Nitrogen-embedded buckybowl and its assembly with C60

Hiroki Yokoi, Yuya Hiraoka, Satoru Hiroto (), Daisuke Sakamaki, Shu Seki and Hiroshi Shinokubo ()
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Hiroki Yokoi: Graduate School of Engineering, Nagoya University
Yuya Hiraoka: Graduate School of Engineering, Nagoya University
Satoru Hiroto: Graduate School of Engineering, Nagoya University
Daisuke Sakamaki: Graduate School of Engineering, Kyoto University
Shu Seki: Graduate School of Engineering, Kyoto University
Hiroshi Shinokubo: Graduate School of Engineering, Nagoya University

Nature Communications, 2015, vol. 6, issue 1, 1-9

Abstract: 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.

Date: 2015
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DOI: 10.1038/ncomms9215

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