Development and application of a novel β-diketone difluoroboron-derivatized fluorescent probe for sensitively detecting H2S

A novel colorimetric and turn-on fluorescent probe for detecting H 2 S with low detection limit and large Stokes shift. • A ‘turn-on’ fluorescent probe MCBF for detecting H 2 S was synthesized based on 4-(dimethylamino)cinnamaldehyde and myrtenal. • MCBF towards H 2 S represented excellent sensitivity, anti-interference, low detection limit, and remarkable Stokes shift. • The sensing mechanism was successfully proved by HRMS, 1 H NMR, and DFT calculation. • MCBF was well applied in quantitatively detecting endogenous H 2 S contents in red wine samples. Hydrogen sulfide{Wang, 2018 #4}{Wang, 2018 #4}{Zhong, 2020 #9} (H 2 S) is a poisonous and harmful gas molecule. Certain concentrations of H 2 S{Liu, 2021 #8} can irritate the eyes, respiratory system, and central nervous system of human beings. Therefore, it was an urgent need for highly selective, anti-interference, and sensitive detection technology for hydrogen sulfide. Herein, a novel “turn-on” fluorescent probe 1-(2-(6,6-dimethylbicyclo[3.1.1]heptyl-2-ene-2-yl))-9-(4-(dimethylaminophenyl))non-1,6,8-triene-3,5-dione boron difluoride complex ( MCBF ) was designed and synthesized for detecting H 2 S sensitively. MCBF displayed a remarkable fluorescence enhancement response to H 2 S with a large Stokes shift of 220 nm. The sensitive detection of MCBF towards H 2 S owned good selectivity, fast response time (6 min), excellent photostability, and low detection limit (0.44 μM). The sensing mechanism of MCBF towards H 2 S was well confirmed by HRMS analysis, 1 H NMR titration, and density functional theory (DFT) calculations. What’s more, probe MCBF was successfully applied to detect the contained H 2 S in red wine, which showed the potential practicability of MCBF in real samples analysis.