Molecular engineering of an efficient iminocoumarin-based probe for practical sensing applications

Thiophenols are important synthetic intermediates that are also primary pollutants. So, it is of great importance to develop highly sensitive and selective approaches for the detection of thiophenols in practical samples and living systems. Herein, an efficacious high-throughput strategy (benzopyran ring-opening reaction with iminocoumarins and alkylating reagents), was developed for the synthesis of fluorescent probes. The selected thiophenol-specific probe IminoC1 showed remarkable sensing performance with a 320-fold fluorescence enhancement, good detection limit of 31 nM, and high selectivity over common biothiols. Moreover, the probe IminoC1 was successfully applied for the determination of thiophenols in water samples and the visualization of thiophenols in living cells, which pointed to its strong potential for practical sensing applications. Facile preparation of iminocoumarin probe for thiophenol in water samples and living cells. [Display omitted] •A benzopyran ring-opening reaction of iminocoumarins to prepare probe IminoC1.•IminoC1 showed 320-fold fluorescent enhancement to thiophenol with high selectivity.•IminoC1 was successfully applied for sensing thiophenols in water samples and living cells.