Helicene–Fluorescein Hybrids: A Reversible Base‐Triggered (Chir)optical Switch with Sign Inversion of Circularly Polarized Luminescence

DOI Web Site 参考文献73件 オープンアクセス
  • Sorachi Miwa
    Graduate School of Pharmaceutical Sciences Kyoto University Yoshida, Sakyo-ku Kyoto 606-8501 Japan
  • Daichi Mizutani
    Graduate School of Pharmaceutical Sciences Kyoto University Yoshida, Sakyo-ku Kyoto 606-8501 Japan
  • Kenichi Kawano
    Graduate School of Pharmaceutical Sciences Kyoto University Yoshida, Sakyo-ku Kyoto 606-8501 Japan
  • Katsumi Matsuzaki
    Graduate School of Pharmaceutical Sciences Kyoto University Yoshida, Sakyo-ku Kyoto 606-8501 Japan
  • Yuuya Nagata
    Institute for Chemical Reaction Design and Discovery (WPIICReDD) Hokkaido University Hokkaido Kita 21, Nishi 10 Kita-ku, Sapporo Hokkaido 001-0021 Japan
  • Kazunori Tsubaki
    Graduate School of Life and Environmental Sciences Kyoto Prefectural University Shimogamo Hangi-cho Sakyo-ku Kyoto 606-8522 Japan
  • Kiyosei Takasu
    Graduate School of Pharmaceutical Sciences Kyoto University Yoshida, Sakyo-ku Kyoto 606-8501 Japan
  • Hiroshi Takikawa
    Graduate School of Pharmaceutical Sciences Kyoto University Yoshida, Sakyo-ku Kyoto 606-8501 Japan

書誌事項

公開日
2025-02-12
資源種別
journal article
権利情報
  • http://creativecommons.org/licenses/by-nc-nd/4.0/
  • http://creativecommons.org/licenses/by-nc-nd/4.0/
DOI
  • 10.1002/chem.202500335
公開者
Wiley

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説明

<jats:title>Abstract</jats:title><jats:p>Novel circularly‐polarized‐luminescence (CPL) materials were designed and synthesized by integrating the intrinsic chirality of helicene with the acid/base‐responsive properties of fluorescein. The synthesized helicene–fluorescein hybrids exhibit reversible switching between blue fluorescence under neutral conditions and red fluorescence under basic conditions. Furthermore, these hybrid compounds demonstrate unique chiroptical switching behavior with a rare base‐triggered CPL sign inversion, where (<jats:italic>P</jats:italic>)‐isomers show a negative CPL signal around 450 nm under neutral conditions and a positive signal around 620 nm under basic conditions, with three‐fold enhanced dissymmetry factors (|<jats:italic>g</jats:italic><jats:sub>lum</jats:sub>|) under basic conditions. The structural basis for this switching was elucidated through TD‐DFT calculations, revealing distinct angles between magnetic and electric transition dipole moments in closed versus open forms. Live‐cell imaging experiments using HeLa cells revealed that the hybrid compounds exhibit intracellular red emission with minimal cytotoxicity, thus promising potential as chiral fluorescent probes for biological applications.</jats:p>

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