As one of the biomolecules, hydrogen sulfide (HS) has received a lot of attention. Recent studies have shown that endogenous hydrogen sulfide plays different roles in different organs in biological systems. Fluorescent probe technology has been widely adopted due to its many advantages such as low cost, simple operation, and high sensitivity. Among many probes, dicyanoisophorone fluorophore is often used in probe design for real-time detection of endogenous HS due to the large Stokes shift and long fluorescence emission wavelength. In this paper, the fluorescence sensing mechanism of dicyanoisophorone-like probe L and its product 3 with near-infrared fluorescence emission has been theoretically investigated by using theory methods. The analysis of infrared (IR) vibration spectra and reduced density gradient (RDG) showed that the hydrogen bond of the enolic structure of product 3 was significantly enhanced in the S state. The spectroscopic information revealed that the emission of NIR fluorescence originated from the keto structure of the product. Finally, potential energy curves and frontier molecular orbitals diagrams showed that the fluorescence quenching phenomenon of the probe L was attributed to the photoinduced electron transfer (PET) process, whereas the product 3 generated after the detection of HS undergoes the excited state intramolecular proton transfer (ESIPT) process.
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