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Turn-On Mode Fluorescence Switch by Using Negative Photochromic Imidazole Dimer

  • Katsuya Mutoh
    Katsuya Mutoh
    Department of Chemistry, School of Science and Engineering, Aoyama Gakuin University, 5-10-1 Fuchinobe, Chuo-ku, Sagamihara, Kanagawa 252-5258, Japan
  • Nanae Miyashita
    Nanae Miyashita
    Department of Chemistry, School of Science and Engineering, Aoyama Gakuin University, 5-10-1 Fuchinobe, Chuo-ku, Sagamihara, Kanagawa 252-5258, Japan
  • Kaho Arai
    Kaho Arai
    Department of Chemistry, School of Science and Engineering, Aoyama Gakuin University, 5-10-1 Fuchinobe, Chuo-ku, Sagamihara, Kanagawa 252-5258, Japan
    More by Kaho Arai
  • , and 
  • Jiro Abe*
    Jiro Abe
    Department of Chemistry, School of Science and Engineering, Aoyama Gakuin University, 5-10-1 Fuchinobe, Chuo-ku, Sagamihara, Kanagawa 252-5258, Japan
    *[email protected]
    More by Jiro Abe
Cite this: J. Am. Chem. Soc. 2019, 141, 14, 5650–5654
Publication Date (Web):March 19, 2019
Copyright © 2019 American Chemical Society

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    Abstract Image

    The development of fluorescence switchable molecules in several polar and apolar environments has been required for fluorescence imaging of nanostructures. Photochromic molecules are an important class for the reversible light-triggered fluorescence switching. Although many studies of fluorescence switching by using photochromic reactions have been reported, the report of photochromic molecules reversibly showing turn-on mode fluorescence switching has been limited in spite of their importance. Herein, we report the photoactivatable fluorescence based on negative photochromism, where the absorption spectrum of the compound after irradiation is blue-shifted relative to that before irradiation. We introduced naphthalimide units as a green fluorophore to the negative photochromic binaphthyl-bridged imidazole dimer. The fluorescence of the naphthalimide unit is efficiently quenched in the initial colored isomer (fluorescence quantum yield: Φfluo. = 0.01) by Förster resonance energy transfer. In contrast, the fluorescence quantum yield increases up to 0.75 in the transient isomer formed by the negative photochromic reaction. The fluorescence intensity thermally decreases with the thermal back reaction to form the original stable colored form. These results indicate that the negative photochromic molecules are suitable for turn-on mode fluorescence switches and will give an attractive insight for the development of reversible fluorescence switching molecules.

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