The AIE and strong solid fluorescence of fluorescein derivatives can be realized in a simple way.

H2S is an important endogenous gasotransmitter, and its detection in living systems is of great significance. Especially, selective and sensitive near-infrared (NIR) fluorescent H2S probes with rapid response and large Stokes shift are highly desirable because of their superiority for in vivo detection. Probes with nitrobenzoxadiazole (NBD) ether as reaction sites have been well-explored recently to detect biothiols or H2S/biothiols simultaneously, rather than to detect H2S selectively. In this work, a new NBD ether-based NIR fluorescent probe was developed, which was unexpectedly found to show high selectivity for H2S over various other analytes including biothiols, making it practical for specific detection of H2S both in vitro and in vivo. Upon response to H2S, this probe showed rapid and significant turn-on NIR emission changes centered at 744 nm within 3 min, together with a remarkable large Stokes shift (166 nm) and high sensitivity (LOD: 26 nM). Moreover, imaging exogenous and endogenous H2S in living cells and rapid imaging of H2S in living mice with this probe was successfully applied with excellent performance.

To elucidate the complex role of biological H2S and study the mitochondrial damage and some related diseases, effective methods for visualization of H2S in mitochondria and in vivo are urgently needed. In this contribution, a novel near-infrared mitochondria-targetable fluorescence probe MI-H 2 S for H2S detection was developed. MI-H 2 S shows rapid detection ability for H2S in pure aqueous solution and outputs a highly selective and sensitive fluorescence-on signal at 663 nm with a large Stokes shift of 141 nm. Bioimaging experiments revealed that the probe has good mitochondrial-targeting ability and high-contrast imaging ability for detecting H2S in living systems. The probe also showed great potential in the detection of H2S during inflammation. All of the results demonstrate that MI-H 2 S can be applied as an effective probe for the visualization and study of H2S in mitochondria and in vivo.

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