Influence of chirality on the modes of self-assembly of 12-hydroxystearic acid in molecular gels of mineral oil

The gelating abilities of enantiopure, racemic, and different enantio-enriched mixtures of 12-hydroxystearic acid (12HSA) have been compared in order to clarify conflicting reports in the literature (1) concerning their ability to gelate organic liquids. Less than 1.0 wt % of optically pure (D)-12HS...

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Published inSoft matter Vol. 7; no. 16; pp. 7359 - 7365
Main Authors Grahame, Douglas A. S., Olauson, Caitlin, Lam, Ricky S. H., Pedersen, Tor, Borondics, Ferenc, Abraham, Shibu, Weiss, Richard G., Rogers, Michael A.
Format Journal Article
LanguageEnglish
Published 01.01.2011
Subjects
Chirality
Crystals
Dimers
Minerals
Networks
Nucleation
Percolation
Self assembly
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Summary:The gelating abilities of enantiopure, racemic, and different enantio-enriched mixtures of 12-hydroxystearic acid (12HSA) have been compared in order to clarify conflicting reports in the literature (1) concerning their ability to gelate organic liquids. Less than 1.0 wt % of optically pure (D)-12HSA was found to gelate mineral oil. The gel matrix was comprised of high aspect ratio fibers in which the 12HSA molecules were organized as head-to-head dimers and the 12-hydroxyl groups formed an H-bonding network along the axis transverse to the longitudinal growth. Below 2 wt %, racemic 12HSA in mineral oil did not reach the percolation threshold. Its organogels were comprised of platelet-like crystals with a molecular arrangement of single, in-plane, hydrogen-bonded acyclic dimers that prevent longitudinal growth and limit the ability of the polar groups to phase separate during nucleation.
Bibliography:ObjectType-Article-2
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ISSN:1744-683X
1744-6848
DOI:10.1039/c1sm05757j