Multiple fluorescence and hydrogen peroxide-responsive properties of novel triphenylamine-benzothiazole derivatives.

A novel fluorescent dye molecule - triphenylamine (TPA)-benzothiazole (BZT) - based on excited state intramolecular proton transfer (ESIPT) was prepared by the Suzuki coupling reaction. The photophysical property assay indicates that BZT-TPA appeared in distinguishable colors in mixed solvents with different water contents. Moreover, BZT-TPA exhibited observable AIE behavior. On this basis, a fluorescent probe BZT-TPA-BO was synthesized for detecting HO. This probe molecule was found to have excellent selectivity, rapid response, and good linear relationship ( = 0.989) for detecting HO in aqueous medium. Through DFT calculation, fluorescence spectrum, nuclear magnetic titration and HR-MS, the mechanism of recognition of HO by the probe BZT-TPA-BO is proposed. In addition, the probe BZT-TPA-BO to some extent exhibited better performance for detecting exogenous HO in HeLa cells.