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Intramolecular Coupling of Terminal Alkynes by Atom Manipulation
Author(s) -
Albrecht Florian,
Rey Dulce,
Fatayer Shadi,
Schulz Fabian,
Pérez Dolores,
Peña Diego,
Gross Leo
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202009200
Subject(s) - intramolecular force , scanning tunneling microscope , chemistry , density functional theory , molecule , alkyne , coupling (piping) , coupling reaction , atom (system on chip) , crystallography , computational chemistry , stereochemistry , nanotechnology , materials science , catalysis , organic chemistry , computer science , metallurgy , embedded system
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.