Supramolecular crowns: a new class of cyclic hydrogen-bonded cavitands

Abstract

A novel design of highly preorganized bicyclic monomers, based on quadruple hydrogen bonding motifs, is proposed to access noncovalent cavitands with large internal volumes and interesting shapes. Selective formation of tetrameric aggregates was demonstrated and the newly obtained cyclic assemblies were fully characterized by NMR and gel permeation chromatography. The high fidelity of the aggregation process, high aggregate stability and simple synthesis of the monomer open up the way for future use of the herein reported new class of cavitands in various fields of supramolecular chemistry.