Consequences of conformational flexibility in hydrogen-bond-driven self-assembly processes.

We report the synthesis and self-assembly of chiral, conformationally flexible C3-symmetrical trisamides. A strong Cotton effect is observed for the supramolecular polymers in linear alkanes but not in cyclic alkanes. MD simulations suggest 2 : 1 conformations of the amides within the aggregates in both types of solvents, but a chiral bias in only linear alkanes.