Synthesis and Electropolymerization of Bis(phenylthieno[3,2-b]thiophenes)- (4,4 '-dinonyl-2,2 '-bithiazole) co-monomer


Sezer E., OSKEN I., Çınar M., DEMIREL O., Ustamehmetoğlu B., Öztürk T.

ELECTROCHIMICA ACTA, vol.222, pp.1592-1603, 2016 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 222
  • Publication Date: 2016
  • Doi Number: 10.1016/j.electacta.2016.11.145
  • Journal Name: ELECTROCHIMICA ACTA
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1592-1603
  • Keywords: 4,4 '-Dinonyl-2,2 '-bithiazole and 3-phenylthieno[3,2-b]thiophene, Stille cross coupling, Electropolymerization, DFT, TRIFLUORIDE DIETHYL ETHERATE, ELECTROCHEMICAL IMPEDANCE SPECTROSCOPY, ORGANIC CONDUCTING POLYMERS, FLUORIDE-ETHYL ETHER, ANISOTROPIC DIELECTRICS, POLYTHIOPHENE FILMS, CONJUGATED POLYMER, IONIC-SOLUTIONS, THIN-FILMS, DERIVATIVES
  • Istanbul Technical University Affiliated: Yes

Abstract

Synthesis of comonomer possessing 4,4'-dinonyl-2,2'-bithiazole and 3-phenylthieno[3,2-b] thiophene units (PhTT-NBT-PhTT) was performed under Stille cross coupling condition. Its electropolymerization was conducted in the presence of trifluroborate-diethyl ether (BF3 center dot DEE) to lower the electrochemical polymerization potential through a complex formation between heteroaromatic monomers and boron trifluoride. Electrochemical properties of obtained P[PhTT] and P[PhTT-NBT-PhTT] films, such as effect of electrolyte, polymerization charge, potential limits on the redox behaviour were investigated. They were further characterized by UV-visible spectrophotometric measurements. Corresponding electrical equivalent circuit was applied to the experimental electrochemical impedance spectroscopy (EIS) data to explain the parameters of each element and the interface between the Pt/P[PhTT]/BF3 center dot DEE and Pt/P[PhTT-NBT-PhTT]/BF3 center dot DEE systems. The band gap of P[PhTT-NBT-PhTT was obtained as 2.04 eV by insitu spectroelectrochemical measurements. Frontier molecular orbitals and electropolymerization of the comonomer were assessed computationally. (C) 2016 Elsevier Ltd. All rights reserved.