4.7 Article

Synthesis of 2-Azulenyltetrathiafulvalenes by Palladium-Catalyzed Direct Arylation of 2-Chloroazulenes with Tetrathiafulvalene and Their Optical and Electrochemical Properties

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 3, Pages 1657-1665

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b02818

Keywords

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Funding

  1. JSPS KAKENHI [25810019, 16K05679, 26410052]
  2. Faculty of Science, Shinshu University
  3. Grants-in-Aid for Scientific Research [16K05679, 17K05780, 26410052] Funding Source: KAKEN

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Tetrathiafulvalene (TTF) derivatives with 2-azulenyl substituents 5-11 were prepared by the palladium catalyzed direct arylation reaction of 2-chloroazulenes with TTF in good yield. Photophysical properties of these compounds were investigated by UV-vis spectroscopy and theoretical calculations. Redox behavior of the novel azulenesubstituted TTFs was examined by using cyclic voltammetry and differential pulse voltammetry, which revealed their multistep electrochemical oxidation and/or reduction properties. Moreover, these TTF derivatives showed significant spectral change in the visible region under the redox conditions.

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