Hydrogen-bonded aromatic amide macrocycles: synthesis, properties and functions

Org Biomol Chem. 2022 Nov 30;20(46):9023-9051. doi: 10.1039/d2ob01263d.

Abstract

As a classic example of nearly planar cyclic compounds, hydrogen-bonded aromatic amide (H-bonded aramide) macrocycles, consisting of consecutive intramolecular hydrogen bonds and aromatic residues, receive considerable research attention due to their rich host-guest chemistry. This review provides a detailed summary of the synthesis, properties and functions of H-bonded aramide macrocycles and their derivatives. Herein, the constitutional patterns of these macrocycles are divided into two subcategories: interior hydrogen bonding motifs and exterior hydrogen bonding motifs. Based on these two motifs, we summarize the facile synthesis, self-assembly, host-guest interaction complexation of H-bonded aramide macrocycles and the resulting applications such as molecular recognition, artificial ion channels, soft materials, supramolecular catalysis, and artificial molecular machines. The development of H-bonded aramide macrocycles is still in its infancy, although a considerable number of examples have been reported. We hope that this review will provide useful information and unlock new opportunities in this field.

Publication types

  • Review
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides* / chemistry
  • Hydrogen
  • Hydrogen Bonding
  • Macrocyclic Compounds* / chemistry
  • Molecular Structure

Substances

  • Amides
  • Macrocyclic Compounds
  • Hydrogen