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

• Published in: Organic & biomolecular chemistry 2022-11, Vol.2 (46), p.923-951
• Main Authors: Liu, Zejiang, Zhou, Yidan, Yuan, Lihua
• Format: Article
• Language: English
• Subjects: Aromatic compounds; Catalysis; Chemical bonds; Chemical synthesis; Cyclic compounds; Hydrogen bonding; Hydrogen bonds; Ion channels; Molecular machines; Self-assembly; Supramolecular compounds
• ISSN: 1477-0520; 1477-0539
• DOI: 10.1039/d2ob01263d

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. This review compiles the synthesis, properties and functions of hydrogen-bonded aromatic amide macrocycles and derivatives. Special attention is paid to their intramolecular hydrogen bonding motifs, which provide a paradigm for molecular design.