A near-infrared fluorescent probe based on corrole derivative with large Stokes shift for detection of hydrogen sulfide in water and living cells

A distinct near-infrared (NIR) fluorescent probe (COR-DNBS), based on corrole derivative, was designed and synthesized for detection of hydrogen sulfide (H2S) by the photoinduced electron transfer (PET) mechanism. Probe COR-DNBS was constructed by 5,15-di(4-chlorophenyl)-10-(4-hydroxylphenyl)-corrole (COR-OH) as fluorophore and 2,4-dinitrobenzenesulfonyl ether (DNBS) as recognition site. The chemical structure of COR-DNBS was fully characterized by H-1 NMR, C-13 NMR, EA, IR and mass spectrometry. COR-DNBS showed a high selectivity and an excellent sensitivity to H2S with a detection limit of 28 nM together with a fast response (46 s). Importantly, it also exhibited a large Stokes shift (231 nm) and red emission (656 nm), which is highly desirable for bioimaging applications. The sensing mechanism was proved to be H2S triggered thiolysis reaction by 1H NMR, HRMS and the DFT calculations. In the present work, successful detection and bioimaging of H(2)Sin water and living cells was achieved. Moreover, COR-DNBS could be used as a paper test strip for monitoring and screening of H2S in environment.

Automated summary

In this study, a near-infrared fluorescent probe COR-DNBS based on corrole derivative was designed and synthesized for detection of hydrogen sulfide. The probe showed high selectivity and sensitivity, with a fast response and desirable properties for bioimaging applications.