H-Bonding-Assisted One-Pot Macrocyclization for Rapid Construction of H-Bonded Macrocyclic Aromatic Foldamers

Abstract

The study of macrocycles has crossed many disciplines such as chemistry, physics, biology, medicine, and engineering with many research areas concentrating on specific and selective molecular recognition, self-organization and its already demonstrated, and other promising applications. Compared to traditional strategies to synthesize macrocycles with widely ranging structures using such as templated cyclization or dynamic covalent bond formation, the use of multiple-center intramolecular H-bonds for the efficient one-pot H-bonding-assisted construction of macrocycles of varying structures and functions is among the newest and the most noteworthy additions to the toolbox for macrocycle synthesis. This strategy has allowed the creation of sizable interior cavities of as small as 1.4 A and as large as 15 A in radius in these H-bonded macrocycles with a number of them expressing tailor-made functions. This chapter summarizes the recent works on such “greener” syntheses of H-bonded macrocycles which help to create a whole new dimension of scientific research, markedly expanding both the structural and functional repertoires of shape-persistent macrocycles that offer a new bottom-up strategy for constructing functional architectures and materials.