Journal
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
Volume 85, Issue 7, Pages 761-773Publisher
CHEMICAL SOC JAPAN
DOI: 10.1246/bcsj.20120037
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Funding
- Ministry of Education, Culture, Sports, Science and Technology, Japan [22850007]
- Grants-in-Aid for Scientific Research [22850007] Funding Source: KAKEN
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Mono-, bis-, tris-, and tetrakis[(1-azulenylethynyl)phenylethynyl- and (1-azulenylethynyl)-2-thienylethynyl]benzenes have been prepared by Pd-catalyzed alkynylation of iodobenzene derivatives or 2-iodothiophene derivatives substituted by 1-azulenylethynyl group with polyethynylbenzenes under Sonogashira-Hagihara cross-coupling conditions. These compounds reacted with tetracyanoethylene (TCNE) in a formal [2 + 2] cycloaddition-cycloreversion reaction to afford the corresponding 1,1,4,4-tetracyano-2-(5-isopropyl-3-methoxycarbonyl-l-azulenyl)-1,3-butadien-3-yl chromophores in excellent yields. The redox behavior of the novel azulene-substituted tetracyanobutadiene (TCBD) derivatives was examined by cyclic voltammetry (CV) and differential pulse voltammetry (DPV), which revealed their multistep electrochemical reduction properties. Moreover, a significant color change was observed by visible spectroscopy under the electrochemical reduction conditions.
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