2-Vinylfuran substituted BODIPY H2S fluorescent turn on probe based on hydrolysis of furfural and nucleophilic addition of double bond

[Display omitted] •H2S causes hydrolysis of the furan ring while nucleophilic addition occurs on the double bond of vinylfuran.•The addition of H2S causes the strong fluorescence emission.•BODIPY-vinylfuran is highly responsive to both endogenous and exogenous H2S.•BODIPY-vinylfuran has good selectivity, high sensitivity, low detection limit and real-time detection. In this work, a fluorescent H2S turn on probe BODIPY-vinylfuran has been synthesized by reaction of 8-methyl-BODIPY with functional group 5-methylfuranal. When H2S is present, the furan ring is hydrolyzed and ring-opened, and H2S further undergoes a nucleophilic addition reaction with carbon-carbon double bond (CC) of vinylfuran, resulting in enhanced fluorescence. Due to the addition reaction of carbon-carbon double bond with H2S, the π-π conjugated structure of furan and BODIPY is destroyed, resulting in the shifting of maximum emission peak from 535 nm to 496 nm. Sensor BODIPY-vinylfuran demonstrates remarkable performance with more than 150-folds increase in fluorescence intensity, low detection limit (99.4 nM) and selectivity to H2S specificity. Furthermore, BODIPY-vinylfuran possesses low cytotoxicity and good biocompatibility. Cellular fluorescence imaging further demonstrates that BODIPY-vinylfuran is highly responsive to both endogenous and exogenous H2S.