Characterization of a highly Al3+-selective fluorescence probe based on naphthalimide-Schiff base and its application to practical water samples

A new fluorescent Al3+-probe, N-allyl-4-[3,3'-((2-aminoethyl)azanediyl)-bis(N'-(2-hydroxybenzylidene)propanehy-drazide)]-1,8-naphthalimide (L), was designed and synthesized based on 1,8-naphthalimide. The probe L contains 1,8-naphthalimide moiety as the fluorophore and a Schiff base as the recognition group. The structure of L was determined by single crystal X-ray. L emission at 526 nm increased on addition of Al3+ under excitation wavelength at 350 nm. L exhibited high selectivity and sensitivity fluorescence emission towards to Al3+ in ethanol/Tris-HCl buffer solution (1:1, v/v, pH = 7.2) as compared with other tested metal ions. A good linearity with a correlation coefficient (R-2) of 0.99 was observed in the concentration range 2-10 M. The binding constant and the detection limit of L for Al3+ were calculated to 2.6 x 10(4) M-1 and 0.34 M, respectively. The results of experiments that including Job plot, ultraviolet-visible (UV-Vis) light titration, fluorescence titration, ESI-MS and H-1 NMR titration, indicated a 1:1 stoichiometric complex between L and Al3+. L was highly effective in monitoring Al3+ in real-life Yellow River and tap water samples.