Control of Helical Handedness in Self-assembled Graphitic Nanotubes

  Self-assembly of a Gemini-shaped, chiral amphiphilic hexa-peri- hexabenzocoronene having two chiral oxyalkylene side chains, along with two lipophilic side chains, yields graphitic nanotubes with one-handed helical chirality. The nanotubes with right- and left-handed helical senses were obtained from the (S)- and (R)-enantiomers of the amphiphile, respectively, due to an efficient translation of point chirality into supramolecular helical chirality. In sharp contrast, a hexabenzocoronene amphiphile with chiral lipophilic side chains did not form nanotubular assemblies. The present work demonstrates the majority rule in noncovalent systems and also may provide a synthetic strategy toward realization of molecular solenoids.