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 E des=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.
Highlights
Self-assembled monolayers of N-heterocyclic carbenes (NHCs) on copper are reported
Seminal work by Siemeling[4] and Johnson[5] showed that NHCs bind to planar Au surfaces
Other studies of NHC films on Au have shown remarkable effects on work function,[12] and highly ordered structures can be imaged by low temperature scanning tunneling microscopy (STM).[7]
Summary
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.
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