Hydrogen-bonding-driven aromatic foldamers: their structural and functional evolution.

Abstract

This Personal Account summarizes the development of the design of hydrogen-bonding-driven aromatic foldamers and their applications in supramolecular chemistry. This account begins with a short, non-exhaustive description of the background in the study of hydrogen-bonded aromatic foldamers. The construction of foldamers from discrete aromatic residues, including amide, urea, hydrazide and 1,2,3-triazole units, is then described. In the following parts, the applications of such compact aromatic oligomers in supramolecular chemistry, including the development of acyclic receptors, the construction of hybrid helical sequences through intramolecular stacking, the promotion of the formation of covalently and noncovalently bonded macrocycles, the tuning of the mechanical properties of copolymers, and the regulation of the shuttling behavior of [2]rotaxanes and the controlled release of dye from reverse vesicles formed from them, are described. In the final part, the binding-induced folding of conformationally flexible aromatic amide oligomers and their self-binding are described.