Synthesis of Cyclo[18]carbon via Debromination of C18Br6

Cyclo­[18]carbon (C18, a molecular carbon allotrope) can be synthesized by dehalogenation of a bromocyclocarbon precursor, C18Br6, in 64% yield, by atomic manipulation on a sodium chloride bilayer on Cu(111) at 5 K, and imaged by high-resolution atomic force microscopy. This method of generating C18...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2020-07, Vol.142 (30), p.12921-12924
Main Authors: Scriven, Lorel M, Kaiser, Katharina, Schulz, Fabian, Sterling, Alistair J, Woltering, Steffen L, Gawel, Przemyslaw, Christensen, Kirsten E, Anderson, Harry L, Gross, Leo
Format: Article
Language:English
Subjects:
Communication
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Summary:Cyclo­[18]carbon (C18, a molecular carbon allotrope) can be synthesized by dehalogenation of a bromocyclocarbon precursor, C18Br6, in 64% yield, by atomic manipulation on a sodium chloride bilayer on Cu(111) at 5 K, and imaged by high-resolution atomic force microscopy. This method of generating C18 gives a higher yield than that reported previously from the cyclocarbon oxide C24O6. The experimental images of C18 were compared with simulated images for four theoretical model geometries, including possible bond-angle alternation: D 18h cumulene, D 9h polyyne, D 9h cumulene, and C 9h polyyne. Cumulenic structures, with (D 9h ) and without (D 18h ) bond-angle alternation, can be excluded. Polyynic structures, with (C 9h ) and without (D 9h ) bond-angle alternation, both show a good agreement with the experiment and are challenging to differentiate.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.0c05033