Intramolecular Coupling of Terminal Alkynes by Atom Manipulation

Florian Albrecht, Dulce Rey, Shadi Fatayer, Fabian Schulz, Dolores Pérez, Diego Peña, Leo Gross

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

Abstract

Glaser-like coupling of terminal alkynes by thermal activation is extensively used in on-surface chemistry. Here we demonstrate an intramolecular version of this reaction performed by atom manipulation. We used voltage pulses from the tip to trigger a Glaser-like coupling between terminal alkyne carbons within a custom-synthesized precursor molecule adsorbed on bilayer NaCl on Cu(111). Different conformations of the precursor molecule and the product were characterized by molecular structure elucidation with atomic force microscopy and orbital density mapping with scanning tunneling microscopy, accompanied by density functional theory calculations. We revealed partially dehydrogenated intermediates, providing insight into the reaction pathway.
Original languageEnglish (US)
Pages (from-to)22989-22993
Number of pages5
JournalAngewandte Chemie - International Edition
Volume59
Issue number51
DOIs
StatePublished - Dec 14 2020
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis

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