Dual Detection of Temperature And Chiral Amino Acid Using Triphenylamine‐Based Fluorescent Probes

Accuracy measurement of temperature is important in day-to-day life and scientific research. Chiral amino acids play an irreplaceable role in medicine, biochemistry, and other fields; however, the polarity solvents do easily disturb hydrogen bond formation between chiral amino acids and fluorescence probe. Herein, a fluorescent probe Tap-S, using triphenylamine as fluorophore, is synthesized for dual detection of temperature and enantiomers of chiral amino acids in polarity aqueous solution. The fluorescence emission of Tap-S to the temperature has a good response in the mixed solvent of methanol and glycerin over a wide temperature range (−45 to 50 °C). The gradient thermosensitivity, accuracy and reversibility of Tap-S to the temperature in our strategy are achieved. Tap-S can emit yellow fluorescence in the high-viscosity mixed solution. By taking advantage of the viscosity measurement, the restricted intramolecular rotation mechanism of Tap-S's fluorescence emission was effectively clarified. Furthermore, the potential use of Tap-S to selective detect L-phenylalanine of chiral amino acids has been successfully executed in the polarity aqueous solution at the room temperature (25 °C). The complex of Tap-S and L-phenylalanine can inhibit the rotation of the single bond of Tap-S inducing the fluorescence emission. This work provides a novel strategy for the studies on not only the detection of temperature but also the enantiomers of chiral amino acids.