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Issue 8, 2019
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Binding properties and supramolecular polymerization of a water-soluble resorcin[4]arene

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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

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Publication details

The article was received on 01 Feb 2019, accepted on 15 Mar 2019 and first published on 21 Mar 2019


Article type: Research Article
DOI: 10.1039/C9QO00182D
Org. Chem. Front., 2019,6, 1236-1243

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    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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