A simple Schiff base as dual-responsive fluorescent sensor for bioimaging recognition of Zn2+ and Al3+ in living cells

Abstract

A simple Schiff base fluorescent sensor (BDNOL) was synthesized from the reaction of picolinohydrazide and 4-(diethylamino)salicylaldehyde, and developed for selective detection of Al³⁺ and Zn²⁺. This non-fluorescent sensor displayed obvious fluorescence enhancement after binding to Al³⁺/Zn²⁺ ions with high sensitivity and selectivity, accompanied by obvious fluorescence emission enhancement (504 nm for Al³⁺ and 575 nm for Zn²⁺). The detection limits were found to be 8.30 × 10⁻⁸ M for Al³⁺ and 1.24 × 10⁻⁷ M for Zn²⁺. The binding mechanisms between BDNOL and Al³⁺/Zn²⁺ ions were supported by ¹H NMR and HR-MS analysis, and a density functional theory (DFT) study. The sensing behavior was also studied with molecular logic functions of OR, AND, and NOT gates. Furthermore, the fluorescent sensor was successfully used to recognize Al³⁺ and Zn²⁺ in living cells, suggesting that this simple biosensor has great potential in biological imaging applications.