A two photon fluorescent probe for highly selective detection and endogenous imaging of hydrogen sulfide

Hydrogen sulfide (H₂S), one of redox-active sulfur species, is known as a signaling molecule and an antioxidant in biological tissues to maintain cellular functions. The development of selective and sensitive H₂S detection is important to understand the role of H₂S in vivo. Herein, a new two-photon probe NNE was developed to detect hydrogen sulfide using 6-acetyl-N-methyl-2-naphthylamine with an attachment of 7-nitrobenzo-oxadiazole. The probe NNE exhibits high selectivity towards hydrogen sulfide over other anions. Nucleophilic substitution of H₂S leads to a turn-on response with 28-fold enhancement in quantum yield (from 0.004 to 0.117). NNE shows a high sensitivity towards hydrogen sulfide with an extremely low detection limit at 6.8 nM. Furthermore, the probe NNE exhibits two-photon excited fluorescence, making it a suitable probe for monitoring H₂S distribution in live cells and tissues without background fluorescence interference.