Flexible NO2 -Functionalized N-Heterocyclic Carbene Monolayers on Au (111) Surface

Shahar Dery, Suhong Kim, Gabriele Tomaschun, David Haddad, Albano Cossaro, Alberto Verdini, Luca Floreano, Thorsten Klüner, F. Dean Toste, Elad Gross

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35 Scopus citations


The formation of flexible self-assembled monolayers (SAMs) in which an external trigger modifies the geometry of surface-anchored molecules is essential for the development of functional materials with tunable properties. In this work, it is demonstrated that NO2 -functionalized N-heterocyclic carbene molecules (NHCs), which were anchored on Au (111) surface, change their orientation from tilted into flat-lying position following trigger-induced reduction of their nitro groups. DFT calculations identified that the energetic driving force for reorientation was the lower steric hindrance and stronger interactions between the chemically reduced NHCs and the Au surface. The trigger-induced changes in the NHCs' anchoring geometry and chemical functionality modified the work function and the hydrophobicity of the NHC-decorated Au surface, demonstrating the impact of a chemically tunable NHC-based SAM on the properties of the metal surface.

Original languageAmerican English
Pages (from-to)15067-15072
Number of pages6
JournalChemistry - A European Journal
Issue number66
StatePublished - 27 Nov 2019

Bibliographical note

Publisher Copyright:
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.


  • N-heterocyclic carbene
  • monolayers
  • surface chemistry


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