On-Surface Cyclization of ortho-Dihalotetracenes to Four- and Six-Membered Rings.
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-m...
| Publicado en: | Journal of the American Chemical Society Vol. 139; no. 48; pp. 17617 - 17624 |
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| Autores principales: | , , , , , , , , , |
| Formato: | Artículo |
| Publicado: |
American Chemical Society
12/6/2017
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| Materias: | |
| Acceso en línea: | Ver este registro en EBSCOhost |
| fields | @attributes: recordID: 1 pdfLink: plink: https://search.ebscohost.com/login.aspx?direct=true&db=hlh&AN=126761824&site=ehost-live header: @attributes: shortDbName: hlh uiTerm: 126761824 longDbName: Humanities International Complete uiTag: AN controlInfo: bkinfo: jinfo: jid: 00027863 ACS jtl: Journal of the American Chemical Society issn: 00027863 maglogo: N pubinfo: dt: 12/6/2017 vid: 139 iid: 48 pid: 997 pub: American Chemical Society artinfo: ui: 126761824 10.1021/jacs.7b10026 ppf: 17617 ppct: 7 formats: tig: atl: On-Surface Cyclization of ortho-Dihalotetracenes to Four- and Six-Membered Rings. aug: au: Sánchez-Sánchez, Carlos Nicolaï, Adrien Rossel, Frédéric Jinming Cai Junzhi Liu Xinliang Feng Müllen, Klaus Ruffieux, Pascal Fasel, Roman Meunier, Vincent affil: Empa, Swiss Federal Laboratories for Materials Science and Technology, Überlandstrasse 129, CH-8600 Dübendorf, Switzerland Instituto de Ciencia de Materiales de Madrid (ICMM-CSIC), Sor Juana Inés de la Cruz 3, 28049 Madrid, Spain Department of Physics, Applied Physics, and Astronomy, Rensselaer Polytechnic Institute, Troy, New York 12180, United States Laboratoire Interdisciplinaire Carnot de Bourgogne UMR 6303 CNRS-Université de Bourgogne Franche-Comté, 9 Avenue Alain Savary, BP 47870, F-21078 Dijon Cedex, France. School of Materials Science and Engineering, Kunming University of Science and Technology, 650500 Kunming, China Center for Advancing Electronics Dresden & Department of Chemistry and Food Chemistry, Technische Universität Dresden, D-01062 Dresden, Germany Max Planck Institut for Polymer Research, Ackermannweg 10, 55128 Mainz, Germany Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, CH-3012 Bern, Switzerland su: Ring formation (Chemistry) Silver catalysts Density functional theory Scanning tunneling microscopy Nanoribbons Photopolymerization sug: subj: Ring formation (Chemistry) Silver catalysts Density functional theory Scanning tunneling microscopy Nanoribbons Photopolymerization ab: 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. pubtype: Academic Journal doctype: Article src: R language: English refInfo: copyright: @attributes: flag: Y dt: @attributes: year: 2017 holdings: @attributes: islocal: N |
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