Multiple fluorescence and hydrogen peroxide-responsive properties of novel triphenylamine-benzothiazole derivatives.
Jiyu TangKaiming ZhangTong NiBin XuBinjie HouXiaoqiang LiuWeidong JiangPublished in: Analytical methods : advancing methods and applications (2023)
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 H 2 O 2 . This probe molecule was found to have excellent selectivity, rapid response, and good linear relationship ( R 2 = 0.989) for detecting H 2 O 2 in aqueous medium. Through DFT calculation, fluorescence spectrum, nuclear magnetic titration and HR-MS, the mechanism of recognition of H 2 O 2 by the probe BZT-TPA-BO is proposed. In addition, the probe BZT-TPA-BO to some extent exhibited better performance for detecting exogenous H 2 O 2 in HeLa cells.
Keyphrases
- living cells
- fluorescent probe
- hydrogen peroxide
- single molecule
- quantum dots
- cell cycle arrest
- nitric oxide
- energy transfer
- induced apoptosis
- multiple sclerosis
- ms ms
- density functional theory
- electron transfer
- cell death
- drug delivery
- molecular docking
- high resolution
- cancer therapy
- molecularly imprinted
- molecular dynamics simulations