Synthesis and polymerization of 2-and 3-substituted thiophene derivatives linked by polyether bridges

New compounds consisting of 2- and 3-thienyl units linked by polyether bridges have been synthesized and their electrochemical polymerization was performed via constant potential electrolysis (CPE) in an electrolytic solution containing 0.1 M tetrabutylammonium hexafluorophosphate (TBAPF(6)) dissolved in CH3CN. 2-Thienyl monomers (I and II), but not 3-thienyl monomers (III and IV), were also polymerized via chemical oxidation, which yielded broken pi-conjugated polymer products. The polymers were characterized using H-1 NMR and FT-IR spectroscopic techniques. It was found that both chemical and electrochemical oxidation of 2-thienyl monomers gave mainly poly(2,2'-bithiophenemethylene) due to elimination of polyether chains during the polymerization reaction. On the other hand, electrochemical oxidation of 3-thienyl monomers resulted in corresponding polymers without any cleavage of polyether bridges. Spectroelectrochemical (SPEL) properties of the products were investigated using UV-Vis spectroscopic techniques.


Synthesis, characterization and optoelectrochemical properties of poly(1,6-bis(2,5-di(thiophen-2-yl)-1H-pyrrol-1-yl)hexane) and its copolymer with EDOT
Ak, Metin; Sahmetlioglu, Ertugrul; Toppare, Levent Kamil (Elsevier BV, 2008-09-01)
A new polythiophene derivative was synthesized by electrochemical oxidative polymerization of 1,6-bis(2,5-di(thiophen-2-yl)-1H-pyrrol-1-yl)hexane (TPH). The structure of the monomer was elucidated by H-1, C-13, MR and mass analyses. The polymer P(TPH) and its copolymer with 3,4-ethylenedioxythiophene (P(TPH-co-EDOT)) were synthesized via potentiostatic electrochemical polymerization. Characterizations of the resulting polymers were performed by cyclic voltammetry (CV), FTIR, UV-vis spectroscopies; and condu...
Synthesis and electropolymerization of thieno[3,4-c]pyrrole-4,6-dione based donor-acceptor-donor type monomers
Çakal, Deniz; Önal, Ahmet Muhtar (Elsevier BV, 2020-04-01)
Two monomers containing thieno [3,4-c]pyrrole-4,6-dione (TP) acceptor units, namely 5-(2-ethylhexyl)-1,3-di (furan2-yl)-4H-thieno [3,4-c]pyrrole-4,6(5H)-dione (FTPF) and 5-(2-ethylhexyl)-1,3-di (selenophen-2-yl)-4H-thieno[3,4-c] pyrrole-4,6(5H)-dione (STPS), were synthesized via donor-acceptor-donor approach. Under the same template structure, the effect of heteroatom of the donor unit on redox and optical properties of the monomers and their corresponding polymers obtained via electrochemical method (PFTPF...
Synthesis and spectroelectrochemical characterization of multi-colored novel poly(3,6-dithienylcarbazole) derivatives containing azobenzene and coumarin chromophore units
Yigit, Deniz; Hacioglu, Serife O.; GÜLLÜ, Mustafa; Toppare, Levent Kamil (Elsevier BV, 2016-04-01)
Azobenzene and coumarin units bearing four novel 3,6-linked thiophene-carbazole-thiophene type electroactive monomers were synthesized in order to observe the effects of strong chromophore units on the electrochemical and spectroelectrochemical behaviors of resulting pi-conjugated conducting polymers (PTCbzAz, PECbzAz, PTCbzCo and PECbzCo). Electronic and optoelectronic properties of all polymers were investigated by cyclic voltammetry and in situ spectroelectrochemical studies, and their oxidation potentia...
Conducting copolymers of thiophene functionalized polystyrenes with thiophene
Sahin, E; Camurlu, P; Toppare, Levent Kamil; Mercore, VM; Cianga, I; Yagci, Y (Elsevier BV, 2005-06-01)
Thiophene capped polystyrenes (TCP1, TCP2) were synthesized by atom transfer radical polymerization of styrene followed by Suzuki condensation with 2-thiophene boronic acid. Electrically conducting graft polymers of TCP1 and TCP2 with thiophene were achieved by electrochemical methods. Characterization of the graft polymers were performed by cyclic voltammetry (CV), Fourier transform infrared spectroscopy, differential scanning calorimetry, scanning electron microscopy analyses. Electrochromic properties of...
Electrochemical copolymerization and characterization of dianilines linked by polyether bridge with aniline
TİRKEŞ, SEHA; Önal, Ahmet Muhtar (Springer Science and Business Media LLC, 2010-04-01)
Copolymer of aniline and triethylene glycol bis(o-aminophenyl) ether was synthesized by constant potential electrolysis. Cyclic voltammogram of the copolymer films recorded in the monomer-free electrolytic solution revealed that the redox behavior of the films approaches to that of poly(triethylene glycol bis(o-aminophenyl) ether) with increasing amount of triethylene glycol bis(o-aminophenyl) in the feed ratio. Copolymerization was investigated by in situ recording the changes in the electronic absorption ...
Citation Formats
S. Tirkeş and A. M. Önal, “Synthesis and polymerization of 2-and 3-substituted thiophene derivatives linked by polyether bridges,” JOURNAL OF ELECTROANALYTICAL CHEMISTRY, pp. 189–196, 2004, Accessed: 00, 2020. [Online]. Available: