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Highly stereospecific on-surface dimerization into bishelicenes: Topochemical Ullmann coupling of bromohelicene on Au(111)
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SYSNO ASEP 0582135 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Highly stereospecific on-surface dimerization into bishelicenes: Topochemical Ullmann coupling of bromohelicene on Au(111) Author(s) Voigt, J. (CH)
Martin, K. (FR)
Neziri, E. (CH)
Baljozović, M. (CH)
Wäckerlin, C. (CH)
Avarvari, N. (FR)
Ernst, Karl-Heinz (FZU-D) ORCIDNumber of authors 7 Article number e202300134 Source Title Chemistry - A European Journal. - : Wiley - ISSN 0947-6539
Roč. 29, č. 28 (2023)Number of pages 4 s. Language eng - English Country DE - Germany Keywords chirality ; helicenes ; on-surface chemistry ; polyaromatic hydrocarbons ; scanning tunneling microscopy Subject RIV BM - Solid Matter Physics ; Magnetism OECD category Condensed matter physics (including formerly solid state physics, supercond.) R&D Projects GX20-13692X GA ČR - Czech Science Foundation (CSF) GF21-17194L GA ČR - Czech Science Foundation (CSF) Method of publishing Open access Institutional support FZU-D - RVO:68378271 UT WOS 000956792100001 EID SCOPUS 85150761045 DOI 10.1002/chem.202300134 Annotation The on-surface dimerization into bis(hexahelicene) on a gold(111) surface has been studied by means of scanning tunneling microscopy and time-of-flight secondary mass spectrometry. C!C Ullmann coupling of (rac)-2-bromohexahelicene leads to formation of the (M,M)- and (P,P)- diastereomers of 2,2’-bis(hexahelicene), whilst formation of the (M,P)-diastereomer is not observed. Upon cooling, the bis(hexahelicene) aggregates into an ordered two-dimensional lattice with partly randomly distributed enantiomers. The highly specific diastereomeric coupling is explained by the surface alignment of educt in combination with the strong steric overcrowding in a possible surface-confined (M,P)-product.
Workplace Institute of Physics Contact Kristina Potocká, potocka@fzu.cz, Tel.: 220 318 579 Year of Publishing 2024 Electronic address https://hdl.handle.net/11104/0350210
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