Mitochondria-Targeted Fluorescent Turn-On Probe for Rapid Detection of Bisulfite/Sulfite in Water and Food Samples

Bisulfite (HSO₃^-)/Sulfite (SO₃^2-) is widely used as a food additive, but excessive use often leads to serious consequences, so the detection of HSO₃^-/SO₃^2- is of great importance. In this paper, a novel 1,4-diethylpiperazine-modified coumarin-benzopyran derivative (probe QLP) has been synthesized and characterized. In PBS (10 mM, pH = 7.4), QLP displays good selectivity and is sensitive for HSO₃^-/SO₃^2- over various analytes with fluorescent "OFF-ON" rapid responding (2 min), long-wavelength emission (600 nm), and a detection limit of 177 nM. With the treatment of HSO₃^-/SO₃^2-, the color of the QLP solution obviously changes from blue-green to yellow, and the fluorescent color of QLP changes from colorless to amaranth. The fluorescence-enhanced mechanism is qualitatively evaluated by density functional theory calculations using the CAM-B3LYP/6-31G (d) method, which reveals that the photoinduced electron transfer leads to the fluorescence emission of the QLP-SO₃H adduct. Importantly, nontoxic QLP can be used to detect HSO₃^-/SO₃^2- in sugar, natural water samples, and living cells and localized to the mitochondria and monitor the mitochondrial HSO₃^-/SO₃^2- level.