N-heterocyclic carbene self-assembled monolayers on copper and gold : dramatic effect of wingtip groups on binding, orientation and assembly
MetadataShow full item record
Altmetrics Handle Statistics
Altmetrics DOI Statistics
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.
Larrea , C R , Baddeley , C J , Narouz , M R , Mosey , N J , Horton , J H & Crudden , C M 2017 , ' N -heterocyclic carbene self-assembled monolayers on copper and gold : dramatic effect of wingtip groups on binding, orientation and assembly ' , ChemPhysChem , vol. 18 , no. 24 , pp. 3536–3539 . https://doi.org/10.1002/cphc.201701045
© 2017 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
DescriptionFunding: EPSRC PhD studentship (EP/M506631/1).
Items in the St Andrews Research Repository are protected by copyright, with all rights reserved, unless otherwise indicated.