Synthesis, characterization, and electrochromic properties of conducting copolymers of 2-[(3-thienylcarbonyl)oxy]ethyl 3-thiophene carboxylate with thiophene and pyrrole

Date

2004-07-01

Author

Bulut, U
Alkan, S
Yilmaz, F
Yagci, Y
Toppare, Levent Kamil

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

192
views

0
downloads

2-[(3-Thienylcarbonyl)oxy]ethyl 3-thiophene carboxylate (TOET) was synthesized via the reaction of 3-thionylcarboxylic acid with ethylene glycol, and electrochemically polymerized with thiophene (Th) and pyrrole (Py) by using tetrabutylannnonium tetrafluoroborate (TBAFB) as the supporting electrolyte in acetonitrile (ACN). Characterization of the resulting copolymers were performed via cyclic voltammetry, FTIR, and scanning electron microscopy (SEM). Electrical conductivities are measured by the four-probe technique. Spectroelectrochemical analysis shows that the copolymer of this monomer with Th has an electronic band gap (due to the pi-pi* transition) of 1.97 eV. The homopolymer possessed a yellow color in its reduced form, and a greenish blue color in its oxidized form, however, no switching ability. The copolymer exhibited multi-color changes from a pale red in the neutral state, an orange, and finally a bluish-gray upon oxidation, and a long-term switching stability up to 450 double switches.

Subject Keywords

Materials Chemistry, General Chemistry, Polymers and Plastics, Ceramics and Composites

URI

https://hdl.handle.net/11511/47342

Journal

JOURNAL OF MACROMOLECULAR SCIENCE-PURE AND APPLIED CHEMISTRY

DOI

https://doi.org/10.1081/ma-120039180

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

Synthesis, characterization and electrochromic properties of conducting copolymers of 3-[(3-thienylcarbonyl)oxy]-2,2-bis{[(3-thienylcarbonyl)oxy]}propyl 3-thiophene carboxylate with thiophene and pyrrole Bulut, U; Yilmaz, F; Yagci, Y; Toppare, Levent Kamil (Elsevier BV, 2004-01-01) 3-[(3-Thienylcarbonyl)oxy]-2,2-bis{[(3-thienylcarbonyl)oxy]}propyl 3-thiophene carboxylate (TOTPT) was synthesized by the reaction of 3-thionylcarbonyl chloride with pentaerythritol, it was electrochemically polymerized with either thiophene or pyrrole by using tetrabutylammonium tetrafluoroborate (TBAFB) as the supporting electrolyte in acetonitrile (AN). Characterization of the resulting copolymers was carried out by FTIR spectroscopy, cyclic voltammetry, thermal gravimetry analysis (TGA), differential sc...
Synthesis and characterization of conducting graft copolymers based on oligophenols Sahmetlioglu, Ertugrul; Arikan, Ufuk; Toppare, Levent Kamil; Yuruk, Huseyin; Mart, Hasan (Informa UK Limited, 2006-10-01) Oligo-2-aminophenol (OAF) was synthesized with oxidative polycondensation of 2-aminophenol and hydrogen peroxide in an aqueous alkaline medium at 80 degrees C. Oligo-2-aminophenol with thiophene side groups (TOAF) was obtained by the reaction of OAF and thiophene-3-acetic acid. Graft copolymers of TOAF and pyrrole were synthesized by electrochemical polymerization in p-toluene sulfonic acid (PTSA)/water medium. Characterization of the graft copolymer (TOAF-g-Py), was carried out by combination of techniques...
Synthesis and Characterization of Conducting Copolymers of Bisphenol A-Diglycidyl Ether with Thiophene Side-Groups and Pyrrole Sahmetlioglu, Ertugrul; Varol, Ramazan; Toppare, Levent Kamil; Yuruk, Huseyin (Informa UK Limited, 2009-01-01) Copolymers of bisphenol A-diglycidyl ether with thiophene side-groups and pyrrole were synthesized by electrochemical polymerization. Bisphenol A-diglycidyl ether with thiophene side-groups (DGEBATh) was obtained from the reaction between bisphenol A-diglycidyl ether (DGEBA) and thiophene-3-acetic acid. The syntheses of copolymers of DGEBATh and pyrrole were achieved electrochemically using three different supporting electrolytes, p-toluene sulfonic acid (PTSA), sodium dodecyl sulfate (SDS) and tetrabutylam...
Synthesis, characterization and electrochromic properties of copolymer of terephthalic acid bis-(thiophen-3-yl-methyl) thioester with thiophene Turkarslan, O; Erden, A; Sahin, E; Toppare, Levent Kamil (Informa UK Limited, 2006-01-01) Terephthalic acid bis-(thiophen-3-yl-methyl thioester) (TTMT) was synthesized via the reaction of thiophen-3-yl methanethiol with terephthaloyl dichloride. Nuclear magnetic resonance ( H-1-NMR) spectroscopy and Fourier transform infrared (FTIR) spectroscopy were utilized for the characterization of the monomer. Electrochemical copolymerization of TTMT with thiophene in acetonitrile/boron trifluoride diethyl etherate (AN/BFEE) (8:2, v/v) solvent mixture was realized by using tetrabutylammonium tetrafluorobor...
Synthesis and characterization of alternating copolymers of thiophene-containing N-phenyl maleimide and styrene by photoinduced radical polymerization and their use in electropolymerization Yilmaz, F; Cianga, L; Guner, Y; Topppare, L; Yagci, Y (Elsevier BV, 2004-08-05) A novel N-(4-(3-thienyl methylene)-oxycarbonylphenyl) maleimide (MBThi) monomer was synthesized by the esterification reaction of maleimidobenzoic acid (MBA) with 3-thiophene methanol. Photoinduced radical polymerization was employed to prepare the alternating copolymers of MBThi with styrene (St) at room temperature using omega,omega-dimethoxy-omega-phenylacetophenone (DMPA) as photoinitiator. Different copolymerization conditions were examined to estimate the influence of the used solvents and comonomers'...

Citation Formats

U. Bulut, S. Alkan, F. Yilmaz, Y. Yagci, and L. K. Toppare, “Synthesis, characterization, and electrochromic properties of conducting copolymers of 2-[(3-thienylcarbonyl)oxy]ethyl 3-thiophene carboxylate with thiophene and pyrrole,” JOURNAL OF MACROMOLECULAR SCIENCE-PURE AND APPLIED CHEMISTRY, pp. 937–947, 2004, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/47342.