The synthesis and structural analysis of a quintuple 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 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 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 helicene moieties.
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