A Novel Triphenylamine-Based Flavonoid Fluorescent Probe with High Selectivity for Uranyl in Acid and High Water Systems

Abstract

Developing a fluorescent probe for UO₂²⁺, which is resistant to interference from other ions such as Cu²⁺ and can be applied in acidic and high-water systems, has been a major challenge. In this study, a "turn-off" fluorescent probe for triamine-modified flavonoid derivatives, 2-triphenylamine-3-hydroxy-4H-chromen-4-one (abbreviated to HTPAF), was synthesized. In the solvent system of dimethyl sulfoxide:H₂O (abbreviated to DMSO:H₂O) (v/v = 5:95 pH = 4.5), the HTPAF solution was excited with 364 nm light and showed a strong fluorescence emission peak at 474 nm with a Stokes shift of 110 nm. After the addition of UO₂²⁺, the fluorescence at 474 nm was quenched. More importantly, there was no interference in the presence of metal ions (Pb²⁺, Cd²⁺, Cr³⁺, Fe³⁺, Co²⁺, Th⁴⁺, La³⁺, etc.), especially Cu²⁺ and Al³⁺. It is worth noting that the theoretical model for the binding of UO₂²⁺ to HTPAF was derived by more detailed density functional theory (DFT) calculations in this study, while the coordination mode was further verified using HRMS, FT-IR and ¹HNMR, demonstrating a coordination ratio of 1:2. In addition, the corresponding photo-induced electron transfer (PET) fluorescence quenching mechanism was also proposed.

Keywords: UO22+; flavonoid; fluorescent probe; triphenylamine; turn off.