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Synfacts 2017; 13(07): 0697
DOI: 10.1055/s-0036-1590570
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Nanobelt Mission Accomplished: A Loop of 12 Fused Edge-Sharing Benzenes

Contributor(s):
Timothy M. Swager
,
Lukas Zeininger
Povie G. Segawa Y. * Nishihara T. Miyauchi Y. Itami K. * Japan Science and Technology Agency, Exploratory Research for Advanced Technology, Nagoya, Nagoya University, and Kyoto University, Japan
Synthesis of a Carbon Nanobelt.

Science 2017;
356: 172-175
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Publication History

Publication Date:
19 June 2017 (online)

 
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Key words

aryl–aryl coupling - Wittig reaction - carbon nanobelt

Significance

The synthesis of a fully fused carbon nanobelt (7) — a belt segment of a (6,6)carbon nanotube — has been a long-lasting goal in materials science. Segawa, Itami, and co-workers have now reported on the successful bottom-up synthesis of such a carbon nanobelt, a closed loop of 12 fully fused edge-sharing benzene rings. The synthesis starts with several consecutive ­Wittig reactions. In the final step, a Ni(cod)2-mediated aryl–aryl coupling reaction prompts the formation of the new fully fused arene system.


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Comment

The authors studied in detail the optoelectronic and structural properties of this ‘shortest armchair carbon nanotube’. Besides verifying the rigid cylindrical shape of this carbon nanobelt through X-ray crystallography, its photophysical characterization combined with theoretical calculations confirmed the structural rigidity of this fully conjugated arene system. The synthesis of this belt of 12 edge-sharing benzene rings may pave the way towards a precisely controlled single-­chirality bottom-up synthesis of (6,6)carbon nanotubes.


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