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Multiple fluorescence and hydrogen peroxide-responsive properties of novel triphenylamine-benzothiazole derivatives. 2023

Jiyu Tang, and Kaiming Zhang, and Tong Ni, and Bin Xu, and Binjie Hou, and Xiaoqiang Liu, and Weidong Jiang
School of Chemistry and Environmental Engineering, Sichuan University of Science & Engineering, Zigong, Sichuan 643000, P. R. China. jwdxb@163.com.

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 H2O2. This probe molecule was found to have excellent selectivity, rapid response, and good linear relationship (R2 = 0.989) for detecting H2O2 in aqueous medium. Through DFT calculation, fluorescence spectrum, nuclear magnetic titration and HR-MS, the mechanism of recognition of H2O2 by the probe BZT-TPA-BO is proposed. In addition, the probe BZT-TPA-BO to some extent exhibited better performance for detecting exogenous H2O2 in HeLa cells.

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