N‐Heterocyclic Olefins on a Silicon Surface

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Abstract: The adsorption of N‐heterocyclic olefins (NHOs) on silicon is investigated in a combined scanning tunneling microscopy, X‐ray photoelectron spectroscopy, and density functional theory study. We find that both of the studied NHOs bind covalently, with ylidic character, to the silicon adatoms of the substrate and exhibit good thermal stability. The adsorption geometry strongly depends on the N‐substituents: for large N‐substituents, an upright adsorption geometry is favored, while a flat‐lying geometry is found for the NHO with smaller wingtips. These different geometries strongly influence the quality and properties of the obtained monolayers. The upright geometry leads to the formation of ordered monolayers, whereas the flat‐lying NHOs yield a mostly disordered, but denser, monolayer. The obtained monolayers both show large work function reductions, as the higher density of the flat‐lying monolayer is found to compensate for the smaller vertical dipole moments. Our findings offer new prospects in the design of tailor‐made ligand structures in organic electronics and optoelectronics, catalysis, and material science.

Standort
Deutsche Nationalbibliothek Frankfurt am Main
Umfang
Online-Ressource
Sprache
Englisch

Erschienen in
N‐Heterocyclic Olefins on a Silicon Surface ; day:09 ; month:11 ; year:2023 ; extent:11
Angewandte Chemie ; (09.11.2023) (gesamt 11)

Urheber
Das, Mowpriya
Hogan, Conor
Zielinski, Robert
Kubicki, Milan
Koy, Maximilian
Kosbab, Canan
Brozzesi, Simone
Das, Ankita
Nehring, Mike Thomas
Balfanz, Viktoria
Brühne, Juls
Dähne, Mario
Franz, Martin
Esser, Norbert
Glorius, Frank

DOI
10.1002/ange.202314663
URN
urn:nbn:de:101:1-2023111014124079061443
Rechteinformation
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
Letzte Aktualisierung
14.08.2025, 10:50 MESZ

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Beteiligte

  • Das, Mowpriya
  • Hogan, Conor
  • Zielinski, Robert
  • Kubicki, Milan
  • Koy, Maximilian
  • Kosbab, Canan
  • Brozzesi, Simone
  • Das, Ankita
  • Nehring, Mike Thomas
  • Balfanz, Viktoria
  • Brühne, Juls
  • Dähne, Mario
  • Franz, Martin
  • Esser, Norbert
  • Glorius, Frank

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