Chiral supramolecular polymers based on multiple hydrogen bonding

A variety of discotic crystalline molecules are studied that form chiral polymeric assemblies in either apolar organic solvents or water. Multiple hydrogen bonds are used to organize the molecules into a well defined helix. A preferred handedness of the helical superstructures is obtained by chiral side chains based on citronellol for assemblies in solvents like dodecane and chiral penta-ethylene glycols for assemblies in water. Sergeants-and-soldiers principles are observed, showing the cooperative character in the chiral superstructures. The stable chiral structures in water of assemblies is used to speculate on the scope and limitations of the folding of chiral synthetic polymers in water using a variety of secondary interactions.