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  • Lyu, YuanhaoChinese Acad Sci, Peoples R China; Univ Chinese Acad Sci, Peoples R China (author)

Unraveling Enyne Bonding via Dehydrogenation-Hydrogenation Processes in On-Surface Synthesis with Terminal Alkynes

  • Article/chapterEnglish2024

Publisher, publication year, extent ...

  • 2024
  • WILEY,2024
  • printrdacarrier

Numbers

  • LIBRIS-ID:oai:DiVA.org:liu-202913
  • https://urn.kb.se/resolve?urn=urn:nbn:se:liu:diva-202913URI
  • https://doi.org/10.1002/admi.202400222DOI

Supplementary language notes

  • Language:English
  • Summary in:English

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  • Subject category:ref swepub-contenttype
  • Subject category:art swepub-publicationtype

Notes

  • Funding Agencies|National Natural Science Foundation of China [12174431, 1192780039]; Strategic Priority Research Program of the Chinese Academy of Sciences [XDB30000000]; Swedish Research Council [2022-06725]; Swedish Government Strategic Research Area in Materials Science on Functional Materials at Linkoeping University (Faculty Grant SFO-Mat-LiU) [2009-00971]; German Research Foundation (DFG); European Union [847471]; DFG Excellence Cluster e-conversion; Munich Quantum Center
  • On-surface reactions of terminal alkynes in ultrahigh vacuum have attracted widespread attention due to their high technological promise. However, employing different precursors and substrate materials often intricate reaction schemes appear far from being well-understood. Thus, recent investigations of alkyne coupling on noble metal surfaces suggest non-dehydrogenative scenarios, contradicting earlier reports. Herein, the study employs noncontact atomic force microscopy (nc-AFM) with high spatial resolution to conclusively characterize exemplary alkyne coupling products. Contrary to initial interpretations proposing dehydrogenative homocoupling on Ag(111), bond-resolved AFM imaging reveals the expression of enyne motifs. Based on complementary, extensive density functional theory calculations, the pertaining reaction mechanisms are explored. It is proposed that enyne formation initiates with a direct carbon-carbon coupling between two alkyne groups, followed by surface-assisted dehydrogenation-hydrogenation processes. Thereby consecutive steps of atomic hydrogen cleavage, surface migration and recombination to a different carbon atom enable bridging via carbon-carbon double bonding. The new results shed light on subtle, but crucial surface-mediated hydrogen transfer processes involved in the chemical bond formation, which are suggested to be of general relevance in on-surface synthesis. Terminal alkyne coupling on Ag(111) in ultrahigh vacuum is conclusively examined by bond-resolved atomic force microscopy and density functional theory modeling. The prevailing bonding motif is the enyne moiety, originating from a distinct surface-mediated dehydrogenation-hydrogenation reaction pathway. The findings highlight the important role of hydrogen transfer in the course of on-surface synthesis procedures. image

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Added entries (persons, corporate bodies, meetings, titles ...)

  • Gao, FengChinese Acad Sci, Peoples R China; Univ Chinese Acad Sci, Peoples R China (author)
  • Cheng, PengChinese Acad Sci, Peoples R China; Univ Chinese Acad Sci, Peoples R China (author)
  • Chen, LanChinese Acad Sci, Peoples R China; Univ Chinese Acad Sci, Peoples R China; Songshan Lake Mat Lab, Peoples R China (author)
  • Klyatskaya, SvetlanaKarlsruhe Inst Technol KIT, Germany (author)
  • Ruben, MarioKarlsruhe Inst Technol KIT, Germany; Univ Strasbourg, France (author)
  • Rosén, JohannaLinköpings universitet,Materialdesign,Tekniska fakulteten(Swepub:liu)johro07 (author)
  • Barth, Johannes V.Tech Univ Munich, Germany (author)
  • Björk, JonasLinköpings universitet,Materialdesign,Tekniska fakulteten(Swepub:liu)jonbj66 (author)
  • Wu, KehuiChinese Acad Sci, Peoples R China; Univ Chinese Acad Sci, Peoples R China; Songshan Lake Mat Lab, Peoples R China (author)
  • Zhang, Yi-QiChinese Acad Sci, Peoples R China (author)
  • Chinese Acad Sci, Peoples R China; Univ Chinese Acad Sci, Peoples R ChinaChinese Acad Sci, Peoples R China; Univ Chinese Acad Sci, Peoples R China; Songshan Lake Mat Lab, Peoples R China (creator_code:org_t)

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  • In:Advanced Materials Interfaces: WILEY2196-7350

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