Expression of supramolecular chirality in aggregates of chiral amide-containing surfactants

The aggregation behaviour of a series of chiral amide-containing surfactants 1-5 is studied in order to assess the structural requirements for the generation of supramolecular chirality. It is found that the presence of hydrogen-bonding moieties (i.e., amide groups) in the molecules alone is not sufficient for the formation of chiral aggregates and that the expression of chirality at a higher level, for example in the form of helical structures, strongly depends on the head-group organisation of the surfactant molecules. By changing the intermolecular interactions between the molecules, for example by pH variation or metal-ion complexation, this headgroup organisation can be tuned in such a way that supramolecular expression of chirality is induced or altered in the aggregates.