Synthesis, characterization and electrochromic properties of copolymer of 3-{[4-(thien-3-yl-methoxy)phenoxy]methyl} thiophene with thiophene

Date

2006-08-01

Author

Erden, Ayca
Sahin, Elif
Gullu, Mustafa
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

183
views

0
downloads

(3- {[4-(Thien-3-yl-methoxy)phenoxy]methyl} thiophene) (TMPMT) was synthesized via the reaction of 3-bromomethyl-thiophene with hydroquinone and characterized by nuclear magnetic resonance (NMR) and Fourier transform infrared spectroscopy (FTIR). Electrochemical copolymerization of TMPMT with thiophene in acetonitrile/boron trifluoride diethyl etherate (AN/BFEE) solvent mixture was achieved using tetrabutylammonium tetrafluoroborate (TBAFB) as the supporting electrolyte. Resulting copolymer was characterized via cyclic voltammetry (CV), Fourier transform infrared spectroscopy (FTIR), scanning electron microscopy (SEM), four probe technique conductivity measurement and UV-Vis spectroscopy. Spectroelectrochemical analysis of the copolymer [P(TTMT-co-Th)] revealed that pi-pi* electronic transition occurs at 427 nm with a band gap value of 2.20 eV. Copolymer gives brown color at the fully reduced state whereas; at fully oxidized state the film has a gray-blue color. Kinetic studies were carried out at the maximum contrast wavelength upon measuring the percent transmittance, T% (7.6%) and switching time (2.0 s) to examine the switching ability of the copolymer. Dual type electrochromic device (ECD) of P(TMPMT-co-Th) and poly(3,4-ethylenedioxythiophene) (PEDOT) was constructed. Spectroelectrochemistry, switching ability, open circuit memory and stability of the device were examined by UV-Vis spectroscopy and cyclic voltammetry. The device switches between brown and blue at switching voltages of 0.0 V and 2.8 V with a short switching time of 1.4 s.

Subject Keywords

Organic Chemistry, General Physics and Astronomy, Polymers and Plastics

URI

https://hdl.handle.net/11511/37209

Journal

EUROPEAN POLYMER JOURNAL

DOI

https://doi.org/10.1016/j.eurpolymj.2006.03.011

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

Synthesis, characterization and electrochromic properties of a near infrared active conducting polymer of 1,4-di(selenophen-2-yl)-benzene Aydemir, Kadir; Tarkuc, Simge; Durmus, Asuman; Günbaş, Emrullah Görkem; Toppare, Levent Kamil (Elsevier BV, 2008-04-15) A novel selenophene-based monomer, 1,4-di(selenophen-2-yl)-benzene (DSB), was synthesized via Stille coupling reaction of 1,4-dibromobenzene and tributyl(2-selenophenyl)stannane. Conducting polymer (PDSB) was prepared electrochemically in the presence of tetrabutylammonium hexafluorophosphate (TBAPF(6)) as the supporting electrolyte in dichloromethane (DCM). The resulting conducting polymer was characterized by Cyclic Voltammetry, Fourier Transform Infrared and Ultraviolet-visible spectroscopy. Spectroelect...
Synthesis, characterization and electrochromic properties of conducting copolymers of 2,3-bis-[(3-thienylcarbonyl)oxy]propyl 3-thiophene carboxylate with thiophene and pyrrole Bulut, U; Toppare, Levent Kamil; Yilmaz, F; Yagci, Y (Elsevier BV, 2004-11-01) 2,3-bis-[(3-thienylcarbonyl)oxy]propyl 3-thiophene carboxylate (TOPT) was synthesized via the reaction of 3-thionylcarboxylic acid with glycerol, and electrochemically polymerized either with thiophene and pyrrole by using tetrabutylammonium tetrafluoroborate (TBAFB) as the supporting electrolyte in acetonitrile (AN). Characterization of the resulting copolymers was performed via cyclic voltammetry, FTIR, thermal gravimetry analysis (TGA), and scanning electron microscopy (SEM). Electrical conductivities we...
Synthesis and electrochemical characterization of fluorene and benzimidazole containing novel conjugated polymers: Effect of alkyl chain length on electrochemical properties Namal, Imge; Ozelcaglayan, Ali Can; Udum, Yasemin Arslan; Toppare, Levent Kamil (Elsevier BV, 2013-10-01) The synthesis and characterization of two donor acceptor type conjugated polymers were investigated. Electrochemical properties were examined by cyclic voltammetry, spectroelectrochemistry and kinetic studies. The increase in the alkyl chain length attached to the fluorene unit was investigated in terms of electrochemical properties. The synthesis was carried out via Stille coupling of 4,7-dibromo-4'-(tert-butyl)spiro[benzo[d]imidazole-2,1' cyclohexane] and 2,5-bis(tributylstannyl)thiophene with 9,9-dihexyl...
SYNTHESIS OF BLOCK COPOLYMERS VIA ANION-TO-RADICAL TRANSFORMATION HAZER, B; CAKMAK, I; KUCUKYAVUZ, S; NUGAY, T (Elsevier BV, 1992-10-01) Synthesis of (methyl methacrylate)-styrene block copolymers was carried out using anion-to-radical transformation. For this purpose, living polystyryl anion, prepared by using a new anionic difunctional initiator, 1,5-di(2-(3,3-dimethyl butyl-1-lithio)naphthalene, was terminated by the addition of 4,4'-bromomethyl dibenzoyl peroxide. Polystyrene samples having peroxide terminal groups were then used as initiators in the polymerization of methyl methacrylate. Block copolymers were characterized by spectrosco...
Synthesis and characterization of thiophene functionalized polystyrene copolymers and their electrochemical properties Sahin, E; Camurlu, P; Toppare, Levent Kamil; Mercore, VM; Cianga, I; Yagci, Y (Wiley, 2005-12-01) Thiophene functionalized polystyrene samples (TFPS) were synthesized by atom transfer radical polymerization (ATRP) of styrene, followed by Suzuki coupling with 3-thiophene (Th) boronic acid. Conducting graft polymer of TFPS with thiophene was achieved at 1.5 V in tetrabutylammonium tetrafluoroborate/dichloromethane (TBAFB/DM) by electrochemical methods. Spectroelectrochemical analysis of the resulting copolymers [P(TFPS-co-Th)] reflected electronic transitions at 449, 721 and 880 nm, revealing pi - pi* tra...

Citation Formats

A. Erden, E. Sahin, M. Gullu, and L. K. Toppare, “Synthesis, characterization and electrochromic properties of copolymer of 3-{[4-(thien-3-yl-methoxy)phenoxy]methyl} thiophene with thiophene,” EUROPEAN POLYMER JOURNAL, pp. 1866–1874, 2006, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/37209.