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On-surface cyclization of ortho-dihalotetracenes to four- and six-membered rings

AuthorsSánchez, Carlos ; Nicolaï, Adrien; Rossel, Frédéric; Cai, Jinming; Liu, Junzhi; Feng, Xinliang; Müllen, Klaus; Ruffieux, Pascal; Fasel, Roman; Meunier, Vincent
Issue Date6-Dec-2017
PublisherAmerican Chemical Society
CitationJournal of the American Chemical Society 139(48): 17617-17623 (2017)
AbstractWe 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.
Publisher version (URL)https://doi.org/10.1021/jacs.7b10026
Identifiersdoi: 10.1021/jacs.7b10026
issn: 0002-7863
e-issn: 1520-5126
Appears in Collections:(ICMM) Artículos
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