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The synthesis and structural analysis of a quintuple [6]helicene with a corannulene core is reported. The compound was synthesized from corannulene in three steps including a five-fold intramolecular direct arylation. X-ray crystallographic analysis revealed a C5-symmetric propeller-shaped structure and one-dimensional alignment in the solid state. The enantiomers of the quintuple [6]helicene were successfully separated by HPLC, and the chirality of the two fractions was identified by CD spectroscopy. A kinetic study yielded a racemization barrier of 34.2???kcal???mol-1, which is slightly lower than that of pristine [6]helicene. DFT calculations indicate a rapid bowl-to-bowl inversion of the corannulene moiety and a step-by-step chiral inversion pathway for the five [6]helicene moieties.

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Kato, K.; Segawa, Y.; Scott, L. T.; Itami, K., Angew. Chem. Int. Ed. 2018, 57, 1337-1341Contributed by Steven BacharachReposted from Computational Organic Chemistry with permissionCorannulene 1 is an interesting aromatic compound because it is nonplanar,...
Corannulene 1 is an interesting aromatic compound because it is nonplanar, having a bowl shape. [6]helicene is an interesting aromatic compound because it is nonplanar, having the shape of a helix. Kato, Segawa, Scott and Itami have joined these together to...