Room-Temperature C-C σ-Bond Activation of Biphenylene Derivatives on Cu(111)

Jan Patrick Calupitan, Tao Wang, Alejandro Pérez Paz, Berta Álvarez, Alejandro Berdonces-Layunta, Paula Angulo-Portugal, Rodrigo Castrillo-Bodero, Frederik Schiller, Diego Peña, Martina Corso, Dolores Pérez, Dimas G. de Oteyza

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)


Activating the strong C-C σ-bond is a central problem in organic synthesis. Directly generating activated C centers by metalation of structures containing strained four-membered rings is one maneuver often employed in multistep syntheses. This usually requires high temperatures and/or precious transition metals. In this paper, we report an unprecedented C-C σ-bond activation at room temperature on Cu(111). By using bond-resolving scanning probe microscopy, we show the breaking of one of the C-C σ-bonds of a biphenylene derivative, followed by insertion of Cu from the substrate. Chemical characterization of the generated species was complemented by X-ray photoemission spectroscopy, and their reactivity was explained by density functional theory calculations. To gain further insight into this unique reactivity on other coinage metals, the reaction pathway on Ag(111) was also investigated and the results were compared with those on Cu(111). This study offers new synthetic routes that may be employed in the in situ generation of activated species for the on-surface synthesis of novel C-based nanostructures.

Original languageEnglish
Pages (from-to)947-953
Number of pages7
JournalJournal of Physical Chemistry Letters
Issue number4
Publication statusPublished - Feb 2 2023

ASJC Scopus subject areas

  • General Materials Science
  • Physical and Theoretical Chemistry


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