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Int. J. Mol. Sci. 2013, 14(2), 3140-3157;

Aggregation of p-Sulfonatocalixarene-Based Amphiphiles and Supra-Amphiphiles

Physical Chemistry Department, Center for Research in Biological Chemistry and Molecular Materials (CIQUS), University of Santiago, 15782 Santiago, Spain
Author to whom correspondence should be addressed.
Received: 30 November 2012 / Revised: 24 January 2013 / Accepted: 24 January 2013 / Published: 4 February 2013
(This article belongs to the Special Issue Molecular Self-Assembly 2012)
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p-Sulfonatocalixarenes are a special class of water soluble macrocyclic molecules made of 4-hydroxybenzenesulfonate units linked by methylene bridges. One of the main features of these compounds relies on their ability to form inclusion complexes with cationic and neutral species. This feature, together with their water solubility and apparent biological compatibility, had enabled them to emerge as one the most important host receptors in supramolecular chemistry. Attachment of hydrophobic alkyl chains to these compounds leads to the formation of macrocyclic host molecules with amphiphilic properties. Like other oligomeric surfactants, these compounds present improved performance with respect to their monomeric counterparts. In addition, they hold their recognition abilities and present several structural features that depend on the size of the macrocycle and on the length of the alkyl chain, such as preorganization, flexibility and adopted conformations, which make these molecules very interesting to study structure-aggregation relationships. Moreover, the recognition abilities of p-sulfonatocalixarenes enable them to be applied in the design of amphiphiles constructed from non-covalent, rather than covalent, bonds (supramolecular amphiphiles). In this review, we summarize the developments made on the design and synthesis of p-sulfonatocalixarenes-based surfactants, the characterization of their self-assembly properties and on how their structure affects these properties. View Full-Text
Keywords: calixarenes; surfactants; supramolecular amphiphiles; micelle; vesicle  calixarenes; surfactants; supramolecular amphiphiles; micelle; vesicle 
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Basilio, N.; Francisco, V.; Garcia-Rio, L. Aggregation of p-Sulfonatocalixarene-Based Amphiphiles and Supra-Amphiphiles. Int. J. Mol. Sci. 2013, 14, 3140-3157.

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