A highly selective turn-on fluorescent and chromogenic probe for CN− and its applications in imaging of living cells and zebrafish in vivo

Abstract

Herein, we report a novel Schiff base “turn-on” fluorescent and chromogenic probe N′-(3-(benzo[d]thiazol-2-yl)-2-hydroxybenzylidene)-4-(dimethylamino)-benzohydrazide (BHDB) for CN− detection under physiological pH, based on nucleophilic reaction of imine (CHN) and CN−, exhibiting almost 66-fold fluorescence increase and a remarkable color change from colorless to yellow. The experimentally observed changes in the spectral properties of the probe upon addition of CN− were systematically studied using high resolution electrospray ionization mass spectrometry (HR-ESI-MS), proton nuclear magnetic resonance (1H-NMR), and time-dependent density functional theory (TDDFT) calculations. Using the fluorescence spectra changes, we found a detection limit for CN− of 0.15μmolL−1, far lower than the maximum permissive level of CN− (1.9μmolL−1) in drinking water recommended by World Health Organization (WHO). Moreover, the novel probe demonstrated fluorescence imaging of CN− in living cells and zebrafish, suggesting its potential in clinical diagnostics.