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001044874 1001_ $$00000-0002-3804-4573$$aRuan, Zilin$$b0$$eFirst author
001044874 245__ $$aHighly Structure‐Selective On‐Surface Synthesis of Isokekulene Versus Kekulene
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001044874 520__ $$aThe 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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001044874 536__ $$0G:(GEPRIS)511561801$$aDFG project G:(GEPRIS)511561801 - Manipulierung von 2D Supraleitung und Majorana Zuständen auf der Nanoskala (511561801)$$c511561801$$x2
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001044874 7001_ $$00000-0002-2629-6212$$aFan, Qitang$$b1
001044874 7001_ $$00009-0001-8189-3853$$aReichmann, Alexander$$b2
001044874 7001_ $$00009-0004-8781-3035$$aKang, Faming$$b3
001044874 7001_ $$0P:(DE-HGF)0$$aNaumann, Tim$$b4
001044874 7001_ $$0P:(DE-HGF)0$$aWerner, Simon$$b5
001044874 7001_ $$00009-0008-5658-5729$$aKleykamp, Olaf$$b6
001044874 7001_ $$0P:(DE-Juel1)177811$$aMartinez-Castro, Jose$$b7
001044874 7001_ $$0P:(DE-Juel1)162163$$aLüpke, Felix$$b8
001044874 7001_ $$0P:(DE-Juel1)174294$$aHaags, Anja$$b9
001044874 7001_ $$0P:(DE-Juel1)167128$$aBocquet, François C.$$b10
001044874 7001_ $$0P:(DE-Juel1)128774$$aKumpf, Christian$$b11
001044874 7001_ $$0P:(DE-Juel1)128790$$aSoubatch, Serguei$$b12
001044874 7001_ $$00000-0001-8244-8201$$aSundermeyer, Jörg$$b13
001044874 7001_ $$00000-0002-8057-7795$$aPuschnig, Peter$$b14
001044874 7001_ $$0P:(DE-Juel1)128791$$aTautz, F. Stefan$$b15
001044874 7001_ $$00000-0001-5579-2568$$aGottfried, J. Michael$$b16
001044874 7001_ $$0P:(DE-Juel1)190628$$aWenzel, Sabine$$b17$$eCorresponding author
001044874 773__ $$0PERI:(DE-600)2011836-3$$a10.1002/anie.202509932$$gp. e202509932$$n36$$pe202509932$$tAngewandte Chemie / International edition$$v64$$x1433-7851$$y2025
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