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Electrochemically Active Cross-Linking Reaction for Fluorescent Labeling of Aliphatic Alkenes

Authors

  • Dr. Shokaku Kim,

    1. Laboratory of Bio-organic Chemistry, Tokyo University of Agriculture and Technology, 3-5-8 Saiwai-cho, Fuchu, Tokyo 183-8509 (Japan), Fax: (+81) 42-367-5761
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  • Kumi Hirose,

    1. Toppan Forms Co. Ltd. 1-2-6 Owada-cho, Hachioji, Tokyo 192-0045 (Japan)
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  • Jumpei Uematsu,

    1. Laboratory of Bio-organic Chemistry, Tokyo University of Agriculture and Technology, 3-5-8 Saiwai-cho, Fuchu, Tokyo 183-8509 (Japan), Fax: (+81) 42-367-5761
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  • Yuzuru Mikami,

    1. Laboratory of Bio-organic Chemistry, Tokyo University of Agriculture and Technology, 3-5-8 Saiwai-cho, Fuchu, Tokyo 183-8509 (Japan), Fax: (+81) 42-367-5761
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  • Prof. Dr. Kazuhiro Chiba

    Corresponding author
    1. Laboratory of Bio-organic Chemistry, Tokyo University of Agriculture and Technology, 3-5-8 Saiwai-cho, Fuchu, Tokyo 183-8509 (Japan), Fax: (+81) 42-367-5761
    • Laboratory of Bio-organic Chemistry, Tokyo University of Agriculture and Technology, 3-5-8 Saiwai-cho, Fuchu, Tokyo 183-8509 (Japan), Fax: (+81) 42-367-5761
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Abstract

Although cross-linking reactions serve as a valuable tool for the integration of two or more functionalities or properties, the application of electrochemical synthesis to cross-linking reactions is restricted due to the difficulty of mass transfer. Thus, the primary purpose of this research is to explore electrochemical cross-linking systems to construct a fluorescent probe, triggered by the formation of a covalent linkage. The second purpose is to apply the probe to insoluble targets. Towards these goals, a combination of electrochemically active phenol derivatives and aliphatic alkenes were employed to form polycyclic compounds. Several of the dihydrobenzofuran derivatives formed through [3+2] cyclization reactions exhibited fluorescence. Furthermore, this approach allowed the effective modification of alkene-modified silica gel with electrochemically active species, which enables the construction of fluorescent probes that are triggered by C[BOND]C bond formation.

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