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Synthesis and Gelling Abilities of Polyfunctional Cyclohexane-1,2-dicarboxylic Acid Bisamides: Influence of the Hydroxyl Groups

1
Department de Química, Universitat Autònoma de Barcelona, 08193 Cerdanyola del Vallès, Barcelona, Spain
2
CIQUS (Centro Singular de Investigación en Química Biológica y Materiales Moleculares), Departamento de Química Orgánica Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain
3
The Hamburg Center for Ultrafast Imaging (CUI), Luruper Chaussee 149, 22761 Hamburg, Germany
*
Authors to whom correspondence should be addressed.
Molecules 2019, 24(2), 352; https://doi.org/10.3390/molecules24020352
Received: 8 January 2019 / Revised: 16 January 2019 / Accepted: 18 January 2019 / Published: 19 January 2019
(This article belongs to the Section Organic Chemistry)
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Abstract

New enantiomerically pure C16-alkyl diamides derived from trihydroxy cyclohexane-1,2-dicarboxylic acid have been synthesized from (−)-shikimic acid. The hydroxyl groups in these compounds are free or, alternatively, they present full or partial protection. Their gelling abilities towards several solvents have been tested and rationalized by means of the combined use of Hansen solubility parameters, scanning electron microscopy (SEM), and circular dichroism (CD), as well as computational calculations. All the results allowed us to account for the capability of each type of organogelator to interact with different solvents and for the main mode of aggregation. Thus, compounds with fully protected hydroxyl groups are good organogelators for methanol and ethanol. In contrast, a related compound bearing three free hydroxyl groups is insoluble in water and polar solvents including alcohols but it is able to gelate some low-polarity solvents. This last behavior can be justified by strong hydrogen bonding between molecules of organogelator, which competes advantageously with polar solvent interactions. As an intermediate case, an organogelator with two free hydroxyl groups presents an ambivalent ability to gelate both apolar and polar solvents by means of two aggregation patterns. These involve hydrogen bonding interactions of the unprotected hydroxyl groups in apolar solvents and intermolecular interactions between amide groups in polar ones. View Full-Text
Keywords: polyfunctional cycloalkane bisamides; organogelator; self-assembly; chirality; hydrogen bonds polyfunctional cycloalkane bisamides; organogelator; self-assembly; chirality; hydrogen bonds
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Pi-Boleda, B.; Campos, M.; Sans, M.; Basavilbaso, A.; Illa, O.; Branchadell, V.; Estévez, J.C.; Ortuño, R.M. Synthesis and Gelling Abilities of Polyfunctional Cyclohexane-1,2-dicarboxylic Acid Bisamides: Influence of the Hydroxyl Groups. Molecules 2019, 24, 352.

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