||Nitrogen-embedded buckybowl and its assembly with C
Yokoi, Hiroki ,
Hiraoka, Yuya ,
Hiroto, Satoru ,
Sakamaki, Daisuke ,
Seki, ShuShinokubo, Hiroshi
62015-09-04 , Nature Publishing Group
Curved π-conjugated molecules have attracted considerable interest because of the unique properties originating from their curved π surface. However, the synthesis of such distorted molecules requires harsh conditions, which hamper easy access to heteroatom-containing curved π systems. Here we report the synthesis of a π-extended azacorannulene with nitrogen in its centre. The oxidation of 9-aminophenanthrene provides tetrabenzocarbazole, which is converted to the azabuckybowl through palladium-catalysed intramolecular coupling. The electron-donating nature and curved π surface of the azabuckybowl enable its tight association with C in solution and solid states. High charge mobility is observed for the azabuckybowl/C assembly. This compound may be of interest in the fields of curved π systems as fullerene hosts, anisotropic π donors and precursors to nitrogen-containing nanocarbon materials.