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

doi:10.1002/chem.202002308

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

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Journal	Chemistry - A European Journal
Volume	Early View
Early online date	7 Aug 2020
DOIs	https://doi.org/10.1002/chem.202002308
Publication status	E-pub ahead of print - 7 Aug 2020

Keywords

N-Heterocyclic carbene
Copper oxide
Reduction
Self assembled monolayer

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10.1002/chem.202002308

Veinot_2020_CEJ_onepot_AAM
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
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@article{d3c26e6c91ba483fafa14e0eab755443,

title = "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.",

keywords = "N-Heterocyclic carbene, Copper oxide, Reduction, Self assembled monolayer",

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

note = "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.",

year = "2020",

month = aug,

day = "7",

doi = "10.1002/chem.202002308",

language = "English",

volume = "Early View",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "John Wiley & Sons, Ltd",

}

TY - JOUR

T1 - N-heterocyclic carbenes reduce and functionalize copper oxide surfaces in one pot

AU - Veinot, Alex

AU - Al-Rashed, Abrar

AU - Padmos, J. Daniel

AU - Singh, Ishwar

AU - Lee, Dianne S.

AU - Narouz, Mina R.

AU - Lummis, Paul A.

AU - Baddeley, Christopher J.

AU - Crudden, Cathleen Marie

AU - Horton, J. Hugh

N1 - 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.

PY - 2020/8/7

Y1 - 2020/8/7

N2 - 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.

AB - 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.

KW - N-Heterocyclic carbene

KW - Copper oxide

KW - Reduction

KW - Self assembled monolayer

U2 - 10.1002/chem.202002308

DO - 10.1002/chem.202002308

M3 - Article

SN - 0947-6539

VL - Early View

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

ER -

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

Abstract

Keywords

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