What is it about?

Resorcinarenes are host molecules that have been shown to dimerize in a head-to-head fashion or form much larger hexameric assemblies. However, they are not typically soluble in water. Here we describe how a water-soluble resorcinarene, with positively charged pendent groups, assembles in water to form head-to-tail chains of molecules. 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 complimentary positive charge of the pendent groups of a second resorcinarene. Alternatively, the resorcinarene may also form complexes with anions and cations of any added salt. Thus this host is shown to possess a rich repertoire of properties that is dependent on the nature of the solution (i.e. the salts, pH, and concentration of the host).

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Why is it important?

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. These findings provide new information about controlling the self-assembly of resorcinarenes in water.

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This page is a summary of: Binding properties and supramolecular polymerization of a water-soluble resorcin[4]arene, Organic Chemistry Frontiers, January 2019, Royal Society of Chemistry, DOI: 10.1039/c9qo00182d.
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