N-heterocyclic carbenes reduce and functionalize copper oxide surfaces in one pot
Abstract
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.
Citation
Veinot , A , Al-Rashed , A , Padmos , J D , Singh , I , Lee , D S , Narouz , M R , Lummis , P A , Baddeley , C J , Crudden , C M & Horton , J H 2020 , ' N-heterocyclic carbenes reduce and functionalize copper oxide surfaces in one pot ' , Chemistry - A European Journal , vol. Early View . https://doi.org/10.1002/chem.202002308
Publication
Chemistry - A European Journal
Status
Peer reviewed
ISSN
0947-6539Type
Journal article
Rights
Copyright © 2020 Wiley‐VCH GmbH. This work has been made available online in accordance with publisher policies or with permission. Permission for further reuse of this content should be sought from the publisher or the rights holder. This is the author created accepted manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1002/chem.202002308
Description
The Natural Sciences and Engineering Research Council of Canada (NSERC) and the Canada Foundation for Innovation (CFI) are thanked for financial support of this work in terms of operating and equipment grants to CMC and JHH. AJV and MRN thank the Ontario government for OGS fellowships. AJV thanks NSERC for a Vanier Scholarship and also the Walter C. Sumner foundation for additional scholarship support.Collections
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