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Chiral Assembly Preferences and Directing Effects in Supramolecular Two-Component Organogels

Department of Chemistry, University of York, Heslington, York YO10 5DD, UK
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Received: 12 March 2018 / Revised: 23 March 2018 / Accepted: 25 March 2018 / Published: 29 March 2018
(This article belongs to the Special Issue Supramolecular Gels)
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Abstract

The impact of chirality on the self-assembly of supramolecular gels is of considerable importance, as molecular-scale programming can be translated into nanostructuring and ultimately affect macroscopic performance. This paper explores the effect of chirality on the assembly of two-component gels comprised of a second-generation dendritic lysine peptide acid, containing three chiral centres, and an amine. This combination forms an acid–amine complex that assembles into nanofibres through peptide-peptide hydrogen bonds, leading to organogels. With achiral amines, a racemic mixture of l,l,l and d,d,d dendritic peptide acids surprisingly forms the best gels—more commonly, mixing enantiomers suppresses gelation. Thermodynamic studies demonstrate that depending on the amine, the greater stability of heterochiral gels can either be entropically or enthalpically driven. With amines possessing “R” chirality, the l,l,l peptide acid consistently forms more effective gels than its d,d,d analogue. Furthermore, in mixed gels, l,l,l sometimes imposes its assembly preference onto d,d,d. In summary, this paper demonstrates a rare example in which heterochiral gels are preferred, and also explores directing effects when each component in a two-component gel is chiral. View Full-Text
Keywords: chirality; organogel; peptide; self-assembly; two-component chirality; organogel; peptide; self-assembly; two-component
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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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Edwards, W.; Smith, D.K. Chiral Assembly Preferences and Directing Effects in Supramolecular Two-Component Organogels. Gels 2018, 4, 31.

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