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Chemical Bonding

Chemists create smaller all-carbon rings

Cyclo[10]carbon’s and cyclo[14]carbon’s bonds differ from those of larger all-carbon rings

by Bethany Halford
December 3, 2023 | A version of this story appeared in Volume 101, Issue 40


The structures of cyclo[10]carbon and cyclo[14]carbon along with AFM images that show rings with bonds of similar character.
Credit: Adapted fromNature
AFM shows that C10 has a cumulenic structure, and C14 is in between cumulenic and polyynic, as indicated by double bonds of different colors.

Two new carbon allotropes have been zapped into being and imaged using atomic force microscopy (AFM). Researchers at Tongji University led by Wei Xu used on-surface synthesis to make rings composed of 10 and 14 carbon atoms, known as cyclo[10]carbon (C10) and cyclo[14]carbon (C14) . Although C10 and C14 have been studied in the gas phase, this is the first time that chemists have managed to make and characterize them on a surface, an accomplishment that gives deeper insight into their bonding.

To make C10 and C14, Xu’s team started with fully chlorinated naphthalene (C10 Cl8) and anthracene (C14 Cl10) and used an AFM tip to gradually pluck off chlorines. Removing the chlorines prompted the precursor molecules to undergo ring-opening reactions, which ultimately produced the 10- and 14-carbon rings (Nature 2023, DOI: 10.1038/s41586-023-06741-x).

The synthesis differs from that of cyclo[16]carbon( C16) and cyclo[18]carbon( C18) , which used more complex precursors. The University of Oxford’s Harry L. Anderson, who co-led the syntheses of those larger rings, says in an email that starting with readily available polycyclic aromatic chlorocarbons “will open up the field by making cyclocarbons easier to synthesize.”

AFM imaging reveals that C10’s and C14’s bonding characters are distinct from their larger all-carbon siblings, C16 and C18. Bonds in the larger rings are polyynic, meaning that they alternate between single and triple bonds. C10’s bonds are cumulenic—essentially consecutive double bonds. C14 also has only double bonds, but those bonds are not all the same, which indicates that the molecule is somewhere in between cumulenic and polyynic.

IBM Research-Zurich’s Leo Gross, who collaborated with Anderson on the syntheses of C16 and C18, says it’s great to see that C10 has the cumulenic structure predicted by theory and that C14 is a transition structure between cumulenic and polyynic. “For us experimentalists it is nice that we see cyclocarbons in all these different forms,” he says in an email.


This story was updated on Jan. 2, 2024, to correct the formula for chlorinated naphthalene. It is C10Cl8, not C10Cl8.



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