Issue 4, 2018

Supramolecular assemblies of a nitrogen-embedded buckybowl dimer with C60

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

Supplementary files

Article information

Article type
Edge Article
Submitted
15 Oct 2017
Accepted
20 Nov 2017
First published
21 Nov 2017
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2018,9, 819-824

Supramolecular assemblies of a nitrogen-embedded buckybowl dimer with C60

H. Yokoi, S. Hiroto, D. Sakamaki, S. Seki and H. Shinokubo, Chem. Sci., 2018, 9, 819 DOI: 10.1039/C7SC04453D

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