The synthesis and structure of a C3-symmetric propeller-shaped polycyclic aromatic hydrocarbon that bears three seven-membered rings is reported. The synthesis was accomplished in three steps from benzo[c]naphtho[2,1-p]chrysene, including a Pd-catalyzed intramolecular C-H arylation for the formation of the seven-membered rings. The combination of the helicities (P/M) of the three seven-membered-ring moieties and three helicene moieties affords 24 possible conformers, and two relatively stable conformations were observed by 1H NMR spectroscopy.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry