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

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 he...

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Bibliographic Details
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
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Summary: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.
ISSN:2052-4110
2052-4110
DOI:10.1039/c9qo00182d