Synthesis and characterization of a bifunctional amido-thiophene monomer and its copolymer with thiophene and electrochemical properties

A bifunctional amido-thiophene namely hexamethylene (bis-3-thiophene acetamide) (HMTA) was synthesized by the reaction of 3-thiophene acetic acid with hexamethylene diamine. Copolymerization in the presence of thiophene was achieved electrochemically in tetrabutylammonium tetrafluoroborate/acetonitrile (TBAFB/AN). Spectroelectro-chemical analysis of the resulting copolymer [P(HMTA-co-Th)] reflected electronic transitions at 505 nm, 740 nm and similar to 1000 nm, revealing pi to pi* transition, polaron and bipolaron band formation respectively. Switching ability was evaluated by a kinetic study via measuring the transmittance (%T) at the maximum contrast. Dual type polymer electrochromic devices (ECDs) based on P(HMTA-co-Th) and poly(ethylene dioxythiophene) (PEDOT) have been constructed. Spectroelectrochemistry, switching ability and stability of the devices were investigated by UV-vis spectroscopy and cyclic voltammetry. These devices exhibit low switching voltages (between 0.0V and + 1.6V), short switching times with reasonable switching stability under atmospheric conditions.


Synthesis and characterization of thiophen-3-yl-acetic acid 4-pyrrol-1-yl-phenyl ester and its conducting polymers
Bingöl, Bahar; Toppare, Levent Kamil; Department of Chemistry (2003)
Thiophen-3-yl acetic acid 4-pyrrol-1-yl phenyl ester (TAPE) monomer was synthesized by the reaction of thiophene acetic acid with thionyl chloride, and further reaction of thiophen-3-yl-acetyl chloride with 4-pyrrol-1-yl phenol. Electrochemical behavior of this monomer (TAPE) was determined by cyclic voltammetry. Homopolymers were achieved both by using electrochemical and chemical polymerization techniques. Copolymers of TAPE in the presence of bithiophene and pyrrole were synthesized by potentiostatic ele...
A soluble conducting polymer of 4-(2,5-di(thiophen-2-yl)-1H-pyrrol-1-yl)benzenamine and its multichromic copolymer with EDOT
YİLDİZ, Ersin; ÇAMURLU, PINAR; Tanyeli, Cihangir; AKHMEDOV, Idris; Toppare, Levent Kamil (2008-01-15)
Here we report the synthesis of a monomer, 4-(2,5-di(thiophen-2-yl)-1H-pyrrol-1-yl)benzenamine (SNS-NH2) produced by the reaction of 1,4-di(2-thienyl)-1,4-butanedione and benzene-1,4-diamine. This monomer was electrochemically polymerized in the presence of LiClO4, NaClO4 (1:1) as the supporting electrolyte in acetonitrile. Copolymerization in the presence of 3,4-ethylenedioxythiophene (EDOT) was achieved in acetonitrile NaClO4/LiClO4 (0.1 M:0.1 M) solvent-electrolyte couple. Resulting homopolyrner and copo...
Synthesis and electrochromic properties of a symmetric polythiophene derivative: Decanedionic acid bis-(2-thiophene-3-yl-ether)ester and its copolymer with thiophene
Aslan, E; Camurlu, P; Toppare, Levent Kamil (2005-04-01)
Here we describe the electrochemical homopolymerization and copolymerization of decanedionic acid bis-(2-thiophene-3-yl- ether)ester (DATE) in the presence of thiophene. Tetrabutylammonium tetrafluoroborate (TBAFB) was utilized as the supporting electrolyte in acetonitrile (ACN) /borontrifloride ethylether (BFEE) solvent mixture (8:2D, v/v). Electrochemical homopolymerization of DATE and copolymerization with thiophene were studied by cyclic voltammetry (CV). Conducting polymers were characterized by Fourie...
Synthesis of conducting graft copolymers of 2-(N-pyrrolyl)ethylvinyl ether with pyrrole
Bengu, B; Toppare, Levent Kamil; Kalaycioglu, E (2001-01-01)
2-(N-pyrrolyl)ethylvinyl ether (2-NEVE) was synthesized from 2-chloroethylvinyl ether (2-CEVE) via a phase catalysis reaction. Cyclic voltammetric studies were carried out to check for the electroactivity of 2-NEVE. Poly(2-(N-pyrrolyl)ethylvinyl ether) [poly(2-NEVE)] was synthesized via chemical methods. Graft copolymers of pyrrole and 2-NEVE were synthesized by electrochemical methods. The chemical structures of 2-NEVE and poly(2-NEVE) were investigated by several spectroscopic methods. Graft copolymers we...
Synthesis and characterization of a new copolymer of PTSA doped polypyrrole
Levent, A.; Hacaloğlu, Jale; Toppare, Levent Kamil; Yagci, Y. (2003-04-04)
In this work poly(2-methylbutyl 2-(3-thienyl)acetate was prepared by galvanostatic polymerization of (S)-2-methylbutyl 2-(3-thienyl) acetate. Polypyrrole was electrochemically polymerized on a poly(2-methylbutyl 2-(3-thienyl)-acetate) coated anode through the thiophene moities of the matrix polymer. Direct insertion probe pyrolysis MS and Curie point pyrolysis GCMS techniques were utilized for structural and thermal characterizations.
Citation Formats
M. AK, A. Çırpan, F. Yılmaz, Y. YAGCI, and L. K. Toppare, “Synthesis and characterization of a bifunctional amido-thiophene monomer and its copolymer with thiophene and electrochemical properties,” EUROPEAN POLYMER JOURNAL, pp. 967–973, 2005, Accessed: 00, 2020. [Online]. Available: