Taking advantage of self-assembled capacity of squaramides to form stable alcogels

Squaramides are intriguing molecular structures intensively employed in the last decade as organocatalysts. That is why they entered to be part of the research focuses of H-OCA, dedicated -as you certainly know- to the asymmetric organocatalysis field. Along to this particular application of squaramides compounds, we have broaden our scientific investigation on this chemical family. In this context , this new work have been carried out in collaboration with the research group of our collegue and friend Dr. David Díaz Díaz (Universität Regensburg), who has vast experience in the field of gels. It is well-known the self-assembled capacity of squaramides and the associated problems when they are used as catalysts. Oddly enough, this property is the core of their capacity to form supramolecular stable alcogels as it is excellently described herein. This article is part of a themed collection: Gels.

Congratulations and thanks a lot to everyone for making possible this fascinating piece of work!

“Self-assembled fibrillar networks of a multifaceted chiral squaramide: supramolecular multistimuli-responsive alcogels” Schiller, J.; Alegre-Requena, J. V.; Marqués-López, E.; Herrera, R. P.; Casanovas, J.; Alemán, C.; Díaz Díaz, D. Soft Matter, 2016, Advance Article. DOI: 10.1039/C5SM02997J

Abstract. ChiralSQ gel N,N′-disubstituted squaramide 1 has been found to undergo self-assembly in a variety of alcoholic solvents at low concentrations leading to the formation of novel nanostructured supramolecular alcogels. The gels responded to thermal, mechanical, optical and chemical stimuli. Solubility studies, gelation ability tests and computer modeling of a series of structurally related squaramides proved the existence of a unique combination of non-covalent molecular interactions and favorable hydrophobic/hydrophilic balance in 1 that drive the anisotropic growth of alcogel networks. The results have also revealed a remarkable effect of ultrasound on both the gelation kinetics and the properties of the alcogels.

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