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- Title
Terminal Alkyne Coupling on a Corrugated Noble Metal Surface: From Controlled Precursor Alignment to Selective Reactions.
- Authors
Lin, Tao; Zhang, Liding; Björk, Jonas; Chen, Zhi; Ruben, Mario; Barth, Johannes V.; Klappenberger, Florian
- Abstract
Surface-templated covalent coupling of organic precursors currently emerges as a promising route to the atom-precise fabrication of low-dimensional carbon materials. Here, we investigate the adsorption and the coupling reactions of 4,4 ′′-diethynyl-1,1 ′:4 ′,1 ′′-terphenyl on Au(110) under ultra-high vacuum conditions by using scanning tunneling microscopy combined with density functional theory and kinetic Monte Carlo calculations. Temperature treatment induces both 1,2,4-asymmetric cyclotrimerization and homocoupling, resulting in various reaction products, including a previously unreported, surface-templated H-shaped pentamer. Our analysis of the temperature-dependent relative product abundances unravels that 1,2,4-trimerization and homocoupling proceed via identical intermediate species with the final products depending on the competition of coupling to a third monomer versus dehydrogenation. Our study sheds light on the control of coupling reactions by corrugated surfaces and annealing protocols.
- Subjects
ALKYNES; PRECIOUS metals; COUPLING reactions (Chemistry); CHEMICAL precursors; DENSITY functional theory; SCANNING tunneling microscopy
- Publication
Chemistry - A European Journal, 2017, Vol 23, Issue 62, p15588
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201701735