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Published February 6, 2019 | Version v1
Journal article Open

Coordination-Controlled C–C Coupling Products via ortho-Site C–H Activation

  • 1. Key Laboratory for the Physics and Chemistry of Nanodevices, Department of Electronics, Peking University, Beijing 100871, China
  • 2. Peking University Information Technology Institute (Tianjin Binhai), Tianjin 300450, China
  • 3. Department of Physics, Friedrich-Alexander University Erlangen-Nürnberg
  • 4. Institute for Solid State Physics and Optics, Wigner Research Center for Physics, Hungarian Academy of Sciences, H-1525 Budapest, Hungary

Description

The coordination-restricted ortho-site C−H bond activation and dehydrogenative homocoupling of 4,4′-(1,3-phenylene)dipyridine (1,3-BPyB) and 4,4′-(1,4-phenylene)dipyridine (1,4-BPyB) on different metal surfaces were studied by a combination of scanning tunneling microscopy, noncontact atomic force microscopy,
and density functional theory calculations. The coupling products on Cu(111) exhibited certain configurations subject to the spatial restriction of robust two-fold Cu−N coordination bonds. Compared to the V-shaped 1,3-BPyB, the straight backbone of 1,4-BPyB helped to further reduce the variety of reactive products. By utilizing the
three-fold coordination of Fe atoms with 1,4-BPyB molecules on Au(111), a large-scale network containing single products was constructed. Our results offer a promising protocol for controllable on-surface synthesis with the aid of robust coordination interactions.

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Additional details

Funding

SURFLINK – MOLECULAR CARPETS ON INSULATING SURFACES: RATIONAL DESIGN OF COVALENT NETWORKS 637831
European Commission