Glycolated Thiophene-Tetrafluorophenylene Copolymers for Bioelectronic Applications: Synthesis by Direct Heteroarylation Polymerisation

Zachary S. Parr; Roman Halaksa; Peter A. Finn; Reem B. Rashid; Alexander Kovalenko; Martin Weiter; Jonathan Rivnay; Jozef Krajčovič; Christian B. Nielsen

doi:10.1002/cplu.201900254

Glycolated Thiophene-Tetrafluorophenylene Copolymers for Bioelectronic Applications: Synthesis by Direct Heteroarylation Polymerisation

Zachary S. Parr, Roman Halaksa, Peter A. Finn, Reem B. Rashid, Alexander Kovalenko, Martin Weiter, Jonathan Rivnay, Jozef Krajčovič, Christian B. Nielsen^*

^*Corresponding author for this work

Biomedical Engineering

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

26 Scopus citations

Abstract

A series of copolymers containing a glycolated 1,4-dithienyl-2,3,5,6-tetrafluorophenylene unit copolymerized with thiophene, bithiophene, thienothiophene and 1,2,4,5-tetrafluorobenzene comonomer units were designed and synthesised by direct heteroarylation polymerisation. The optical, electrochemical, electrochromic and solid-state structural properties of the copolymers were investigated. The copolymers exhibit stable redox properties in organic solvents and promising redox properties in thin film configuration with an aqueous electrolyte. Finally, the potential of the copolymers as active materials in organic electrochemical transistors (OECTs) was assessed, and promising performance was shown as an accumulation-mode OECT material with a peak transconductance of 0.17 mS and a good on/off ratio of 10⁵ for the thiophene copolymer.

Original language	English (US)
Pages (from-to)	1384-1390
Number of pages	7
Journal	ChemPlusChem
Volume	84
Issue number	9
DOIs	https://doi.org/10.1002/cplu.201900254
State	Published - Sep 1 2019

Funding

The authors acknowledge the Academy of Medical Sciences & Wellcome Trust (SBF002/1158), the Czech Science Foundation (project 17-24707 S) and the Materials Research Institute for financial support. The authors thank Dr. Michal Kalina for GPC measurements.

Keywords

direct heteroarylation
organic electrochemical transistors
polymerisation
semiconductors
thiophenes

ASJC Scopus subject areas

General Chemistry

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10.1002/cplu.201900254

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title = "Glycolated Thiophene-Tetrafluorophenylene Copolymers for Bioelectronic Applications: Synthesis by Direct Heteroarylation Polymerisation",

abstract = "A series of copolymers containing a glycolated 1,4-dithienyl-2,3,5,6-tetrafluorophenylene unit copolymerized with thiophene, bithiophene, thienothiophene and 1,2,4,5-tetrafluorobenzene comonomer units were designed and synthesised by direct heteroarylation polymerisation. The optical, electrochemical, electrochromic and solid-state structural properties of the copolymers were investigated. The copolymers exhibit stable redox properties in organic solvents and promising redox properties in thin film configuration with an aqueous electrolyte. Finally, the potential of the copolymers as active materials in organic electrochemical transistors (OECTs) was assessed, and promising performance was shown as an accumulation-mode OECT material with a peak transconductance of 0.17 mS and a good on/off ratio of 105 for the thiophene copolymer.",

keywords = "direct heteroarylation, organic electrochemical transistors, polymerisation, semiconductors, thiophenes",

author = "Parr, \{Zachary S.\} and Roman Halaksa and Finn, \{Peter A.\} and Rashid, \{Reem B.\} and Alexander Kovalenko and Martin Weiter and Jonathan Rivnay and Jozef Kraj{\v c}ovi{\v c} and Nielsen, \{Christian B.\}",

note = "Publisher Copyright: {\textcopyright} 2019 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2019",

month = sep,

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doi = "10.1002/cplu.201900254",

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T2 - Synthesis by Direct Heteroarylation Polymerisation

AU - Parr, Zachary S.

AU - Halaksa, Roman

AU - Finn, Peter A.

AU - Rashid, Reem B.

AU - Kovalenko, Alexander

AU - Weiter, Martin

AU - Rivnay, Jonathan

AU - Krajčovič, Jozef

AU - Nielsen, Christian B.

PY - 2019/9/1

Y1 - 2019/9/1

N2 - A series of copolymers containing a glycolated 1,4-dithienyl-2,3,5,6-tetrafluorophenylene unit copolymerized with thiophene, bithiophene, thienothiophene and 1,2,4,5-tetrafluorobenzene comonomer units were designed and synthesised by direct heteroarylation polymerisation. The optical, electrochemical, electrochromic and solid-state structural properties of the copolymers were investigated. The copolymers exhibit stable redox properties in organic solvents and promising redox properties in thin film configuration with an aqueous electrolyte. Finally, the potential of the copolymers as active materials in organic electrochemical transistors (OECTs) was assessed, and promising performance was shown as an accumulation-mode OECT material with a peak transconductance of 0.17 mS and a good on/off ratio of 105 for the thiophene copolymer.

AB - A series of copolymers containing a glycolated 1,4-dithienyl-2,3,5,6-tetrafluorophenylene unit copolymerized with thiophene, bithiophene, thienothiophene and 1,2,4,5-tetrafluorobenzene comonomer units were designed and synthesised by direct heteroarylation polymerisation. The optical, electrochemical, electrochromic and solid-state structural properties of the copolymers were investigated. The copolymers exhibit stable redox properties in organic solvents and promising redox properties in thin film configuration with an aqueous electrolyte. Finally, the potential of the copolymers as active materials in organic electrochemical transistors (OECTs) was assessed, and promising performance was shown as an accumulation-mode OECT material with a peak transconductance of 0.17 mS and a good on/off ratio of 105 for the thiophene copolymer.

KW - direct heteroarylation

KW - organic electrochemical transistors

KW - polymerisation

KW - semiconductors

KW - thiophenes

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Glycolated Thiophene-Tetrafluorophenylene Copolymers for Bioelectronic Applications: Synthesis by Direct Heteroarylation Polymerisation

Abstract

Funding

Keywords

ASJC Scopus subject areas

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