N‐Heterocyclic Olefins on a Silicon Surface

Author:

Das Mowpriya1ORCID,Hogan Conor23ORCID,Zielinski Robert4ORCID,Kubicki Milan4ORCID,Koy Maximilian1ORCID,Kosbab Canan4,Brozzesi Simone3ORCID,Das Ankita1ORCID,Nehring Mike Thomas4,Balfanz Viktoria4,Brühne Juls4,Dähne Mario4ORCID,Franz Martin4ORCID,Esser Norbert45ORCID,Glorius Frank1ORCID

Affiliation:

1. Westfälische Wilhelms-Universität Münster Organisch-Chemisches Institut Corrensstrasse 40 48149 Münster Germany

2. Istituto di Struttura della Materia-CNR (ISM-CNR) Via del Fosso del Cavaliere 100 00133 Rome Italy

3. Dipartimento di Fisica Università di Roma ‘Tor Vergata' Via della Ricerca Scientifica 1 00133 Rome Italy

4. Technische Universität Berlin Institut für Festkörperphysik Hardenbergstrasse 36 D-10623 Berlin Germany

5. Leibniz-Institut für Analytische Wissenschaften – ISAS e.V. Schwarzschildstrasse 8 12489 Berlin Germany

Abstract

AbstractThe 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.

Funder

Deutsche Forschungsgemeinschaft

Ministerium für Kultur und Wissenschaft des Landes Nordrhein-Westfalen

Bundesministerium für Bildung und Forschung

Publisher

Wiley

Subject

General Chemistry,Catalysis

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