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 ¹H, ¹³C, and 2D NMR and X-ray single-crystal analysis. Analyses of the complexes revealed that recognition is strongly affected by Cd²⁺, Pb²⁺, and F⁻ ions.