A novel reversible fluorescent probe based on naphthalimide for sequential detection of aluminum (Al3+) and fluoride (F−) ions and its applications

Abstract

A new Schiff base fluorescent probe NBP derived from the one-step condensation strategy of 2-butyl-6-hydroxy-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinoline-5-carbaldehyde and N-(2-(hydrazinecarbonyl)phenyl)benzamide was synthesized and characterized. NBP exhibited high selectivity toward Al³⁺ along with naked-eye color changes and prominent fluorescence enhancement. The limit of detection (LOD) of NBP toward Al³⁺ was detected to be 80 nM. The binding ratio of NBP with Al³⁺ ions was obtained as 1 : 2 on the basis of Job's plot with the association constant K_a value of 4.22 × 10¹⁰ M^−1/2. The plausible complexation mechanism of NBP toward Al³⁺ ions was validated by the density functional theory (DFT) and IR spectrum. In addition, in situ formed “NBP + Al³⁺” could be utilized as the second sensor for selective recognition of F⁻via fluorescence quenching with a low detection limit (44 nM). Furthermore, the cell imaging experiments of probe NBP in HeLa cells have successfully demonstrated that NBP could serve as an indicator for monitoring Al³⁺ ions in living cells. On top of that, NBP could be used to prepare simple test paper strips for quickly and qualitatively detecting a trace amount of Al³⁺ ions in a visible manner.