Issue 8, 2019

Binding properties and supramolecular polymerization of a water-soluble resorcin[4]arene

Abstract

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 1, 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 1 is also a good host for complexing anions and cations of any added salt. In combination therefore, host 1 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.

Graphical abstract: Binding properties and supramolecular polymerization of a water-soluble resorcin[4]arene

Supplementary files

Article information

Article type
Research Article
Submitted
01 feb 2019
Accepted
15 mar 2019
First published
21 mar 2019

Org. Chem. Front., 2019,6, 1236-1243

Binding properties and supramolecular polymerization of a water-soluble resorcin[4]arene

J. H. Jordan, A. Wishard, J. T. Mague and B. C. Gibb, Org. Chem. Front., 2019, 6, 1236 DOI: 10.1039/C9QO00182D

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