N-heterocyclic carbene self-assembled monolayers on copper and gold: dramatic effect of wingtip groups on binding, orientation and assembly

Christian Rodriguez Larrea, Christopher John Baddeley*, Mina R. Narouz, Nicholas J. Mosey, J. Hugh Horton, Cathleen M. Crudden

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

44 Citations (Scopus)
4 Downloads (Pure)

Abstract

Self‐assembled monolayers of N‐heterocyclic carbenes (NHCs) on copper are reported. The monolayer structure is highly dependent on the N,N‐substituents on the NHC. On both Cu(111) and Au(111), bulky isopropyl substituents force the NHC to bind perpendicular to the metal surface while methyl‐ or ethyl‐substituted NHCs lie flat. Temperature‐programmed desorption studies show that the NHC binds to Cu(111) with a desorption energy of Edes=152±10 kJ mol−1. NHCs that bind upright desorb cleanly, while flat‐lying NHCs decompose leaving adsorbed organic residues. Scanning tunneling microscopy of methylated NHCs reveals arrays of covalently linked dimers which transform into adsorbed (NHC)2Cu species by extraction of a copper atom from the surface after annealing.
Original languageEnglish
Pages (from-to)3536–3539
JournalChemPhysChem
Volume18
Issue number24
Early online date2 Nov 2017
DOIs
Publication statusPublished - 21 Dec 2017

Keywords

  • N-heterocyclic carbenes
  • Copper
  • Self assembled monolayers
  • Orientation
  • Wingtip

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