Synthesis of C3/C13‐Substituted Semi‐Synthetic Bacteriochlorophyll‐<i>a</i> Derivatives and Their Properties as Functional Dyes

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  • Shin‐ichi Sasaki
    Faculty of Bioscience Nagahama Institute of Bio-Science and Technology Nagahama Shiga 526-0829 Japan
  • Yuki Hashimoto
    Graduate School of Life Sciences Ritsumeikan University Kusatsu Shiga 525-8577 Japan
  • Yusuke Kinoshita
    Graduate School of Life Sciences Ritsumeikan University Kusatsu Shiga 525-8577 Japan
  • Hitoshi Tamiaki
    Graduate School of Life Sciences Ritsumeikan University Kusatsu Shiga 525-8577 Japan
  • Shengnan Duan
    Key Laboratory of Physics and Technology for Advanced Batteries (Ministry of Education), College of Physics Jilin University Changchun 130012 PR China
  • Xiao‐Feng Wang
    Key Laboratory of Physics and Technology for Advanced Batteries (Ministry of Education), College of Physics Jilin University Changchun 130012 PR China
  • Yoshitaka Saga
    Faculty of Science and Engineering Kindai University Higashi-Osaka Osaka 577-8502 Japan
  • Hiroaki Yamamoto
    Faculty of Bioscience Nagahama Institute of Bio-Science and Technology Nagahama Shiga 526-0829 Japan
  • Toshitaka Ikeuchi
    Faculty of Bioscience Nagahama Institute of Bio-Science and Technology Nagahama Shiga 526-0829 Japan
  • Nobue Shishioh
    Faculty of Bioscience Nagahama Institute of Bio-Science and Technology Nagahama Shiga 526-0829 Japan

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<jats:title>Abstract</jats:title><jats:p>Natural bacteriochlorophyll‐<jats:italic>a</jats:italic> was converted to chemically stable free‐base derivatives with different substituents along the y‐axis. Compared to the natural type compound methyl pyrobacteriopheophorbide‐<jats:italic>a</jats:italic> possessing the C3‐acetyl and C13‐keto‐carbonyl groups, its deoxo‐bacteriochlorin lacking the C3‐ and C13‐carbonyl groups showed a blue‐shift of the Q<jats:sub>y</jats:sub> peak. On the other hand, introduction of the dicyanomethylene group(s) at the 3<jats:sup>1</jats:sup>‐ and/or 13<jats:sup>1</jats:sup>‐position(s) caused an opposite effect due to its electron‐withdrawing ability as well as the expansion of the π‐conjugation system along the y‐axis, and the Q<jats:sub>y</jats:sub> peak maxima were red‐shifted to around 780 nm. These semi‐synthetic bacteriochlorins in an aerated solvent could generate singlet oxygen upon illumination with far‐red light, which was evaluated by mouse B16 melanoma cells to be applicable as photosensitizers. Besides this, it was demonstrated that they could be utilized as electron‐donating materials combined with fullerene derivatives to fabricate bulk‐heterojunction organic solar cells.</jats:p>

Journal

  • ChemPhotoChem

    ChemPhotoChem 4 (12), 5399-5407, 2020-07-30

    Wiley

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