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Issue 16, 2011
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Influence of chirality on the modes of self-assembly of 12-hydroxystearic acid in molecular gels of mineral oil

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Abstract

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.

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

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Supplementary files

Article information


Submitted
25 Apr 2011
Accepted
09 Jun 2011
First published
06 Jul 2011

Soft Matter, 2011,7, 7359-7365
Article type
Paper

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

D. A. S. Grahame, C. Olauson, R. S. H. Lam, T. Pedersen, F. Borondics, S. Abraham, R. G. Weiss and M. A. Rogers, Soft Matter, 2011, 7, 7359
DOI: 10.1039/C1SM05757J

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