A red-emissive benzothiazole-based luminophore with ESIPT and AIE natures and its application for detecting and imaging hypochlorous acid

A new "ESIPT + AIE" based dye of benzothiazole with red emission and a large Stokes shift was constructed by combining 2-(2′-hydroxyphenyl)benzothiazole as the ESIPT unit and α-cyanostilbene as the AIE unit. The compound BACN was found to be a ideal HClO chemosensor, and presented palpable fluorescence and colorimetric responses toward HClO via the HClO-trigged oxidation cleavage of the ethylene bridge activated by the electron withdrawing cyano group. BACN was capable of recognizing HClO rapidly (12 s) and sensitively under physiological conditions, with good selectivity over other biologically pertinent substances. Thanks to strong red emission (λem = 606 nm) and large Stokes shift (213 nm) resulted from the combination of ESIPT and AIE effects, it was successfully utilized for the recognition of exogenous and endogenous HClO in living HeLa cells.