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Supramolecular assemblies of a nitrogen-embedded buckybowl dimer with C60

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Abstract

A directly connected azabuckybowl dimer was synthesized via a palladium-catalysed C–H/C–Br coupling. The electron-donating nature of the pyrrolic nitrogen atoms of the azabuckybowl enabled a strong complexation with pristine C60. In the presence of two equivalents of C60, the azabuckybowl dimer formed crystals with a 1 : 2 stoichiometry. Conversely, in diluted solution, complexes with a 1 : 1 stoichiometry of the dimer and C60 were detected predominantly, and these precipitated upon increasing the concentration of C60. Scanning electron microscopy images of the precipitate showed fibre-like aggregates, indicating the formation of supramolecular assemblies with 1D chain structures. A variable-temperature 1H NMR analysis revealed that the precipitate consists of the dimer and C60 in a 1 : 1 ratio.

Graphical abstract: Supramolecular assemblies of a nitrogen-embedded buckybowl dimer with C60

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Publication details

The article was received on 15 Oct 2017, accepted on 20 Nov 2017 and first published on 21 Nov 2017


Article type: Edge Article
DOI: 10.1039/C7SC04453D
Citation: Chem. Sci., 2018, Advance Article
  • Open access: Creative Commons BY-NC license
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    Supramolecular assemblies of a nitrogen-embedded buckybowl dimer with C60

    H. Yokoi, S. Hiroto, D. Sakamaki, S. Seki and H. Shinokubo, Chem. Sci., 2018, Advance Article , DOI: 10.1039/C7SC04453D

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