Synthesis and gelling abilities of polyfunctional cyclohexane-1,2-dicarboxylic acid bisamides : Influence of the hydroxyl groups
Pi i Boleda, Bernat (Universitat Autònoma de Barcelona. Departament de Química)
Campos, María (Universidade de Santiago de Compostela. Centro Singular de Investigación en Química Biológica y Materiales Moleculares)
Sans Valls, Marta (Universitat Autònoma de Barcelona. Departament de Química)
Basavilbaso, Antonio (Universidade de Santiago de Compostela. Centro Singular de Investigación en Química Biológica y Materiales Moleculares)
Illa, Ona (Universitat Autònoma de Barcelona. Departament de Química)
Branchadell Gallo, Vicenç (Universitat Autònoma de Barcelona. Departament de Química)
Estévez, Juan Carlos (Universidade de Santiago de Compostela. Centro Singular de Investigación en Química Biológica y Materiales Moleculares)
Ortuño Mingarro, Rosa María (Universitat Autònoma de Barcelona. Departament de Química)

Data:	2019
Resum:	New enantiomerically pure C-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.
Ajuts:	Ministerio de Ciencia e Innovación CTQ2009-08490 Ministerio de Economía y Competitividad CTQ2016-77978-R
Drets:	Aquest document està subjecte a una llicència d'ús Creative Commons. Es permet la reproducció total o parcial, la distribució, la comunicació pública de l'obra i la creació d'obres derivades, fins i tot amb finalitats comercials, sempre i quan es reconegui l'autoria de l'obra original.
Llengua:	Anglès
Document:	Article ; recerca ; Versió publicada
Matèria:	Polyfunctional cycloalkane bisamides ; Organogelator ; Self-assembly ; Chirality ; Hydrogen bonds
Publicat a:	Molecules, Vol. 24, Issue 2 (January 2019) , art. 352, ISSN 1420-3049

DOI: 10.3390/molecules24020352
PMID: 30669453

17 p, 3.4 MB

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