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Noncovalent Dimerization after Enediyne Cyclization on Au(111).

  • Author(s): de Oteyza, Dimas G;
  • Pérez Paz, Alejandro;
  • Chen, Yen-Chia;
  • Pedramrazi, Zahra;
  • Riss, Alexander;
  • Wickenburg, Sebastian;
  • Tsai, Hsin-Zon;
  • Fischer, Felix R;
  • Crommie, Michael F;
  • Rubio, Angel
  • et al.

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 C(1)-C(6) (Bergman) or a C(1)-C(5) cyclization pathway. On Au(111), we find that the C(1)-C(5) cyclization is suppressed and that the C(1)-C(6) cyclization yields a highly strained bicyclic olefin whose surface chemistry was hitherto unknown. The C(1)-C(6) 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.

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