Synthesis, properties, and redox behavior of tris(1-azulenyltetracyanobutadiene) and tris[1-azulenylbis(tetracyanobutadiene)] chromophores connected to a 1,3,5-tri(1-azulenyl)benzene core

Taku Shoji, Akifumi Maruyama, Erika Shimomura, Daichi Nagai, Shunji Ito, Tetsuo Okujima, Kozo Toyota

研究成果: Article査読

16 被引用数 (Scopus)

抄録

Tris(1-azulenylacetylene) and tris(1-azulenylethynylarylacetylene) chromophores connected to a 1,3,5-tri(1-azulenyl)benzene core have been prepared by the Pd-catalyzed alkynylations of 1-ethynylazulene with tris(3-iodo-1-azulenyl)benzene or iodoarene derivatives substituted with a 1-azulenylethynyl group with tris(3-ethynyl-1-azulenyl)benzene under Sonogashira-Hagihara cross-coupling conditions. These compounds reacted with tetracyanoethylene in formal [2+2] cycloaddition-retroelectrocyclization reactions to afford the corresponding tris(1-azulenyltetracyanobutadiene) and tris[1-azulenylbis(tetracyanobutadiene)] chromophores in excellent yields. The redox behavior of the tetracyanobutadiene (TCBD) derivatives was examined by cyclic voltammetry (CV) and differential pulse voltammetry (DPV), which revealed their multistep electrochemical reduction properties. Moreover, significant color changes were observed by visible spectroscopy under the electrochemical reduction conditions. Tris(1-azulenyltetracyanobutadiene) and tris[1-azulenylbis(tetracyanobutadiene)] chromophores with a C3-symmetrical structure are prepared by the formal [2+2] cycloaddition-retroelectrocyclization reactions of tetracyanoethylene (TCNE) with the corresponding alkynes, and their redox behavior is examined by CV, differential pulse voltammetry (DPV), and spectroelectrochemical measurements.

本文言語English
ページ(範囲)1979-1990
ページ数12
ジャーナルEuropean Journal of Organic Chemistry
2015
9
DOI
出版ステータスPublished - 2015 3

ASJC Scopus subject areas

  • 物理化学および理論化学
  • 有機化学

フィンガープリント

「Synthesis, properties, and redox behavior of tris(1-azulenyltetracyanobutadiene) and tris[1-azulenylbis(tetracyanobutadiene)] chromophores connected to a 1,3,5-tri(1-azulenyl)benzene core」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

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