Electrosynthesis of 2,7-linked polycarbazole derivatives to realize low-bandgap electroactive polymers

Kohsuke Kawabata, Hiromasa Goto

Research output: Contribution to journalArticle

31 Citations (Scopus)

Abstract

Poly(2,7-carbazole) derivatives have been synthesized because they have more extended conjugation lengths and lower energy bandgaps than poly(3,6-carbazole)s; however, few studies regarding electrochemical synthesis of poly(2,7-carbazole)s have been reported. Here, a series of N-alkylated-2,7-di(2-furyl)carbazoles, N-butyl-2,7-di(2-thienyl)carbazole, and N-butyl-2,7-di(2-(3,4-ethylenedioxthienyl))carbazole, were synthesized to obtain electroactive films of poly(2,7-carbazole) derivatives by electrochemical polymerization. Cyclic voltammetry revealed that these monomers have excellent polymerization activity, due to their low oxidation potentials (<0.57 V vs. ferrocene (Fc/Fc+)), and the corresponding polymers exhibit good redox properties. The energy bandgaps of the polymers obtained from optical absorption spectra range from 2.1 to 2.3 eV. Among the polymers, poly[N-butyl-2,7-di(2-(3,4-ethylenedioxthienyl))carbazole] shows the lowest bandgap energy of 2.1 eV, which is lower than that of previously reported poly(3,6-carbazole) analogues (2.4 eV). This polymer exhibits a significant color change from red in the oxidized state to blue in the reduced state during an electrochemical redox process. The electrochemical and optical properties of the monomers are dependent on external heteroaromatic rings attached to the 2 and 7 positions of the carbazole unit.

Original languageEnglish
Pages (from-to)2290-2298
Number of pages9
JournalSynthetic Metals
Volume160
Issue number21-22
DOIs
Publication statusPublished - 2010 Nov

Keywords

  • Electrochemical polymerization
  • Electrochromism
  • Poly(2,7-carbazole)
  • π-Conjugated polymer

ASJC Scopus subject areas

  • Electronic, Optical and Magnetic Materials
  • Condensed Matter Physics
  • Mechanics of Materials
  • Mechanical Engineering
  • Metals and Alloys
  • Materials Chemistry

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