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Two sensors,  1  with a spirolactone group and  2  with a spirolactam group containing a phenyl isothiocyanate moiety, based on rhodol, were designed and synthesized in order to obtain materials with excellent optical properties for the detection of environmentally and biologically important Hg 2+  and hypochlorous acid (HClO) ions. The crystal structure of  1  revealed two moieties, a rhodamine‐like portion with a spirolactone and a fluorescein‐like portion without a spirolactone. In the absence of analyte,  1  produced an optical output with a maximum absorption and emission at 475 and 570 nm, respectively, which was attributed to the fluorescein‐like moiety without a spirolactone. In contrast, the rhodamine‐like moiety containing a spirolactone was activated by the addition of H +  or Hg 2+  ions, and  1  yielded new absorption and emission peaks at 530 and 612 nm, respectively. Further functionalization with a phenyl isothiocyanate group afforded  2 , a fluorescent probe for HClO. High selectivity and sensitivity towards the hypochlorite ion were anticipated, owing to the stoichiometric and irreversible formation of a thiosemicarbazide group, which led to dramatic fluorescence responses. With good functionality at physiological pH, probe  2  was successfully used to image HClO in HeLa cells.

Rhodol Derivatives as Selective Fluorescent Probes for the Detection of Hg II Ions and the Bioimaging of Hypochlorous Acid