Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2009, Issue 25, Pages 4316-4324Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200900539
Keywords
Azulenes; Cycloaddition; Donor-acceptor systems; Electrochromism; Redox chemistry
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Funding
- International Center of Research & Education for Molecular Complex Chemistry of the Ministry of Education, Culture, Sports, Science, and Technology.. Japan
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[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. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
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