Synthesis of a new macrobicyclic ligand and investigation of its metal-ion binding properties

This study describes the synthesis, structural characterization of a new macrobicyclic ligand and its use in metal cation extraction. The structures of new compounds were characterized by a combination of elemental analysis and 1H NMR, 13C NMR, IR and MS spectral data. Solvent extraction experiments were performed in order to determine the extraction behavior of new macrobicyclic ligand towards selected metal cations. Two different organic solvents, dichloromethane and chloroform, were tested to reveal extraction efficiency. Selective extraction of heavy metals and precious metal is highly demanded due to their toxicity and commercial importance. From the experimental results, macrocyclic ligand (8) is very effective and selective for Ag+ and Hg2+ cations, whereas compounds (9) and (10) show good extraction behavior without selectivity towards Ag+cation. The highest Ag+ extraction behavior among the tested ligands in both organic solvents was observed for macrobicyclic ligand (10). Macrobicycle (10) demonstrated remarkable affinity towards the Ag+ ion by 96.7% and 96.9% to the dichloromethane and chloroform phase, respectively.