Ion Sensor Properties of Fluorescent Schiff Bases Carrying Dipicolylamine Groups. A Simple Spectrofluorimetric Method...

Four fluorescent Schiff bases carrying dipicolylamine groups were designed and synthesized to determine their ion sensor properties in partial aqueous solution. The corresponding amine compound and the aldehyde compounds such as 1-naphthaldehyde, 9-anthraldehyde, phenanthrene-9-carboxaldehyde and 1-pyrenecarboxaldehyde were used to prepare the new Schiff bases. The influence of many metal cations and anions on the spectroscopic properties of the ligands was investigated in ethanol-water (1:1) by means of emission spectrometry. From the spectrofluorimetric titrations, the complexation stoichiometry and complex stability constants of the ligands with Cd²⁺, Zn²⁺, Cu²⁺ and Hg²⁺ ions were determined. The ligands did not interact with the anions. However, the Schiff base derived from phenanthrene-9-carboxaldehyde showed sensitivity for Cu²⁺ among the tested metal ions. The phenanthrene-based Schiff base was used as analytical ligand for the simple and fast determination of Cu²⁺ ion in water samples. A modified standard addition method was used to eliminate matrix effect. The linear range was from 0.3 mg/L to 3.8 μg/L. Detection and quantification limits were 0.14 and 0.43 mg/L, respectively. Maximum contaminant level goal (MCLG) for copper in drinking water according to EPA is 1.3 mg/L. The proposed method has high sensitivity to determine copper in drinking waters.