Journal Article Nitrogen-embedded buckybowl and its assembly with C[60]

Yokoi, Hiroki  ,  Hiraoka, Yuya  ,  Hiroto, Satoru  ,  Sakamaki, Daisuke  ,  Seki, Shu  ,  Shinokubo, 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[60] in solution and solid states. High charge mobility is observed for the azabuckybowl/C[60] 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.

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