Benzothiazole Pyrazoline: Acid-Switchable Absorption and Fluorescence of Photoinduced Electron Transfer (PET)

Acid-responsive fluorescent compounds were prepared by introducing an ortho-hydroxyphenyl to pyrazoline with a benzothiazole backbone. These compounds demonstrated normal fluorescence photoinduced electron transfer (PET) under neutral conditions but the addition of trifluoroacetic acid showed an arctic blue fluorescence, we verified that a protonation process of nitrogen in the thiazole ring which weakened the ability of thiazole to donate electrons to the pyrazoline and changed the photoinduced electron transfer led to photoinduced electron transfer (PET), which was the mechanism of the fluorescence quenching phenomenon under strongly acidic conditions. The photophysical properties of Benzothiazole pyrazoline exhibited blue emission at 421 nm in aqueous DMSO. The blue shift in the emission was switched by acid in DMSO, showing the compound's distinct fluorescence peak at 554 nm. To investigate solvatochromism, eight different solvents were used. The red-shift emission observed in enhancing the polarity of solvents and emission in DMSO suggested the conformation of the molecule which led to the intramolecular charge transfer by color and emission changes. Furthermore, the probe was also applied using the High-performance liquid chromatography (HPLC) with a UV detector to determine the trifluoroacetic acid in water samples. Interestingly, the method was found to be linear over the range of 10.0 mu g L-1 to 250.0 mu g L-1 (0.999). Under the optimum condition, the separation of trifluoroacetic acid was achieved in 20 min with the LOD of 1.3 mu g L-1 and LOQ of 5.1 mu g L-1. This proposed method also showed satisfactory results when applied for the analysis of trifluoroacetic acid in a water sample.

Automated summary

Acid-responsive fluorescent compounds were prepared by introducing an ortho-hydroxyphenyl to pyrazoline with a benzothiazole backbone. These compounds demonstrated normal fluorescence photoinduced electron transfer (PET) under neutral conditions but showed fluorescence quenching under strongly acidic conditions. The method was also successfully applied to detect trifluoroacetic acid in water samples.