Hauptseite > Publikationsdatenbank > Highly Structure‐Selective On‐Surface Synthesis of Isokekulene Versus Kekulene > print

001     1044874
005     20250930132705.0
024 7 _ |a 10.1002/anie.202509932
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100 1 _ |a Ruan, Zilin
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245 _ _ |a Highly Structure‐Selective On‐Surface Synthesis of Isokekulene Versus Kekulene
260 _ _ |a Weinheim
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520 _ _ |a The role of different facets of metal nanoparticles in steering reaction pathways is crucial for the design ofheterogeneous catalysts with superior selectivity. As a prominent class of reactions, transition-metal-catalyzed carbon-hydrogen (C─H) bond activation is widely used for the synthesis of base chemicals, modern organic materials, andpharmaceuticals. Here, we report orthogonal selectivity in intramolecular cyclodehydrogenation of a nonplanar cyclicprecursor steered by different facets of a copper single crystal. On the Cu(110) surface, the previously unknown cycloareneisokekulene forms with a high selectivity of 92%, whereas reaction on the Cu(111) surface exclusively yields kekulene(>99%). Combining scanning tunneling microscopy with CO-functionalized tips and density functional theory, we identifytwo adsorption geometries of the precursor, which react to the respective products. Isokekulene adopts two nonplanaradsorption configurations and exhibits strong molecule-substrate interactions, explaining its preferential formation onCu(110). This combined in-solution and on-surface synthesis approach represents an alternative route for the highlyselective synthesis of molecules that are challenging to synthesize and process via conventional methods.
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536 _ _ |a SFB 1083 A12 - Struktur und Anregungen von hetero-epitaktischen Schichtsystemen aus schwach wechselwirkenden 2D-Materialien und molekularen Schichten (A12) (385975694)
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536 _ _ |a DFG project G:(GEPRIS)511561801 - Manipulierung von 2D Supraleitung und Majorana Zuständen auf der Nanoskala (511561801)
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700 1 _ |a Fan, Qitang
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700 1 _ |a Reichmann, Alexander
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700 1 _ |a Kang, Faming
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700 1 _ |a Tautz, F. Stefan
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700 1 _ |a Wenzel, Sabine
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773 _ _ |a 10.1002/anie.202509932
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