Strong Metal-Adsorbate Interactions Increase the Reactivity and Decrease the Orientational Order of OH-Functionalized N-Heterocyclic Carbene Monolayers

Shahar Dery, Iris Berg, Suhong Kim, Albano Cossaro, Alberto Verdini, Luca Floreano, F. Dean Toste, Elad Gross*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

23 Scopus citations

Abstract

Fundamental understanding of the correlation between the structure and reactivity of chemically addressable N-heterocyclic carbene (NHC) molecules on various surfaces is essential for the design of functional NHC-based self-assembled monolayers. In this work, we identified the ways by which the deposition of chemically addressable OH-NHCs on Au(111) or Pt(111) surfaces modified the anchoring geometry and chemical reactivity of surface-anchored NHCs. The properties of surface-anchored NHCs were probed by conducting X-ray photoelectron spectroscopy and polarized near-edge X-ray absorption fine structure measurements. While no preferred orientation was identified for OH-NHCs on Pt(111), the anchored molecules adopted a preferred flat-lying position on Au(111). Dehydrogenation and aromatization of the imidazoline ring along with partial hydroxyl oxidation were detected in OH-NHCs that were anchored on Au(111). The dehydrogenation and aromatization reactions were facilitated, along with partial decomposition, for OH-NHCs that were anchored on Pt(111). The spectroscopic results reveal that stronger metal-adsorbate interactions increase the reactivity of surface-anchored OH-NHCs while decreasing their molecular orientational order.

Original languageAmerican English
Pages (from-to)697-703
Number of pages7
JournalLangmuir
Volume36
Issue number3
DOIs
StatePublished - 28 Jan 2020

Bibliographical note

Publisher Copyright:
© 2019 American Chemical Society.

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