On-Surface Cyclization of ortho-Dihalotetracenes to Four- and Six-Membered Rings
Sanchez-Sanchez C, Nicolai A, Rossel F, Cai J, Liu J, Feng X, Muellen K, Ruffieux P, Fasel R, Meunier V (2017)
Publication Type: Journal article
Publication year: 2017
Journal
Book Volume: 139
Pages Range: 17617-17623
Journal Issue: 48
DOI: 10.1021/jacs.7b10026
Abstract
We report on the surface-catalyzed formal [2+2] and [2+2+2] cycloadditions of ortho-activated tetracene species on a Ag(111) substrate under ultrahigh vacuum conditions. Three different products are obtained: tetracene dimers, trimers, and tetramers. The former results from the formation of a four-membered ring while the other two arise from cyclization into six-membered rings. These on-surface reactions have been monitored by scanning tunneling microscopy and rationalized by density functional theory calculations. Our approach, based on the reaction of ortho-dihalo precursor monomers via formal cycloadditions, establishes an additional method for the highly active field of on-surface synthesis and enables the development of novel 1D and 2D covalent carbon nanostructures.
Involved external institutions
Eidgenössische Materialprüfungs- und Forschungsanstalt (Empa) / Swiss Federal Laboratories for Materials Science & Technology
Switzerland (CH)
Rensselaer Polytechnic Institute (RPI)
United States (USA) (US)
Technische Universität Dresden
Germany (DE)
Max-Planck-Institut für Polymerforschung (MPI-P) / Max Planck Institute for Polymer Research
Germany (DE)
Switzerland (CH)
Rensselaer Polytechnic Institute (RPI)
United States (USA) (US)
Technische Universität Dresden
Germany (DE)
Max-Planck-Institut für Polymerforschung (MPI-P) / Max Planck Institute for Polymer Research
Germany (DE)
How to cite
APA:
Sanchez-Sanchez, C., Nicolai, A., Rossel, F., Cai, J., Liu, J., Feng, X.,... Meunier, V. (2017). On-Surface Cyclization of ortho-Dihalotetracenes to Four- and Six-Membered Rings. Journal of the American Chemical Society, 139(48), 17617-17623. https://doi.org/10.1021/jacs.7b10026
MLA:
Sanchez-Sanchez, Carlos, et al. "On-Surface Cyclization of ortho-Dihalotetracenes to Four- and Six-Membered Rings." Journal of the American Chemical Society 139.48 (2017): 17617-17623.
BibTeX: Download