Polycyclic aromatic triptycenes: oxygen substitution cyclization strategies.

The cyclization and planarization of polycyclic aromatic hydrocarbons with concomitant oxygen substitution was achieved through acid catalyzed transetherification and oxygen-radical reactions. The triptycene scaffold enforces proximity of the alcohol and arene reacting partners and confers significant rigidity to the resulting π-system, expanding the tool set of iptycenes for materials applications.