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

E. Sezer; I. Osken; M. E. Cinar; O. Demirel; B. Ustamehmetoğlu; T. Ozturk

doi:10.1016/j.electacta.2016.11.145

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

E. Sezer^*, I. Osken, M. E. Cinar, O. Demirel, B. Ustamehmetoğlu, T. Ozturk

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

16 Citations (Scopus)

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·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·DEE and Pt/P[PhTT-NBT-PhTT]/BF₃·DEE systems. The band gap of P[PhTT-NBT-PhTT was obtained as 2.04 eV by in-situ spectroelectrochemical measurements. Frontier molecular orbitals and electropolymerization of the comonomer were assessed computationally.

Original language	English
Pages (from-to)	1592-1603
Number of pages	12
Journal	Electrochimica Acta
Volume	222
DOIs	https://doi.org/10.1016/j.electacta.2016.11.145
Publication status	Published - 20 Dec 2016

Bibliographical note

Publisher Copyright:
© 2016 Elsevier Ltd

Keywords

4,4'-Dinonyl-2,2'-bithiazole and 3-phenylthieno[3,2-b]thiophene
DFT
Electropolymerization
Stille cross coupling

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10.1016/j.electacta.2016.11.145

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

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·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·DEE and Pt/P[PhTT-NBT-PhTT]/BF3·DEE systems. The band gap of P[PhTT-NBT-PhTT was obtained as 2.04 eV by in-situ spectroelectrochemical measurements. Frontier molecular orbitals and electropolymerization of the comonomer were assessed computationally.",

keywords = "4,4'-Dinonyl-2,2'-bithiazole and 3-phenylthieno[3,2-b]thiophene, DFT, Electropolymerization, Stille cross coupling",

author = "E. Sezer and I. Osken and Cinar, {M. E.} and O. Demirel and B. Ustamehmetoğlu and T. Ozturk",

note = "Publisher Copyright: {\textcopyright} 2016 Elsevier Ltd",

year = "2016",

month = dec,

day = "20",

doi = "10.1016/j.electacta.2016.11.145",

language = "English",

volume = "222",

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TY - JOUR

T1 - Synthesis and Electropolymerization of Bis(phenylthieno[3,2-b]thiophenes)– (4,4'-dinonyl-2,2'-bithiazole) co-monomer

AU - Sezer, E.

AU - Osken, I.

AU - Cinar, M. E.

AU - Demirel, O.

AU - Ustamehmetoğlu, B.

AU - Ozturk, T.

PY - 2016/12/20

Y1 - 2016/12/20

N2 - 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·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·DEE and Pt/P[PhTT-NBT-PhTT]/BF3·DEE systems. The band gap of P[PhTT-NBT-PhTT was obtained as 2.04 eV by in-situ spectroelectrochemical measurements. Frontier molecular orbitals and electropolymerization of the comonomer were assessed computationally.

AB - 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·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·DEE and Pt/P[PhTT-NBT-PhTT]/BF3·DEE systems. The band gap of P[PhTT-NBT-PhTT was obtained as 2.04 eV by in-situ spectroelectrochemical measurements. Frontier molecular orbitals and electropolymerization of the comonomer were assessed computationally.

KW - 4,4'-Dinonyl-2,2'-bithiazole and 3-phenylthieno[3,2-b]thiophene

KW - DFT

KW - Electropolymerization

KW - Stille cross coupling

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DO - 10.1016/j.electacta.2016.11.145

M3 - Article

AN - SCOPUS:85027933601

SN - 0013-4686

VL - 222

SP - 1592

EP - 1603

JO - Electrochimica Acta

JF - Electrochimica Acta

ER -

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

Abstract

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Keywords

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