Water soluble and efficient amino acid Schiff base receptor for reversible fluorescence turn-on detection of Zn²⁺ ions: Quantum chemical calculations and detection of bacteria.

An amino acid Schiff base (R) capable of recognizing Zn(2+) ions selectively and sensitively in an aqueous medium was prepared and characterized. Upon addition of Zn(2+) ions, the receptor exhibits fluorescence intensity enhancements (~40 fold) at 460 nm (quantum yield, Φ=0.05 for R and Φ=0.18 for R-Zn(2+)) and can be detected by naked eye under UV light. The receptor can recognize the Zn(2+) (1.04×10(-8) M) selectively for other metal ions in the pH range of 7.5-11. The Zn(2+) chelation with R decreases the loss of energy through non-radiative transition and leads to fluorescence enhancement. The binding mode of the receptor with Zn(2+) was investigated by (1)H NMR titration and further validated by ESI-MS. The elemental color mapping and SEM/EDS analysis were also used to study the binding of R with Zn(2+). Density functional theory calculations were carried out to understand the binding mechanism. The receptor was applied as a microbial sensor for Escherichia coli and Staphylococcus aureus.