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Issue 38, 2011
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A molecular bowl sumanene

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Nonplanar polyaromatic carbon molecules including fullerenes and carbon nanotubes have been attracting great interest due to their potential as materials, catalysts, etc. In this context, bowl-shaped polyaromatic hydrocarbons (π bowls) are considered to be key materials in the science of nonplanar π-conjugated carbon systems. Among π bowls, we focused on a molecular bowl “sumanene (C21H12)” featuring a C3v symmetric structural motif present in fullerenes or carbon nanotube molecules. In this article, we present the research on sumanenes to date, including their synthesis, structural characterization, derivatization, complexation, and their potential uses as electrical materials. The characteristic structural feature of a sumanene depends on three sp3 hybridized carbon atoms at the benzylic positions. Facile functionalization via selective formation of benzylic anions gives stereoselective substituted compounds, the π-extended derivatives, and the deeper π bowls. Furthermore, the dynamically flexible aspect based on bowl-to-bowl inversion is also described. The crystal with a columnar bowl-in-bowl stacking exhibits a high electron transport ability with anisotropy. Complexation with a cyclopentadienyl iron cation results in the first selective formation of the concave-bound complex as a π-bowl complex.

Graphical abstract: A molecular bowl sumanene

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The article was received on 30 Apr 2011, accepted on 13 Jun 2011 and first published on 08 Jul 2011

Article type: Feature Article
DOI: 10.1039/C1CC12532J
Citation: Chem. Commun., 2011,47, 10524-10535
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    A molecular bowl sumanene

    T. Amaya and T. Hirao, Chem. Commun., 2011, 47, 10524
    DOI: 10.1039/C1CC12532J

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