Halochromism of 2-indolinone fluorophore based on the deprotonation of an acidic C–H bond

Abstract

We have disclosed a new halochromic fluorescent dye based on the deprotonation from an acidic C–H bond. The dye consisting of a 2-indolinone skeleton and a benzothiazole ring exhibited an obvious red shift in its photoluminescence spectra in response to the presence of bases. Structural analyses with 1H NMR measurements and theoretical calculations suggested that the π-conjugated system of the dye was expanded by the deprotonation of the acidic C–H bond on the 2-indolinone skeleton. This structural change would contribute to the red shift of photoluminescence and accelerate the radiative decay from the excited state.