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Open Access Publications from the University of California

Noncovalent Dimerization after Enediyne Cyclization on Au(111)

  • Author(s): De Oteyza, DG
  • Pérez Paz, A
  • Chen, YC
  • Pedramrazi, Z
  • Riss, A
  • Wickenburg, S
  • Tsai, HZ
  • Fischer, FR
  • Crommie, MF
  • Rubio, A
  • et al.

© 2016 American Chemical Society. 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-C5cyclization pathway. On Au(111), we find that the C1-C5cyclization is suppressed and that the C1-C6cyclization yields a highly strained bicyclic olefin whose surface chemistry was hitherto unknown. The C1-C6product 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.

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