Naphthazarin-Polycyclic Conjugated Hydrocarbons and Iptycenes

The synthesis of a set of naphthazarin-containing polycyclic conjugated hydrocarbons is described herein. Sequential Diels–Alder reactions on a tautomerized naphthazarin core were employed to access the final conjugated systems. Complete conjugation across the backbone can be achieved through complexation with BF2, as observed by 1H NMR analysis and UV/vis spectroscopy. Precise synthetic control over the degree of oxidation of naphthazarin quinone Diels–Alder adduct 10 is additionally demonstrated and enables us to direct its subsequent reactivity. Finally, this work serves to demonstrate the potential for naphthazarin as a building block in the synthesis of novel organic electronic materials.