Configurationally stable longitudinally twisted polycyclic aromatic compounds.

Two strategies for the synthesis of configurationally stable twisted polycyclic aromatic compounds (PACs) were pursued. The first approach employed dissymmetrically positioned 1-naphthyl substituents to bias the direction of twist in highly substituted PACs. 2,3-Bis(1-naphthyl)-1,4-diphenyltriphenylene (7) was prepared, and its meso cis-dinaphthyl and enantiomeric trans-dinaphthyl isomers were resolved by preparative supercritical fluid chromatography (SFC) on chiral supports.