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

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, toge...

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Autores principales: Basilio, Nuno, Francisco, Vitor, Garcia-Rio, Luis
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2013
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3588036/
https://www.ncbi.nlm.nih.gov/pubmed/23380960
http://dx.doi.org/10.3390/ijms14023140
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author Basilio, Nuno
Francisco, Vitor
Garcia-Rio, Luis
author_facet Basilio, Nuno
Francisco, Vitor
Garcia-Rio, Luis
author_sort Basilio, Nuno
collection PubMed
description 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.
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spelling pubmed-35880362013-03-13 Aggregation of p-Sulfonatocalixarene-Based Amphiphiles and Supra-Amphiphiles Basilio, Nuno Francisco, Vitor Garcia-Rio, Luis Int J Mol Sci Review 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. MDPI 2013-02-04 /pmc/articles/PMC3588036/ /pubmed/23380960 http://dx.doi.org/10.3390/ijms14023140 Text en © 2013 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0 This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Review
Basilio, Nuno
Francisco, Vitor
Garcia-Rio, Luis
Aggregation of p-Sulfonatocalixarene-Based Amphiphiles and Supra-Amphiphiles
title Aggregation of p-Sulfonatocalixarene-Based Amphiphiles and Supra-Amphiphiles
title_full Aggregation of p-Sulfonatocalixarene-Based Amphiphiles and Supra-Amphiphiles
title_fullStr Aggregation of p-Sulfonatocalixarene-Based Amphiphiles and Supra-Amphiphiles
title_full_unstemmed Aggregation of p-Sulfonatocalixarene-Based Amphiphiles and Supra-Amphiphiles
title_short Aggregation of p-Sulfonatocalixarene-Based Amphiphiles and Supra-Amphiphiles
title_sort aggregation of p-sulfonatocalixarene-based amphiphiles and supra-amphiphiles
topic Review
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3588036/
https://www.ncbi.nlm.nih.gov/pubmed/23380960
http://dx.doi.org/10.3390/ijms14023140
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