Synthesis of Substituted Trinaphthylenes via Aryne Cyclotrimerization

The first synthesis of a series of substituted trinaphthylene derivatives via a palladium-catalyzed aryne cyclotrimerization is reported. This method provides an approach for the preparation of novel disk-shaped polycyclic aromatic hydrocarbons that self-assemble via pi-pi interactions and may form columnar liquid crystal phases. Although the trinaphthylenes prepared in this study do not exhibit columnar mesophases, variable concentration H-1 NMR studies provide evidence for aggregation in solution.