Cagatay Dengiz

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.

Nitrogen Analogues of Polycyclic Aromatic Hydrocarbons

Significance: Nitrogen-containing polyaromatic hydrocarbons are well-known for their stability and spectacular optoelectronic properties. The authors report a facile and efficient approach to access structurally demanding polycyclic azaarenes: diazabenzopyrene and diazaperylene. In general, synthetic approaches to azaarenes are limited to aromatic amines as starting materials. The visible-light photocyclization of vinyl azide derivatives is an important alternative to overcome the above-mentioned limitation. Comment: The authors demonstrate the efficient synthesis of nitrogen-containing polyaromatic hydrocarbons starting from vinyl azide functionalized anthracene substrates. The photocatalyst-free, visible-light photocyclization of vinyl azide derivatives of anthracenes suggests possible applications for the syntheses of previously inaccessible nitrogen-containing polycyclic aromatics. O