Huisgen dipolar cycloaddition leads straightforwardly to new funnel complexes based on the calix[6]arene macrocycle bearing three functionalized triazoles as coordinating units at the small rim. Coordination to Zn(II) and Cu(I) cations was studied using (1)H NMR and IR spectroscopies and cyclic voltammetry. The nature of the substituents on the triazole ring affects the behavior of the ligands and their coordinating ability and controls the host-guest properties of the metal receptors for exogenous substrates. Depending on their substitution pattern but also on the metal ion and the guest ligand, the triazole-based systems behave either imidazole-like or pyridine-like. The ease of preparation and the versatility of 1,4-disubstituted-1,2,3-triazoles with tunable steric and electronic properties make them promising candidates for further applications from biology to materials.
© 2011 American Chemical Society