Synthesis and Photophysical Properties of Soluble N‐Doped Rubicenes via Ruthenium‐Catalyzed Transfer Hydrogenative Benzannulation

Ruthenium‐catalyzed butadiene‐mediated benzannulation enabled the first synthesis of 3,10‐(di‐tert‐butyl)rubicene and its N‐doped derivatives as well as preliminary studies on their photophysical properties. Unlike the parent rubicene and 3,10‐(di‐tert‐butyl)rubicene, which adopt classical herringbone‐type packing motifs in the solid state, the N‐doped congener 7 b displayed columnar packing with an alternating co‐facial arrangement of aromatic and heteroaromatic substructures. Ruby Red: Ruthenium‐catalyzed butadiene‐mediated benzannulation enables the first synthesis of 3,10‐(di‐tert‐butyl)rubicene and its N‐doped derivatives as well as preliminary studies on their photophysical properties. Unlike the parent rubicene and 3,10‐(di‐tert‐butyl)rubicene, which adopt classical herringbone‐type packing motifs in the solid state, the N‐doped congener 7 b displays columnar packing with an alternating co‐facial arrangement of aromatic and heteroaromatic substructures.