Fluorescence and metal-ion recognition properties of acetylacetone-based ligands

A new acetylacetone-based ligand (Ligand 1) bearing pyrene unit was synthesized and the fluorescence and metal-ion recognition properties were investigated in the presence of a different metal ion in acetonitrile solution. The fluorescence emission of Ligand 1 was strongly quenched by complexation with Cu2+ while no significant change was observed in the presence of other metal ions. The metal-ion selectivity changed from Cu2+ to Ni2+ when glycine moiety (–NH–CH2–CO–) was introduced into Ligand 1 as spacer. This result implies that hydrogen-bonding induced by the glycine moiety affects the binding ability of ligands to metal ions, resulting in change of the metal-ion selectivity.