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Synthesis of a carbon nanobelt

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Science  14 Apr 2017:
Vol. 356, Issue 6334, pp. 172-175
DOI: 10.1126/science.aam8158

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Stitching a belt out of carbon rings

If you had a molecular scalpel, you could slice a carbon nanotube twice against the long axis to excise a loop of fused phenyl rings. Of course, knives don't come that small. Instead, Povie et al. succeeded in stitching together such a nanometer-scale belt in bottom-up fashion from molecular components, using consecutive Wittig reactions (see the Perspective by Siegel). The belt of 12 edge-sharing rings could ultimately be a first step toward more precisely controlled bottom-up syntheses of extended nanotubes.

Science, this issue p. 172; see also p. 135

Abstract

The synthesis of a carbon nanobelt, comprising a closed loop of fully fused edge-sharing benzene rings, has been an elusive goal in organic chemistry for more than 60 years. Here we report the synthesis of one such compound through iterative Wittig reactions followed by a nickel-mediated aryl-aryl coupling reaction. The cylindrical shape of its belt structure was confirmed by x-ray crystallography, and its fundamental optoelectronic properties were elucidated by ultraviolet-visible absorption, fluorescence, and Raman spectroscopic studies, as well as theoretical calculations. This molecule could potentially serve as a seed for the preparation of structurally well-defined carbon nanotubes.

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