Self-assembly of N-heterocyclic carbenes on Au(111)

Alex Inayeh, Ryan R. K. Groome, Ishwar Singh, Alex J. Veinot, Felipe Crasto Lima, Roberto H. Miwa, Cathleen M. Crudden () and Alastair B. McLean ()
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Alex Inayeh: Queen’s University
Ryan R. K. Groome: Queen’s University
Ishwar Singh: Queen’s University
Alex J. Veinot: Queen’s University
Felipe Crasto Lima: Instituto de Física, Universidade Federal de Uberlândia
Roberto H. Miwa: Instituto de Física, Universidade Federal de Uberlândia
Cathleen M. Crudden: Queen’s University
Alastair B. McLean: Queen’s University

Nature Communications, 2021, vol. 12, issue 1, 1-9

Abstract: Abstract Although the self-assembly of organic ligands on gold has been dominated by sulfur-based ligands for decades, a new ligand class, N-heterocyclic carbenes (NHCs), has appeared as an interesting alternative. However, fundamental questions surrounding self-assembly of this new ligand remain unanswered. Herein, we describe the effect of NHC structure, surface coverage, and substrate temperature on mobility, thermal stability, NHC surface geometry, and self-assembly. Analysis of NHC adsorption and self-assembly by scanning tunneling microscopy and density functional theory have revealed the importance of NHC-surface interactions and attractive NHC-NHC interactions on NHC monolayer structures. A remarkable way these interactions manifest is the need for a threshold NHC surface coverage to produce upright, adatom-mediated adsorption motifs with low surface diffusion. NHC wingtip structure is also critical, with primary substituents leading to the formation of flat-lying NHC2Au complexes, which have high mobility when isolated, but self-assemble into stable ordered lattices at higher surface concentrations. These and other studies of NHC surface chemistry will be crucial for the success of these next-generation monolayers.

Date: 2021
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DOI: 10.1038/s41467-021-23940-0

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