Hierarchical growth of chiral self-assembled structures in protic media

The location of nine chiral penta(ethylene oxide) side chains at the periph ery of a C-3-symmetrical hydrogen-bonded extended core gives rise to a ther motropic discotic liquid crystalline material that shows lyotropic phases i n polar, protic media. The molecular stacks self-assemble in a reversible a nd hierarchical fashion, and specific and subtle solvent-molecule interacti ons together with the created hydrophobic microenvironment account for an u nprecedented stabilization of a preferred handedness of the helical stacks by cooperative intermolecular interactions. The presence of either chiralit y or achirality at the supramolecular level in the stacks can be tuned by t emperature and solvent as judged from circular dichroism spectroscopy. A hi erarchical growth of the self-assembly is revealed using a variety of spect roscopic techniques and differential scanning calorimetry.