In an effort to produce the tetrahedrally coordinated, catalytically active zinc center, three families of tris(2-pyridyl)methanol derivatives were synthesized and characterized. Zinc binding studies revealed that the binding behaviors of the ligands depended on the steric and electronic properties of the substituents on the pyridyl rings, as well as the functional group on the tertiary alcohol. A novel tris-pyridyl macrocyclic receptor was synthesized. The receptor possesses both hydrogen bond donors and acceptors. NMR titration experiments revealed that the receptor simultaneously bound both ammonium cation and the counter anion. The counter anion significantly influences the association between the receptor and the ammonium cation. Chiral ditopic macrocycles, which enantioselectively bind chiral ammonium cations, have also been synthesized. Their enantioselective binding properties, as well as the ditopic recognition properties were investigated