ArticleNature chemistry2015
On-surface generation and imaging of arynes by atomic force microscopy.
Article in Nature chemistry, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 60 papers.
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Who cites it
60 citing papers in PubMed.
- Tuning aromaticity of cyclocarbons by heteroatom doping: CNational science review · 2026Article
- The versatile world of cumulene chemistry.Chemical science · 2026Review
- On-surface synthesis of cyclo[20]carbon and cyclo[30]carbon from cyclo[10]carbon.Nature communications · 2025Article
- Skeletal Editing by Tip-Induced Chemistry.Journal of the American Chemical Society · 2025Article
- The cumulenic linear CNature communications · 2025Article
- Probing weak chemical interactions of metal surface atoms with CO-terminated AFM tips identifies molecular adsorption sites.Nature communications · 2025Article
- A Review of On-Surface Synthesis and Characterization of Macrocycles.Nanomaterials (Basel, Switzerland) · 2025Review
- Probing Molecular Properties at Atomic Length Scale Using Charge-State Control.Chemical reviews · 2025Review
- On-Surface Synthesis and Cryogenic Exfoliation of Sterically Frustrated Atropisomers.ACS nano · 2025Article
- Article
- Switchable chemoselective aryne reactions between nucleophiles and pericyclic reaction partners using either 3-methoxybenzyne or 3-silylbenzyne.Nature communications · 2024Article
- Universal inter-molecular radical transfer reactions on metal surfaces.Nature communications · 2024Article
- Local probe-induced structural isomerization in a one-dimensional molecular array.Nature communications · 2023Article
- Article
- Observation of the Magnetic Ground State of the Two Smallest Triangular Nanographenes.JACS Au · 2023Article
- Tuning the Diradical Character of Pentacene Derivatives via Non-Benzenoid Coupling Motifs.Journal of the American Chemical Society · 2023Article
- Advances in the synthesis of nitrogen-containing heterocyclic compounds byRSC advances · 2023Review
- In Situ Observation of C-C Coupling and Step Poisoning During the Growth of Hydrocarbon Chains on Ni(111).Angewandte Chemie (International ed. in English) · 2023Article
- Small molecule binding to surface-supported single-site transition-metal reaction centres.Nature communications · 2022Article
- Porphyryne.ACS omega · 2022Article
Corrections and comments
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Authors and funding
9 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Reactive intermediates are involved in many chemical transformations. However, their characterization is a great challenge because of their short lifetimes and high reactivities. Arynes, formally derived from arenes by the removal of two hydrogen atoms from adjacent carbon atoms, are prominent reactive intermediates that have been hypothesized for more than a century. Their rich chemistry enables a widespread use in synthetic chemistry, as they are advantageous building blocks for the construction of polycyclic compounds that contain aromatic rings. Here, we demonstrate the generation and characterization of individual polycyclic aryne molecules on an ultrathin insulating film by means of low-temperature scanning tunnelling microscopy and atomic force microscopy. Bond-order analysis suggests that a cumulene resonance structure is the dominant one, and the aryne reactivity is preserved at cryogenic temperatures. Our results provide important insights into the chemistry of these elusive intermediates and their potential application in the field of on-surface synthesis.
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26201737What OpenQuestion holds
Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.