Synthesis, fluorescence property and cell imaging of a perylene diimide-based NIR fluorescent probe for hypochlorite with dual-emission fluorescence responses

Abstract

In this study, for the first time, a novel near-infrared and ratiometric fluorescent probe was conveniently synthesized by reacting PDI-based salicylaldehyde with 2-(hydrazonomethyl)phenol. The probe was designed based on the intramolecular charge transfer (ICT) mechanism and the intramolecular electron transfer (IET) mechanism, which can be blocked by the hypochlorite and a larger conjugation is formed within the probe. Due to the turn-on fluorescence responses triggered by the PET and ICT processes after the ClO⁻ addition, the probe produces simultaneous emission peaks at 600 nm and 820 nm. In addition, the probe shows a rapid fluorescence response towards the ClO⁻ ions within 5 s, a low detection limit (0.8 × 10⁻⁷ M), intense color changes (from purple to light green), excellent selectivity, and reversibility. Importantly, cell imaging experiments show that the probe can identify endogenous ClO⁻ successfully.