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

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Article
en
2019

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

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en
2019
Vol 36 (3)
Vol. 36
DOI: 10.1021/acs.langmuir.9b02401

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Dean Toste
Dean Toste

University of California, Berkeley

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Shahar Dery
Iris Berg
Suhong Kim
+5 more

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.

How to cite this publication

Shahar Dery, Iris Berg, Suhong Kim, Albano Cossaro, Alberto Verdini, Luca Floreano, Dean Toste, Elad Gross (2019). Strong Metal–Adsorbate Interactions Increase the Reactivity and Decrease the Orientational Order of OH-Functionalized N-Heterocyclic Carbene Monolayers. , 36(3), DOI: https://doi.org/10.1021/acs.langmuir.9b02401.

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Publication Details

Type

Article

Year

2019

Authors

8

Datasets

0

Total Files

0

Language

en

DOI

https://doi.org/10.1021/acs.langmuir.9b02401

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