Nitrogen-embedded buckybowl and its assembly with C60

• DOI: 10.1038/ncomms9215
• Publication Date: 2015-09-04T10:09:43Z
• Authors: Hiroki Yokoi; Yuya Hiraoka; Satoru Hiroto; Daisuke Sakamaki; Shu Seki; Hiroshi Shinokubo
• Keywords: Chemical sciences; Organic chemistry; 01 natural sciences; Article; 0104 chemical sciences

AbstractCurved 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 C60 in solution and solid states. High charge mobility is observed for the azabuckybowl/C60 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.