Thiols, such as cysteine (Cys), homocysteine (Hcy), glutathione (GSH), hydrogen sulfide (HS), and thiophenol are metabolically correlated with each other via redox reactions. As a result of the similarity of chemical properties between Cys, Hcy, GSH, HS, and thiophenol, it is very challenging to develop an effective methodology to differentiate them. In this work, a triple-emission fluorescent probe, NCQ, was reported for the simultaneous detection of Cys/Hcy, GSH/HS, and thiophenol with high sensitivity and selectivity. The solution of NCQ displayed distinct fluorescent signals toward Cys/Hcy, GSH/HS, and thiophenol: blue and green for Cys/Hcy, blue for GSH/HS, blue and red for thiophenol. Through the blue-green-red emission color combination, Cys/Hcy, GSH/HS, and thiophenol could be discriminatively detected in solution and in living cells.

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A red-emitting fluorescent probe was developed for the sensitive and selective detection of HS. Upon treatment with HS, this probe exhibited a remarkable fluorescence enhancement (10 fold) with a large Stokes shift (125 nm). The detection limit of this probe was as low as 5.7 nM based on S/N = 3. The application of this probe in the detection of intracellular HS in living cells is successfully demonstrated.

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