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

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Larrea_2017_CPC_N_heterocyclic_CCBY_VoR.pdf (1.093Mb)
Date
21/12/2017
Author
Larrea, Christian Rodriguez
Baddeley, Christopher John
Narouz, Mina R.
Mosey, Nicholas J.
Horton, J. Hugh
Crudden, Cathleen M.
Keywords
N-heterocyclic carbenes
Copper
Self assembled monolayers
Orientation
Wingtip
QC Physics
QD Chemistry
NDAS
BDC
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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.
Citation
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
Publication
ChemPhysChem
Status
Peer reviewed
DOI
https://doi.org/10.1002/cphc.201701045
ISSN
1439-4235
Type
Journal article
Rights
© 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.
Description
Funding: EPSRC PhD studentship (EP/M506631/1).
Collections
  • University of St Andrews Research
URI
http://hdl.handle.net/10023/12380

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