Electrochemical polymerisation of n-arylated and n-alkylated EDOT-substituted pyrrolo[3,4-c]pyrrole-1,4-dione (dpp) derivatives: influence of substitution pattern on optical and electronic properties

Kai Zhang, Bernd Tieke, John C. Forgie, Peter Skabara

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

New pyrrolo[3,4-c]pyrrole-1,4-dione (DPP) derivatives carrying 3,4-ethylenedioxy-thiophenylphenyl (EDOT-phenyl) substituent groups in the 3- and 6-position, or in the 2- and 5-position of the DPP chromophore were synthesised and electrochemically polymerised. The properties of the polymers were investigated using cyclic voltammetry and UV/Vis absorption spectroscopy. It was found that the optical and electronic properties differ greatly between the two polymers. Materials with EDOT-phenyl groups in the 3- and 6-positions represent conjugated polymers with a low oxidation potential and reversible electrochromic properties, whereas the polymer with EDOT-phenyl groups in the 2- and 5-positions is non-conjugated and possesses a high oxidation potential and irreversible redox behaviour.
LanguageEnglish
Pages1834-1840
Number of pages7
JournalMacromolecular Rapid Communications
Volume30
Issue number21
DOIs
Publication statusPublished - 2 Nov 2009

Fingerprint

Pyrroles
Electropolymerization
Electronic properties
Polymers
Substitution reactions
Optical properties
Derivatives
Oxidation
Conjugated polymers
Chromophores
Ultraviolet spectroscopy
Absorption spectroscopy
Cyclic voltammetry

Keywords

  • DPP
  • electrochromism
  • electropolymerisation
  • monomers
  • N-aryl-DPP
  • organic electronics
  • properties
  • pyrrolo[3
  • 4-c]pyrrole-1
  • 4-dione
  • 3
  • 4-ethylenedioxy-thiophene

Cite this

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title = "Electrochemical polymerisation of n-arylated and n-alkylated EDOT-substituted pyrrolo[3,4-c]pyrrole-1,4-dione (dpp) derivatives: influence of substitution pattern on optical and electronic properties",
abstract = "New pyrrolo[3,4-c]pyrrole-1,4-dione (DPP) derivatives carrying 3,4-ethylenedioxy-thiophenylphenyl (EDOT-phenyl) substituent groups in the 3- and 6-position, or in the 2- and 5-position of the DPP chromophore were synthesised and electrochemically polymerised. The properties of the polymers were investigated using cyclic voltammetry and UV/Vis absorption spectroscopy. It was found that the optical and electronic properties differ greatly between the two polymers. Materials with EDOT-phenyl groups in the 3- and 6-positions represent conjugated polymers with a low oxidation potential and reversible electrochromic properties, whereas the polymer with EDOT-phenyl groups in the 2- and 5-positions is non-conjugated and possesses a high oxidation potential and irreversible redox behaviour.",
keywords = "DPP, electrochromism, electropolymerisation, monomers, N-aryl-DPP, organic electronics, properties, pyrrolo[3, 4-c]pyrrole-1, 4-dione, 3, 4-ethylenedioxy-thiophene",
author = "Kai Zhang and Bernd Tieke and Forgie, {John C.} and Peter Skabara",
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Electrochemical polymerisation of n-arylated and n-alkylated EDOT-substituted pyrrolo[3,4-c]pyrrole-1,4-dione (dpp) derivatives: influence of substitution pattern on optical and electronic properties. / Zhang, Kai; Tieke, Bernd; Forgie, John C.; Skabara, Peter.

In: Macromolecular Rapid Communications, Vol. 30, No. 21, 02.11.2009, p. 1834-1840.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Electrochemical polymerisation of n-arylated and n-alkylated EDOT-substituted pyrrolo[3,4-c]pyrrole-1,4-dione (dpp) derivatives: influence of substitution pattern on optical and electronic properties

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AU - Tieke, Bernd

AU - Forgie, John C.

AU - Skabara, Peter

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AB - New pyrrolo[3,4-c]pyrrole-1,4-dione (DPP) derivatives carrying 3,4-ethylenedioxy-thiophenylphenyl (EDOT-phenyl) substituent groups in the 3- and 6-position, or in the 2- and 5-position of the DPP chromophore were synthesised and electrochemically polymerised. The properties of the polymers were investigated using cyclic voltammetry and UV/Vis absorption spectroscopy. It was found that the optical and electronic properties differ greatly between the two polymers. Materials with EDOT-phenyl groups in the 3- and 6-positions represent conjugated polymers with a low oxidation potential and reversible electrochromic properties, whereas the polymer with EDOT-phenyl groups in the 2- and 5-positions is non-conjugated and possesses a high oxidation potential and irreversible redox behaviour.

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KW - electropolymerisation

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KW - N-aryl-DPP

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