Synthesis, Photophysical and Electrochemical Properties of 1-, 2-, and 6-(2-Benzofuryl)azulenes

  • Taku Shoji
    Graduate School of Science and Technology, Shinshu University, Matsumoto, Nagano 390-8621, Japam
  • Yukino Ariga
    Graduate School of Science and Technology, Shinshu University, Matsumoto, Nagano 390-8621, Japam
  • Akari Yamazaki
    Graduate School of Science and Technology, Shinshu University, Matsumoto, Nagano 390-8621, Japam
  • Mayumi Uda
    Graduate School of Science and Technology, Shinshu University, Matsumoto, Nagano 390-8621, Japam
  • Takuya Nagasawa
    Graduate School of Science and Technology, Hirosaki University, Hirosaki, Aomori 036-8561, Japam
  • Shunji Ito
    Graduate School of Science and Technology, Hirosaki University, Hirosaki, Aomori 036-8561, Japam

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<jats:title>Abstract</jats:title> <jats:p>The synthesis of 2- and 6-(2-benzofuryl)azulenes was accomplished by the Sonogashira-Hagihara coupling reaction of the corresponding haloazulenes with 2-ethynylphenol. 1-(2-Benzofuryl)azulenes were prepared by the decarboxylation of the corresponding 3-methoxycarbonyl derivatives with 100% H3PO4, of which the synthesis has been reported by us, recently. The photophysical properties of the (2-benzofuryl)azulenes were investigated by UV/Vis and fluorescence spectroscopies that revealed their pronounced halochromic behavior and luminescent characteristics under the light-irradiation in acidic media. The electrochemical properties of (2-benzofuryl)azulenes were also evaluated by voltammetry experiments and spectroelectrochemistry measurements.</jats:p>

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