Influence of positional isomers on the macroscale and nanoscale architectures of aggregates of racemic hydroxyoctadecanoic acids in their molecular gel, dispersion, and solid states

Langmuir : the ACS Journal of Surfaces and Colloids
Shibu AbrahamMichael A Rogers

Abstract

Inter/intramolecular hydrogen bonding of a series of hydroxystearic acids (HSAs) are investigated. Self-assembly of molecular gels obtained from these fatty acids with isomeric hydroxyl groups is influenced by the position of the secondary hydroxyl group. 2-Hydroxystearic acid (2HSA) does not form a molecular dimer, as indicated by FT-IR, and growth along the secondary axis is inhibited because the secondary hydroxyl group is unable to form intermolecular H-bonds. As well, the XRD long spacing is shorter than the dimer length of hydroxystearic acid. 3-Hydroxystearic acid (3HSA) forms an acyclic dimer, and the hydroxyl groups are unable to hydrogen bond, preventing the crystal structure from growing along the secondary axis. Finally, isomers 6HSA, 8HSA, 10HSA, 12HSA, and 14HSA have similar XRD and FT-IR patterns, suggesting that these molecules all self-assemble in a similar fashion. The monomers form a carboxylic cyclic dimer, and the secondary hydroxyl group promotes growth along the secondary axis.

References

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Oct 23, 2009·Journal of Colloid and Interface Science·Anne-Laure FameauJean-Paul Douliez

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Citations

Feb 4, 2016·The Journal of Physical Chemistry. B·S VimalaUma S Hiremath
Mar 19, 2013·Journal of Colloid and Interface Science·Maria Laura Di LorenzoJohn Doran
May 6, 2015·Chemical Society Reviews·Y LanM A Rogers
Dec 18, 2013·Chemistry : a European Journal·Marta Tena-SolsonaBeatriu Escuder
May 6, 2015·ACS Applied Materials & Interfaces·Ni ChengLi Yu
Aug 9, 2013·Chemical Society Reviews·D Krishna Kumar, Jonathan W Steed
Jul 10, 2013·Langmuir : the ACS Journal of Surfaces and Colloids·Shinya Hirayama, Masahito Sano
Apr 18, 2013·Langmuir : the ACS Journal of Surfaces and Colloids·Phillip Lee, Michael A Rogers
Oct 7, 2016·Chemical Society Reviews·Christopher D Jones, Jonathan W Steed
Nov 20, 2016·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Mohan Zhang, Richard G Weiss
Aug 9, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Fioretta AsaroEnnio Zangrando
Nov 26, 2020·Gels·Dipankar GhoshKrishna K Damodaran
May 1, 2021·Gels·Pedram NasrMichael A Rogers
Jul 24, 2018·The Journal of Physical Chemistry. B·Kazuma HonmaMasahito Sano

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