Atmospheric water triggers supramolecular gel formation of novel low molecular weight maslinic and oleanolic triterpenic derivatives
Metadatos
Mostrar el registro completo del ítemEditorial
RSC
Fecha
2019Referencia bibliográfica
Mater. Chem. Front., 2019, 3, 2637-2646
Patrocinador
Departamento de Química OrgánicaResumen
Pentacyclic triterpenes have a rigid lipophilic backbone decorated with polar functional groups such as
hydroxyl, carbonyl and carboxyl, which make them attractive natural amphiphiles. The ability of this type
of compound to self-assemble into complex nanostructures has recently gained interest due in part to
the abundant existence of renewable feedstocks. Herein, we present two new maslinic and oleanolic
triterpene pentacyclic derivatives that have the ability to self-assemble into long fibers giving rise to
homogeneous gels. Quite remarkably, these molecules are able to form gels by slowly capturing
atmospheric water from their DMSO and DMF solutions. To the best of our knowledge, this mechanism
of gel formation has not been previously reported for other LMWGs and highlights the versatility of
these compounds to form gels as a response to different external stimuli. The micro- and macroscopic
properties of the resulting gels have been studied in detail by TEM, SEM, NMR, VCD, FTIR, XRD and
rheology. We have demonstrated that gels prepared by capturing atmospheric water in DMSO are more
homogeneous and stiffer than those obtained by direct addition of water to the organic solution.