Synthesis and Characterization of Thiophene and Thieno[3,2-b]thiophene Containing Conjugated Polymers

2015-01-01
Rustamh, Elvin
Goker, Seza
UDUM, YASEMİN
Udum, Yasemin Arslan
Toppare, Levent Kamil
Herein, we report the synthesis of two donor-acceptor-donor polymers (P1 and P2) based on thiophene (M1) and thieno [3,2-b]thiophene (M2) as the donor and 2,5-bis(dodecyloxy)benzene as the acceptor unit. The effects of different donor units on the polymers' electrochemical and optical properties were examined by cyclic voltammetry and spectroelectrochemical analysis. Introducing thieno[3,2-b]thiophene unit as the donor unit enhances pi-stacking and consequently lowering the bandgap of the resulting polymer. The electronic band gaps, defined as the onset of the pi-pi transition, were found to be 2.0 eV for P1 and 1.7 eV for P2. Both P1 and P2 films revealed multi-colored electrochromism. A dual-type complementary colored electrochromic device (ECD) using P2/PEDOT in sandwich configuration was constructed. Spectroelectrochemistry, switching ability and open circuit memory of the ECD were investigated. (C) 2015 The Electrochemical Society. All rights reserved.
JOURNAL OF THE ELECTROCHEMICAL SOCIETY

Suggestions

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 of New Thienylene Pyrrole Monomers and Their Electropolymerizations
Eken, Serap; Carbas, Buket Bezgin; Akdağ, Akın; Önal, Ahmet Muhtar (The Electrochemical Society, 2014-01-01)
In this study, four new 2,5-dithienylpyrroles (SNS) 1-(3-fluoro-phenyl)-2,5-di(thiophen-2-yl)-1H-pyrrole (m-FPTP), 1-(3-chlorophenyl)-2,5-di(thiophen-2-yl)-1H-pyrrole (m-ClPTP), 1-(3-bromo-phenyl)-2,5-di(thiophen-2-yl)-1H-pyrrole (m-BrPTP) and 1-(4-bromo-phenyl)-2,5-di(thiophen-2-yl)-1H-pyrrole (p-BrPTP) containing meta and para substituted benzene ring at the nitrogen atom were synthesized via Paal-Knorr condensation of 1,4-di(2-thienyl)-1,4-butanedione with corresponding halo-substituted anilines. The mon...
Synthesis and Electrochemical Polymerization of Dithienosilole-Based Monomers Bearing Different Donor Units
Eken, S.; Ergun, E. G. Cansu; Önal, Ahmet Muhtar (The Electrochemical Society, 2016-01-01)
Three new donor-acceptor-donor (DAD) type monomers containing five membered heteroaromatic rings as the donor units and the silicon-bridged bithiophene as the acceptor unit were synthesized via Stille cross-coupling reaction. The monomers, 2,6-di(furan-2-yl)-4,4-dioctyl-4H-silolo[3,2-b:4,5-b'] dithiophene (FSiF), 4,4-dioctyl-2,6-di(thiophen-2-yl)-4H-silolo[3,2-b:4,5-b']dithiophene (TSiT) and 4,4-dioctyl-2,6-di(selenophen-2-yl)-4H-silolo[3,2-b:4,5-b'] dithiophene (SeSiSe) were polymerized electrochemically v...
Syntheses and Characterization of Benzotriazole, Thienopyrroledione, and Benzodithiophene Containing Conjugated Random Terpolymers for Organic Solar Cells
Goksu, Kardelen; Hizalan, Gonul; Udum, Yasemin Arslan; Hacioglu, Serife Ozdemir; Cevher, Sevki Can; Akrema, Akrema; Toppare, Levent Kamil; Çırpan, Ali (The Electrochemical Society, 2019-11-20)
Two random terpolymers bearing alkoxy-benzodithiophene as an electron-rich unit and N-octylthieno[3,4,c]pyrrole-4,6-dione (TPD) as an electron deficient group with thiophene and selenophene pi bridges, were synthesized and characterized. Electrochemical, optical properties of the polymers were analyzed to get an insight on the effect of different p bridges. Photovoltaic performances of the polymers were investigated with a conventional device architecture. PBTS, PBTSe based polymer solar cells (PSCs) exhibi...
Electrochemical Behavior of Hydrazine Borane in Methanol Solution
Ozhava, Derya; Önal, Ahmet Muhtar; Özkar, Saim (The Electrochemical Society, 2014-01-01)
Electrochemical behavior of hydrazine borane (HB) was investigated on gold electrode in 0.5 M LiClO4 solution in methanol using cyclic voltammetry, electrochemical impedance spectroscopy (EIS) and chronoamperometry. Two irreversible peaks at 164 and 530 mV are attributed to direct electro-oxidation of HB on gold electrode in methanol. Both EIS results and CV data at different scan rates indicate a diffusion controlled electron transfer reaction. Furthermore, the Tafel slope (b = 0.191 V) and charge transfer...
Citation Formats
E. Rustamh, S. Goker, Y. UDUM, Y. A. Udum, and L. K. Toppare, “Synthesis and Characterization of Thiophene and Thieno[3,2-b]thiophene Containing Conjugated Polymers,” JOURNAL OF THE ELECTROCHEMICAL SOCIETY, pp. 0–0, 2015, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/34583.