A NIR fluorescent probe for the detection and visualization of hydrogen sulfide using the aldehyde group assisted thiolysis of dinitrophenyl ether strategy.

In view of the significant physiological and pathological roles HS plays in living systems, it is crucial to develop fluorescent probes for HS detection with high sensitivity and good selectivity. Herein, a novel NIR fluorescent probe NDCM-2 based on the dicyanoisophorone derivative was designed and synthesized by employing ortho-aldehyde assisted thiolysis of 2,4-dinitrophenyl (DNP) ether as the sensing strategy to achieve highly specific HS detection in living systems. The studies demonstrated that probe NDCM-2 exhibited excellent sensing performance toward HS with 160-fold NIR fluorescence enhancement, a rapid response within 15 min, excellent sensitivity with a detection limit of 58.797 nM, a large Stokes shift of 170 nm and good selectivity. In light of these unique properties, NDCM-2 has been successfully applied for the fluorescence imaging of HS in biological systems (living cells, tissues and mice), demonstrating that it would be an effective tool for HS detection in living systems.