N-heterocyclic carbenes reduce and functionalize copper oxide surfaces in one pot

Alex Veinot, Abrar Al-Rashed, J. Daniel Padmos, Ishwar Singh, Dianne S. Lee, Mina R. Narouz, Paul A. Lummis, Christopher J. Baddeley, Cathleen Marie Crudden, J. Hugh Horton

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Benzimidazolium hydrogen carbonate salts have been shown to act as N-heterocyclic carbene precursors which can remove oxide from copper oxide surfaces and functionalize the resulting metallic surfaces in a single step. Both the surfaces and the etching products are fully characterized by spectroscopic methods. Analysis of surfaces before and after NHC treatment by X-ray photoelectron spectroscopy demonstrates the complete removal of copper(II) oxide. Using 13C-labelling, we determine that the products of this transformation include a cyclic urea, a ring-opened formamide and a bis-carbene copper(I) complex. These results illustrate the potential of NHCs to functionalize a much broader class of metals, including those prone to oxide treatment, greatly facilitating the preparation of NHC-based films on metals other than gold.
Original languageEnglish
JournalChemistry - A European Journal
VolumeEarly View
Early online date7 Aug 2020
Publication statusE-pub ahead of print - 7 Aug 2020


  • N-Heterocyclic carbene
  • Copper oxide
  • Reduction
  • Self assembled monolayer


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