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

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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.
Original languageEnglish
Pages (from-to)1834-1840
Number of pages7
JournalMacromolecular Rapid Communications
Volume30
Issue number21
DOIs
Publication statusPublished - 2 Nov 2009

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Keywords

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

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