Reactions between 1-ethynylazulenes and 7,7,8,8-tetracyanoquinodimethane (TCNQ): Preparation, properties, and redox behavior of novel azulene-substituted redox-active chromophores

Taku Shoji, Shunji Ito, Kozo Toyota, Takeaki Iwamoto, Masafumi Yasunami, Noboru Morita

Research output: Contribution to journalArticlepeer-review

48 Citations (Scopus)

Abstract

[2+2] Cycloaddition/cycloreversion reactions between TCNQ and mono- or bis[2-(azulen-1-yl)ethynyl]benzene or -thiophene derivatives were examined: the corresponding TCNQ adducts, novel azulene-substituted redox-active chromophores, were produced in excellent yields. TCNE/TCNQ double adducts were also prepared both by stepwise and by one-pot cascade reactions. The redox behavior of these novel azulene-substituted chromophores was examined by cyclic voltammetry (CV) and differential pulse voltammetry (DPV). Significant color changes in these azulene-substituted chromophores under electrochemical reduction conditions were observed by visible spectroscopy.

Original languageEnglish
Pages (from-to)4316-4324
Number of pages9
JournalEuropean Journal of Organic Chemistry
Issue number25
DOIs
Publication statusPublished - 2009 Sep 1

Keywords

  • Azulenes
  • Cycloaddition
  • Donor-acceptor systems
  • Electrochromism
  • Redox chemistry

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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