Highly ordered N-heterocyclic carbene monolayers on Cu(111)

Eloise Angove, Federico Grillo, Herbert A. Fruchtl, Alex, J Veinot, Ishwar Singh, J Hugh Horton, Cathleen M Crudden, Christopher J. Baddeley*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

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Abstract

The benzannulated N-heterocyclic carbene, 1,3-dibenzylbenzimidazolylidene (NHCDBZ) forms large, highly ordered domains when adsorbed on Cu(111) under ultrahigh vacuum conditions. A combination of scanning tunnelling microscopy (STM), high resolution electron energy loss spectroscopy (HREELS) and density functional theory (DFT) calculations reveals that the overlayer consists of vertical benzannulated NHC moieties coordinating to Cu adatoms. Long range order results from the placement of the two benzyl substituents on opposite sides of the benzimidazole moiety, with their aromatic rings approximately parallel to the surface. The organization of three surface-bound benzyl substituents from three different NHCs into a triangular array controls the formation of a highly ordered Kagome-like surface lattice. By comparison with earlier studies of NHCs on Cu(111), we show that the binding geometry and self-assembly of NHCDBZ are influenced by intermolecular and adsorbate-substrate interactions and facilitated by the flexibility of the methylene linkage between the N-heterocycle and the aromatic wingtip substituents.
Original languageEnglish
Pages (from-to)2051-2056
JournalThe Journal of Physical Chemistry Letters
Volume13
Issue number8
Early online date24 Feb 2022
DOIs
Publication statusE-pub ahead of print - 24 Feb 2022

Keywords

  • N-heterocyclic carbene
  • Scanning tunneling microscopy
  • High resolution electron energy loss spectroscopy
  • Cu

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