On-surface synthesis of a doubly anti-aromatic carbon allotrope

Yueze Gao, Florian Albrecht, Igor Rončević, Isaac Ettedgui, Paramveer Kumar, Lorel M. Scriven, Kirsten E. Christensen, Shantanu Mishra, Luca Righetti, Max Rossmannek, Ivano Tavernelli, Harry L. Anderson () and Leo Gross ()
Additional contact information
Yueze Gao: Oxford University, Chemistry Research Laboratory
Florian Albrecht: IBM Research Europe – Zürich
Igor Rončević: Oxford University, Chemistry Research Laboratory
Isaac Ettedgui: Oxford University, Chemistry Research Laboratory
Paramveer Kumar: Oxford University, Chemistry Research Laboratory
Lorel M. Scriven: Oxford University, Chemistry Research Laboratory
Kirsten E. Christensen: Oxford University, Chemistry Research Laboratory
Shantanu Mishra: IBM Research Europe – Zürich
Luca Righetti: IBM Quantum, IBM Research – Zürich
Max Rossmannek: IBM Quantum, IBM Research – Zürich
Ivano Tavernelli: IBM Quantum, IBM Research – Zürich
Harry L. Anderson: Oxford University, Chemistry Research Laboratory
Leo Gross: IBM Research Europe – Zürich

Nature, 2023, vol. 623, issue 7989, 977-981

Abstract: Abstract Synthetic carbon allotropes such as graphene1, carbon nanotubes2 and fullerenes3 have revolutionized materials science and led to new technologies. Many hypothetical carbon allotropes have been discussed4, but few have been studied experimentally. Recently, unconventional synthetic strategies such as dynamic covalent chemistry5 and on-surface synthesis6 have been used to create new forms of carbon, including γ-graphyne7, fullerene polymers8, biphenylene networks9 and cyclocarbons10,11. Cyclo[N]carbons are molecular rings consisting of N carbon atoms12,13; the three that have been reported to date (N = 10, 14 and 18)10,11 are doubly aromatic, which prompts the question: is it possible to prepare doubly anti-aromatic versions? Here we report the synthesis and characterization of an anti-aromatic carbon allotrope, cyclo[16]carbon, by using tip-induced on-surface chemistry6. In addition to structural information from atomic force microscopy, we probed its electronic structure by recording orbital density maps14 with scanning tunnelling microscopy. The observation of bond-length alternation in cyclo[16]carbon confirms its double anti-aromaticity, in concordance with theory. The simple structure of C16 renders it an interesting model system for studying the limits of aromaticity, and its high reactivity makes it a promising precursor to novel carbon allotropes15.

Date: 2023
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DOI: 10.1038/s41586-023-06566-8

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