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.
- density functional calculations
- on-surface chemistry
- scanning probe microscopy
- silver surface
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