Elucidating the influence of anchoring geometry on the reactivity of NO 2 -functionalized N-heterocyclic carbene monolayers

We demonstrated that the chemical reactivity of surface-anchored NO2-functionalized NHCs (NO2–NHCs) can be tuned by modifying the distance between the functional group and the reactive surface, which is governed by the deposition technique.
S. Dery et al., DOI:10.1021/acs.jpclett.9b01808
Reactivity of carbene

The exceptional chemical tunability and metal affinity of N-heterocyclic carbene molecules (NHCs) have enabled the formation of chemically-active NHC- based self-assembled monolayers (SAMs) in which the chemically-active groups reside in proximity to the metal surface. Herein, in-depth analysis of the influence of the deposition technique on the anchoring geometry, chemical reactivity, and thermal stability of the SAM was performed by using NO 2 -functionalized NHCs that were anchored on Pt (111). The properties of NO 2 -functionalized NHCs were identified by conducting X-ray photoelectron spectroscopy (XPS) and near-edge x-ray absorption fine structure (NEXAFS) measurements. These results demonstrate the impact of the distance between functional groups and the reactive surface on the reactivity of chemically addressable SAMs. The anchoring geometry is therefore identified as a crucial factor for the design of chemically addressable SAMs.

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Elucidating the Influence of Anchoring Geometry on the Reactivity of NO2-Functionalized N-Heterocyclic Carbene Monolayers, S. Dery, S. Kim, G. Tomaschun, I. Berg, D. Feferman, A. Cossaro, A. Verdini, L. Floreano, T. Klüner, F.D. Toste, E. Gross, J. Phys. Chem. Lett. 10, 17, 5099 (2019);DOI:10.1021/acs.jpclett.9b01808
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