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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机译：弯曲的π共轭分子由于其弯曲的π表面而产生的独特性质引起了人们的极大兴趣。然而，这种扭曲的分子的合成需要苛刻的条件，这阻碍了容易接近含杂原子的弯曲π系统。在这里，我们报告了一个以氮为中心的π-延伸的氮杂蒽环的合成方法。 9-氨基菲的氧化提供了四苯并咔唑，四苯并咔唑通过钯催化的分子内偶联转化为氮杂巴克杯。杜鹃桶的供电子性质和弯曲的π表面使其在溶液和固态下均与C 60 紧密结合。氮杂巴克/ C 60 组件观察到高电荷迁移率。该化合物作为富勒烯主体，各向异性π供体和含氮纳米碳材料的前体，可能在弯曲π系统领域中受到关注。
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