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

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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.
Original languageEnglish
Pages (from-to)2266-2271
Number of pages6
JournalAngewandte Chemie - International Edition
Volume58
Issue number8
DOIs
Publication statusPublished - 2019

Keywords

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

Cite this

Hellerstedt, J., Cahlik, A., Stetsovych, O., Svec, M., Shimizu, T. K., Mutombo, P., Klivar, J., Stara, I. G., Jelinek, P., & Stary, I. (2019). Aromatic Azide Transformation on the Ag(111) Surface Studied by Scanning Probe Microscopy. Angewandte Chemie - International Edition, 58(8), 2266-2271. https://doi.org/10.1002/anie.201812334