Nitrogen-embedded buckybowl and its assembly with C60

Nature Communications
Hiroki YokoiHiroshi Shinokubo

Abstract

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 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.

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Citations

Mar 19, 2016·Journal of the American Chemical Society·Yoshifumi HashikawaYasujiro Murata
Jun 30, 2016·Journal of the American Chemical Society·Junzhi LiuKlaus Müllen
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Methods Mentioned

BETA
X-ray
nuclear magnetic resonance
two-dimensional exchange spectroscopy
electron spin resonance
ESR

Software Mentioned

Gaussian
ORTEP
DFIX

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