Regensburg 2022 – wissenschaftliches Programm
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O: Fachverband Oberflächenphysik
O 79: Surface Reactions and Heterogeneous Catalysis 3
O 79.2: Vortrag
Freitag, 9. September 2022, 11:00–11:15, H4
On-surface cyclomerization of oxygen heterocycles: Controlling the ring size by tuning the molecule-surface interaction — •Andreas Dörr1, Nemanja Kocic1, Lukas Fromm2, Vladimir Akhmetov3, Konstantin Y. Amsharov3, Andreas Görling2, and Sabine Maier1 — 1Department of Physics, Friedrich-Alexander-Universität Erlangen-Nürnberg, 91058 Erlangen (Germany) — 2Department of Chemistry and Pharmacy, Chair of Theoretical Chemistry, Friedrich-Alexander-Universität Erlangen-Nürnberg, 91058 Erlangen (Germany) — 3Institute for Chemistry, Martin-Luther-University Halle-Wittenberg, 06099 Halle (Germany)
Heterocycles with nitrogen, oxygen, or sulfur atoms are the basic units that incorporate chemical functionalization into carbon scaffolds. For oxygen-doped nanographenes, furan and pyran, having five- and six-membered rings, respectively, are the most common ones. However, their on-surface synthesis via cyclomerization reactions has so far been elusive. Here, we present a low-temperature scanning tunneling microscopy study combined with density functional theory calculations to understand the on-surface synthesis of furan and pyran derivatives from ketone-functionalized precursors on metal surfaces. We first discuss the self-assemblies of the precursors, which are strongly influenced by molecule-surface interactions. Upon annealing, the different intermolecular binding motifs resulted in selective cyclomerization reactions toward furan and pyran moieties.