Noncovalent Dimerization after Enediyne Cyclization on Au(111)

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

doi:10.1021/jacs.6b05203

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Noncovalent Dimerization after Enediyne Cyclization on Au(111)

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Rubio, Angel
Nano-Bio Spectroscopy Group and ETSF, Universidad del País Vasco, CFM CSIC-UPV/EHUMPC, 20018 San Sebastián, Spain;
Theory Group, Theory Department, Max Planck Institute for the Structure and Dynamics of Matter, Max Planck Society;
Center for Free-Electron Laser Science (CFEL), Luruper Chaussee 149, 22761 Hamburg, Germany;

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Citation

de Oteyza, D. G., Paz, A. P., Chen, Y.-C., Pedramrazi, Z., Riss, A., Wickenburg, S., et al. (2016). Noncovalent Dimerization after Enediyne Cyclization on Au(111). Journal of the American Chemical Society, 138(34), 10963-10967. doi:10.1021/jacs.6b05203.

Cite as: https://hdl.handle.net/11858/00-001M-0000-002B-1BA0-B

Abstract

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.