Binding Properties and Supramolecular Polymerization of a Water-Soluble Resorcin[4]arene

• Published in: Organic chemistry frontiers an international journal of organic chemistry 2019-04, Vol.6 (8), p.1236-1243
• Main Authors: Jordan, Jacobs H, Wishard, Anthony, Mague, Joel T, Gibb, Bruce C
• Format: Article
• Language: English
• Subjects: Anions; Cations; Containers; Crystallography; Hydrogen bonds; Ionic strength; Organic chemistry; Polarity; Polymerization; Polymers; Properties (attributes); Pyridinium; Salts; Self-assembly; Supramolecular polymers; Tail assemblies
• ISSN: 2052-4110; 2052-4110
• DOI: 10.1039/c9qo00182d

Controlling the self-assembly of molecules in water is difficult because the small size, polarity, and hydrogen bond donating and accepting properties of water attenuate most non-covalent interactions. Here we describe how resorcinarene , with pyridinium pendent groups, assembles in water to form head-to-tail assemblies. These small supramolecular polymers form because they offer greater stabilization than any latent head-to-head assembly of resorcinarenes to form dimeric (or hexameric) containers. Instead, the resorcinarene bowl - particularly if negatively charged - is a good host for the pyridinium pendent groups of a second resorcinarene. Alternatively, resorcinarene is also a good host for complexing anions and cations of any added salt. In combination therefore, host possesses a rich repertoire of supramolecular properties that is dependent on the ionic strength and the nature of salts, pH, and the concentration of the host. These findings provide new information about controlling the self-assembly of resorcinarenes in water.