RT Journal Article
T1 Synthesis and Gelling Abilities of Polyfunctional Cyclohexane-1,2-dicarboxylic Acid Bisamides: Influence of the Hydroxyl Groups
A1 Pi-Boleda, Bernat
A1 Campos Torrado, María
A1 Sans, Marta
A1 Basavilbaso González, Antonio
A1 Illa, Ona
A1 Branchadell, Vicenç
A1 Estévez Cabanas, Juan Carlos
A1 Ortuño, Rosa M.
K1 Polyfunctional cycloalkane bisamides
K1 Organogelator
K1 Self-assembly
K1 Chirality
K1 Hydrogen bonds
AB 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
PB MDPI
SN 1420-3049
YR 2019
FD 2019
LK http://hdl.handle.net/10347/21102
UL http://hdl.handle.net/10347/21102
LA eng
NO 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
NO Financial support from Spanish Ministry of Science and Innovation (Project CTQ2009-08490) and MINECO (grant CTQ2016-77978-R), the Xunta de Galicia (Project CN2011/037 and Project GRC2014/040), Galchimia S.A., the Xunta de Galicia (Centro singular de investigación de Galicia accreditation 2016–2019, ED431G/09) and the European Union (European Regional Development Fund-ERDF)
DS Minerva
RD 24 abr 2026