Kavli Affiliate: Michael F. Crommie
| First 5 Authors: Dimas G. de Oteyza, Alejandro Pérez Paz, Yen-Chia Chen, Zahra Pedramrazi, Alexander Riss
| Summary:
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 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 non-covalently bound dimers on the surface. The
reaction mechanism and driving forces behind non-covalent association are
discussed in light of density functional theory calculations.
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