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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.

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