A novel fluorescent probe based on a triphenylamine derivative for the detection of HSO3− with high sensitivity and selectivity

Abstract

A novel highly active fluorescence chemical sensor (TBQN) for HSO₃⁻ was synthesized by the Knoevenagel reaction based on triphenylamine–benzothiazole as a new fluorophore. The probe possessed good selectivity toward HSO₃⁻ and anti-interference ability with common ions. The fluorescence and UV-vis spectra of the TBQN probe were significantly changed after the addition of HSO₃⁻. At the same time, the probe solution released obvious green fluorescence. Moreover, the limit of detection for HSO₃⁻ was calculated to be 3.19 × 10^–8 M. The TBQN probe displayed a rapid response to HSO₃⁻ and it took about 3 min to complete the recognition. The detection mechanism is the nucleophilic addition reaction between HSO₃⁻ and –CC– in the probe molecule. The π-conjugation and ICT (intramolecular charge transfer) transition in the TBQN molecule were destroyed by this addition, which resulted in the change of the fluorescence before and after the addition of HSO₃⁻. Then, the mechanism was verified by theoretical calculations, ¹H NMR measurements and mass spectroscopy. In addition, the probe showed low cytotoxicity and could be used for biological imaging in RAW264.7 cells.