Electrochemical deposition of N-heterocyclic carbene monolayers on metal surfaces

Einav Amit, Linoy Dery, Shahar Dery, Suhong Kim, Anirban Roy, Qichi Hu, Vitaly Gutkin, Helen Eisenberg, Tamar Stein, Daniel Mandler, F. Dean Toste and Elad Gross ()
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Einav Amit: The Hebrew University
Linoy Dery: The Hebrew University
Shahar Dery: The Hebrew University
Suhong Kim: University of California
Anirban Roy: Bruker Nano Surfaces Division
Qichi Hu: Bruker Nano Surfaces Division
Vitaly Gutkin: The Hebrew University
Helen Eisenberg: The Hebrew University
Tamar Stein: The Hebrew University
Daniel Mandler: The Hebrew University
F. Dean Toste: University of California
Elad Gross: The Hebrew University

Nature Communications, 2020, vol. 11, issue 1, 1-10

Abstract: Abstract N-heterocyclic carbenes (NHCs) have been widely utilized for the formation of self-assembled monolayers (SAMs) on various surfaces. The main methodologies for preparation of NHCs-based SAMs either requires inert atmosphere and strong base for deprotonation of imidazolium precursors or the use of specifically-synthesized precursors such as NHC(H)[HCO3] salts or NHC–CO2 adducts. Herein, we demonstrate an electrochemical approach for surface-anchoring of NHCs which overcomes the need for dry environment, addition of exogenous strong base or restricting synthetic steps. In the electrochemical deposition, water reduction reaction is used to generate high concentration of hydroxide ions in proximity to a metal electrode. Imidazolium cations were deprotonated by hydroxide ions, leading to carbenes formation that self-assembled on the electrode’s surface. SAMs of NO2-functionalized NHCs and dimethyl-benzimidazole were electrochemically deposited on Au films. SAMs of NHCs were also electrochemically deposited on Pt, Pd and Ag films, demonstrating the wide metal scope of this deposition technique.

Date: 2020
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DOI: 10.1038/s41467-020-19500-7

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