Noncovalent Dimerization after Enediyne Cyclization on Au(111)

Dimas G. De Oteyza, Alejandro Pérez Paz, Yen Chia Chen, Zahra Pedramrazi, Alexander Riss, Sebastian Wickenburg, Hsin Zon Tsai, Felix R. Fischer, Michael F. Crommie, Angel Rubio

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)


We investigate the thermally induced cyclization of 1,2-bis(2-phenylethynyl)benzene on Au(111) using scanning tunneling microscopy and computer simulations. Cyclization of sterically hindered enediynes is known to proceed via two competing mechanisms in solution: a classic C1-C6 (Bergman) or a C1-C5 cyclization pathway. On Au(111), we find that the C1-C5 cyclization is suppressed and that the C1-C6 cyclization yields a highly strained bicyclic olefin whose surface chemistry was hitherto unknown. The C1-C6 product self-assembles into discrete noncovalently bound dimers on the surface. The reaction mechanism and driving forces behind noncovalent association are discussed in light of density functional theory calculations.

Original languageEnglish
Pages (from-to)10963-10967
Number of pages5
JournalJournal of the American Chemical Society
Issue number34
Publication statusPublished - Aug 31 2016
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry


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