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

Jiyu Tang; Kaiming Zhang; Tong Ni; Bin Xu; Binjie Hou; Xiaoqiang Liu; Weidong Jiang

doi:10.1039/d3ay01038d

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

Anal Methods. 2023 Aug 17;15(32):4021-4031. doi: 10.1039/d3ay01038d.

Authors

Jiyu Tang¹, Kaiming Zhang^{1

2}, Tong Ni¹, Bin Xu^{1

2}, Binjie Hou^{1

2}, Xiaoqiang Liu^{1

2}, Weidong Jiang^{1

2}

Affiliations

¹ School of Chemistry and Environmental Engineering, Sichuan University of Science & Engineering, Zigong, Sichuan 643000, P. R. China. jwdxb@163.com.
² Key Laboratory of Green Catalysis of Sichuan Institute of High Education, Zigong, Sichuan 643000, P. R. China.

PMID: 37548508
DOI: 10.1039/d3ay01038d

Abstract

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.