Nitrogen-embedded buckybowl and its assembly with C-60

作者：Yokoi Hiroki; Hiraoka Yuya; Hiroto Satoru; Sakamaki Daisuke; Seki Shu; Shinokubo Hiroshi

来源：Nature Communications, 2015, 6(1): 8215.

DOI：10.1038/ncomms9215

Curved pi-conjugated molecules have attracted considerable interest because of the unique properties originating from their curved pi surface. However, the synthesis of such distorted molecules requires harsh conditions, which hamper easy access to heteroatom-containing curved pi systems. Here we report the synthesis of a pi-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 pi 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 pi systems as fullerene hosts, anisotropic p donors and precursors to nitrogen-containing nanocarbon materials.

• 出版日期2015-9