A near-infrared fluorescent probe with an improved Stokes shift achieved by tuning the donor–acceptor–donor character of the rhodamine skeleton and its applications

Abstract

In this paper, we report a novel near-infrared (NIR) mitochondrion-targeted fluorescent probe, RQS, with an improved Stokes shift (96 nm) for the specific detection of mitochondrial mercury ion (Hg²⁺) because mitochondrion is one of the main targeted organelles of Hg²⁺. For the preparation of the probe, a novel asymmetrical fluorescent xanthene dye RQ was first synthesized by tuning the donor–acceptor–donor (D–A–D) character of the rhodamine skeleton, and then the probe RQS was constructed by the mechanism of mercury-promoted ring-opening reaction. As expected, RQS could be used for the specific detection of Hg²⁺ with high selectivity, high sensitivity, and a detection limit down to the nanomolar range (2 nM). Importantly, RQS is capable of specifically distributing in mitochondria, and thus detect Hg²⁺ in real-time and provided a potential tool for studying the cytotoxic mechanisms of Hg²⁺.