Synthesis and electropolymerization of thieno[3,4-c]pyrrole-4,6-dione based donor-acceptor-donor type monomers

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 and PSTPS) were investigated. The results were also compared to their thiophene analogues 5-(2- ethylhexyl)-1,3-di (thiophen-2-yl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione (TTPT) as the monomer and PTTPT as the polymer. Three monomers exhibited dual absorption bands one at high energy region due to the pi-pi* transition and the other one at low energy region which might be attributed to intramolecular charge transfer (ICT). An increase in ICT and a decrease both in the band gap and quantum yield was observed with increasing size of the heteroatomof the donor units. The oxidation potentials of the monomers and that of their corresponding polymer films were found to follow the order of decreasing aromatization energy from thiophene to furan (i.e thiophene > selenophene > furan). Also, heavy-atom substitution (PSTPS) effect showed itself by narrowing the optical band gap of the neutral state electrochromic polymer films: 1.90 eV for PFTPF, 1.82 eV for PTTPT and 1.76 eV for PSTPS.


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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 characteri...
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 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...
Synthesis and mesophase properties of block and random co-polymers of electroactive and liquid crystalline monomers
Yilmaz, F; Kasapoglu, F; Hepuzer, Y; Yagci, Y; Toppare, Levent Kamil; Fernandes, EG; Galli, G (Informa UK Limited, 2005-01-01)
Homo-polymers and random co-polymers of electroactive and liquid crystalline monomers, namely 3-thienylmethyl methacrylate (MTM) and 6-(4-cyanobiphenyl-4'-oxy)hexyl acrylate (LC6), were prepared by conventional free radical polymerization. Block co-polymers of MTM and LC6 were also synthesized by using the 1,1-diphenylethene (DPE) method. The obtained random and block co-polymers exhibited liquid crystal behavior depending on the content of the LC6 units. It was found that microphase separation of the polym...
Citation Formats
D. Çakal and A. M. Önal, “Synthesis and electropolymerization of thieno[3,4-c]pyrrole-4,6-dione based donor-acceptor-donor type monomers,” JOURNAL OF ELECTROANALYTICAL CHEMISTRY, pp. 0–0, 2020, Accessed: 00, 2020. [Online]. Available: