Deoxypyridinoline‐bioinspired supramolecular antibacterial salts with a C—H⋯O hydrogen‐bonded tetrameric host to construct the helical scaffold and sheet structures: The importance of rotational flexibility, anion shapes, and robust C—H⋯O hydrogen bonding

• Published in: Journal of the Chinese Chemical Society (Taipei) Vol. 67; no. 1; pp. 88 - 93
• Main Authors: Hung, Hui‐Yu, Hsu, Ching‐I, Wu, Che‐Kai, Wen, Hsin‐Yi, Lee, Kwang‐Ming
• Format: Journal Article
• Language: English
• Published: Weinheim Wiley‐VCH Verlag GmbH & Co. KGaA 01.01.2020; Wiley Subscription Services, Inc
• Subjects: Anions; crystal engineering; C—H⋯O hydrogen bonding; Flexibility; Hexanoic acid; Hydrogen; Hydrogen bonding; Robustness; Scaffolds; supramolecular structures
• ISSN: 0009-4536; 2192-6549
• DOI: 10.1002/jccs.201900190

A new flexible hydrogen‐bonded supramolecular host based on two deoxypyridinoline‐bioinspired 6‐hexanoic acid‐substituted 3‐hydroxypyridinium cations that adopt the twist and planar conformations and construct the orthogonal single helical scaffold and sheet structures with the triangular NO3− and spherical Br− guest anions, respectively. The results demonstrated not only the importance of rotational flexibility, anion shapes, and robust C—H⋯O hydrogen bonding, but also the good antibacterial activity with the potential antibacterial application. A novel orthogonal single‐helix scaffold and a sheet‐like supramolecular host‐guest structures were formed by deoxypyridinoline‐bioinspired 6‐hexanolic acid‐substituted 3‐hydroxypyridinium nitriate (1) and brimide (2), and were controlled by the rotational flexibility of 6‐hexanolic acid and the shapes of nitrate and bromide