolo[3,4-f]-benzo[1,2,3]triazole derivatives as the acceptors, spaced with thiophene as the pi-bridge, were designed and synthesized via Stille polycondensation reaction. The effect of acceptor strength on optoelectronic properties was targeted and investigated. Branched alkyl chains (the extended 2-octyl-1-dodecyl alkyl chain; -C8C12) were introduced to 5H-[1,2,3]t...
Tuning molecular energy levels and band gap of two-dimensional benzo[1,2-b:4,5-b '] dithiophene and quinoxaline bearing polymers Yasa, Mustafa; Goker, Seza; Udum, Yasemin; Toppare, Levent Kamil (Elsevier BV, 2019-08-15) Two novel donor-acceptor (D-A)-type two-dimensional (2-D) polymers of PBDTSeQ (P1) and PBDTFQ (P2) were synthesized and characterized where 4,8-bis[5-(2-ethylhexyl) thiophen-2-yl] benzo[1,2-b:4,5-b'] dithiophene (BDT) was used as the donor unit. 2,3-Bis(3,4-bis(octyloxy)phenyI)-5,8-dibromoquinoxaline was used as the acceptor moiety and selenophene and furan were utilized as n bridges. Optoelectronic properties of the polymers were examined by electrochemical and spectroelectrochemical characterizations. In ...
Investigation of Fluorine Atom Effect on Benzothiadiazole Acceptor Unit in Donor Acceptor Donor Systems Çakal, Deniz; Akdağ, Akın; Önal, Ahmet Muhtar (The Electrochemical Society, 2019-07-12) Synthesis of two new pi-conjugated monomers containing fluorine substituted benzothiadiazoles as acceptor units and 3,4-ethylenedioxythiophene (EDOT) as donor unit was accomplished by facilitating Stille cross-coupling reactions (4,7-bis(2,3-dihydrothieno[3,4-b][1,4] dioxin-5-yl)-5-fluorobenzo[c][1,2,5] thiadiazole (E2BTD-F) and 4,7-bis(2,3-dihydrothieno [3,4-b][1,4] dioxin-5-yl)-5,6-difluorobenzo[c][1,2,5] thiadiazole (E2BTD-2F)). NMR and HRMS spectra of newly synthesized compounds are in agreement with th...
Synthesis and electro-optical properties of new conjugated hybrid polymers based on furan and fluorene units Gunes, Arzu; CİHANER, ATİLLA; Önal, Ahmet Muhtar (2013-02-01) A novel series of hybrid monomers containing furan and fluorene units, namely 2-(2-(furan-2-yl)-9H-fluoren-7-yl)furan (FFF), 2,7-di(furan-2-yl)-9H-fluoren-9-one (FOF) and 2-(2-(furan-2-yl)-9,9-dihexyl-9H-fluoren-7-yl)furan (FHF), was synthesized and their electrochemical polymerization was achieved via potential cycling. Optical and electrochemical properties of the polymers, poly(2-(2-(furan-2-yl)9H-fluoren-7-yl)furan (PFFF), poly(2,7-di(furan-2-yl)-9H-fluoren-9-one) (PFOF) and poly(2-(2-(furan2-yl)-9,9-di...

Citation Formats

C. Zeytun Karaman, S. Goeker, S. O. Hacioglu, T. Haciefendioglu, E. Yıldırım, and L. K. Toppare, “Altering Electronic and Optical Properties of Novel Benzothiadiazole Comprising Homopolymers via pi Bridges,” JOURNAL OF THE ELECTROCHEMICAL SOCIETY, pp. 0–0, 2021, Accessed: 00, 2021. [Online]. Available: https://iopscience.iop.org/article/10.1149/1945-7111/abedc5.