Abstract
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.
Original language | English |
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Pages (from-to) | 1337-1341 |
Number of pages | 5 |
Journal | Angewandte Chemie - International Edition |
Volume | 57 |
Issue number | 5 |
DOIs | |
Publication status | Published - 2018 Jan 26 |
Externally published | Yes |
Keywords
- arenes
- corannulenes
- helicenes
- polycycles
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)