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O: Fachverband Oberflächenphysik
O 11: Surface Reactions
O 11.6: Talk
Monday, March 27, 2023, 16:15–16:30, CHE 91
On-surface synthesis of enetriynes — Nan Cao1,2, •Biao Yang1, Alexander Riss1, Johanna Rosen2, Jonas Björk2, and Johannes V. Barth1 — 1Physics Department E20, Technical University of Munich, Garching, Germany — 2Department of Physics, Chemistry and Biology, IFM, Linköping University, Linköping, Sweden
Belonging to the enyne family, enetriynes comprise a distinct electron-rich all-carbon bonding scheme. However, the lack of convenient synthesis protocols limits the associated application potential within, e.g., biochemistry and materials science. Herein we introduce a pathway for highly selective enetriyne formation via tetramerization of terminal alkynes on a Ag(100) surface. Taking advantage of a directing hydroxyl group, we steer molecular assembly and reaction processes. Induced by O2 exposure the terminal alkyne moieties deprotonate and organometallic bis-acetylide dimer arrays evolve. Upon subsequent thermal annealing tetrameric enetriyne-bridged compounds are generated in high yield, readily self-assembling into regular networks. We combine high-resolution scanning probe microscopy, X-ray photoelectron spectroscopy and density functional theory calculations to examine the structural features, bonding characteristics and the underlying reaction mechanism. Our study provides an integrated strategy to precisely fabricated functional enetriyne species, providing access to a distinct class of highly conjugated π-system compounds.