Induced supramolecular chirality in nanostructured materials: Ionic self-assembly of perylene-chiral surfactant complexes

The synthesis and characterization of two liquid-crystalline ionically self-assembled (ISA) materials obtained by the complexation of an anionic perylene bisimide dye with cationic chiral surfactants is described for the first time. The influence of the chiral nature of the surfactants on the supramolecular organization of the resulting ISA materials is investigated. Circular dichroism (CD) spectroscopy shows that, upon complexation, the molecular chirality of the surfactants is expressed in the bisimide chromophore through the ionic linkage, clearly indicating that the surfactants act as structure-inducing moieties within the superstructures in both solution and the solid state. In solution, the complexes form left-handed helically stacked architectures. In the solid state, both systems are highly ordered and exhibit lamellar morphologies. The well-defined structures presented here are the first examples of ISA materials that show supramolecular chirality.