Aromatic Azide Transformation on the Ag(111) Surface Studied by Scanning Probe Microscopy

Jack Hellerstedt, Ales Cahlik, Oleksander Stetsovych, Martin Svec, Tomoko K Shimizu, Pingo Mutombo, Jiri Klivar, Irena G Stara, Pavel Jelinek, Ivo Stary

Research output: Contribution to journalArticleResearchpeer-review

Abstract

Chemical transformation of 9‐azidophenanthrene on the Ag(111) surface was studied by nc‐AFM in UHV. High‐resolution imaging supported by first‐principle calculations revealed the structure of the final products that originated from a common and elusive 9‐phenanthryl nitrenoid intermediate chemisorbed on the Ag(111) surface. A formal nitrene insertion into the C−H bond along with its dimerisation and hydrogenation were identified as main reaction channels. Thus, the ability of aryl azides to form covalent σ‐ and π‐bonds between their transformation products on a solid surface was demonstrated at a single‐molecule level.
Original languageEnglish
Number of pages7
Journal Angewandte Chemie - International Edition
DOIs
Publication statusAccepted/In press - 2019

Keywords

  • azides
  • density functional calculations
  • on-surface chemistry
  • scanning probe microscopy
  • silver surface

Cite this

Hellerstedt, Jack ; Cahlik, Ales ; Stetsovych, Oleksander ; Svec, Martin ; Shimizu, Tomoko K ; Mutombo, Pingo ; Klivar, Jiri ; Stara, Irena G ; Jelinek, Pavel ; Stary, Ivo. / Aromatic Azide Transformation on the Ag(111) Surface Studied by Scanning Probe Microscopy. In: Angewandte Chemie - International Edition. 2019.
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abstract = "Chemical transformation of 9‐azidophenanthrene on the Ag(111) surface was studied by nc‐AFM in UHV. High‐resolution imaging supported by first‐principle calculations revealed the structure of the final products that originated from a common and elusive 9‐phenanthryl nitrenoid intermediate chemisorbed on the Ag(111) surface. A formal nitrene insertion into the C−H bond along with its dimerisation and hydrogenation were identified as main reaction channels. Thus, the ability of aryl azides to form covalent σ‐ and π‐bonds between their transformation products on a solid surface was demonstrated at a single‐molecule level.",
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Aromatic Azide Transformation on the Ag(111) Surface Studied by Scanning Probe Microscopy. / Hellerstedt, Jack; Cahlik, Ales; Stetsovych, Oleksander; Svec, Martin; Shimizu, Tomoko K; Mutombo, Pingo; Klivar, Jiri; Stara, Irena G; Jelinek, Pavel; Stary, Ivo.

In: Angewandte Chemie - International Edition, 2019.

Research output: Contribution to journalArticleResearchpeer-review

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AU - Hellerstedt, Jack

AU - Cahlik, Ales

AU - Stetsovych, Oleksander

AU - Svec, Martin

AU - Shimizu, Tomoko K

AU - Mutombo, Pingo

AU - Klivar, Jiri

AU - Stara, Irena G

AU - Jelinek, Pavel

AU - Stary, Ivo

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AB - Chemical transformation of 9‐azidophenanthrene on the Ag(111) surface was studied by nc‐AFM in UHV. High‐resolution imaging supported by first‐principle calculations revealed the structure of the final products that originated from a common and elusive 9‐phenanthryl nitrenoid intermediate chemisorbed on the Ag(111) surface. A formal nitrene insertion into the C−H bond along with its dimerisation and hydrogenation were identified as main reaction channels. Thus, the ability of aryl azides to form covalent σ‐ and π‐bonds between their transformation products on a solid surface was demonstrated at a single‐molecule level.

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KW - density functional calculations

KW - on-surface chemistry

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