Non-Covalent Dimerization after Enediyne Cyclization on Au(111)
- Resource Type
- Working Paper
- Authors
- de Oteyza, Dimas G.; Paz, Alejandro Pérez; Chen, Yen-Chia; Pedramrazi, Zahra; Riss, Alexander; Wickenburg, Sebastian; Tsai, Hsin-Zon; Fischer, Felix R.; Crommie, Michael F.; Rubio, Angel
- Source
- J. Am. Chem. Soc. 2016, 138, 10963-10967
- Subject
- Condensed Matter - Materials Science
- Language
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.