Conformation-selective synthesis and binding properties of N-benzylhexahomotriaza-p-chlorocalix[3]trinaphthylamide

N-Benzylhexahomotriaza-p-chlorocalix[3]trinaphthylamide in partial cone conformation was selectively synthesized by appropriately controlling the steric effect during the amidation reactions of N-benzylhexahomotriaza-p-chlorocalix[3]tri-(ethyl acetate) in cone or partial cone conformations with use of 1-aminomethylnaphthalene. The conformation was confirmed by H-1, C-13, and D-2 NMR and X-ray single-crystal analysis. Analyses of the complexes revealed that recognition is strongly affected by Cd2+, Pb2+, and F- ions.