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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>"}]}],"creator":[{"@id":"https://cir.nii.ac.jp/crid/1380588381069802242","@type":"Researcher","foaf:name":[{"@value":"Sorachi Miwa"}],"jpcoar:affiliationName":[{"@value":"Graduate School of Pharmaceutical Sciences Kyoto University  Yoshida, Sakyo-ku Kyoto 606-8501 Japan"}]},{"@id":"https://cir.nii.ac.jp/crid/1380588381069802112","@type":"Researcher","foaf:name":[{"@value":"Daichi Mizutani"}],"jpcoar:affiliationName":[{"@value":"Graduate School of Pharmaceutical Sciences Kyoto University  Yoshida, Sakyo-ku Kyoto 606-8501 Japan"}]},{"@id":"https://cir.nii.ac.jp/crid/1380588381069802113","@type":"Researcher","foaf:name":[{"@value":"Kenichi Kawano"}],"jpcoar:affiliationName":[{"@value":"Graduate School of Pharmaceutical Sciences Kyoto University  Yoshida, 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