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Sánchez-Sánchez C, Nicolaï A, Rossel F, et al. On-Surface Cyclization of ortho-Dihalotetracenes to Four- and Six-Membered Rings. J Am Chem Soc. 2017;139(48):17617-17623doi: 10.1021/jacs.7b10026.
Sánchez-Sánchez, C., Nicolaï, A., Rossel, F., Cai, J., Liu, J., Feng, X., Müllen, K., Ruffieux, P., Fasel, R., & 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
Sánchez-Sánchez, Carlos, et al. "On-Surface Cyclization of ortho-Dihalotetracenes to Four- and Six-Membered Rings." Journal of the American Chemical Society vol. 139,48 (2017): 17617-17623. doi: https://doi.org/10.1021/jacs.7b10026
Sánchez-Sánchez C, Nicolaï A, Rossel F, Cai J, Liu J, Feng X, Müllen K, Ruffieux P, Fasel R, Meunier V. On-Surface Cyclization of ortho-Dihalotetracenes to Four- and Six-Membered Rings. J Am Chem Soc. 2017 Dec 06;139(48):17617-17623. doi: 10.1021/jacs.7b10026. Epub 2017 Nov 22. PMID: 29112817.
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J Am Chem Soc. 2017 Dec 06;139(48):17617-17623. doi: 10.1021/jacs.7b10026. Epub 2017 Nov 22.

On-Surface Cyclization of ortho-Dihalotetracenes to Four- and Six-Membered Rings.

Journal of the American Chemical Society

Carlos Sánchez-Sánchez, Adrien Nicolaï, Frédéric Rossel, Jinming Cai, Junzhi Liu, Xinliang Feng, Klaus Müllen, Pascal Ruffieux, Roman Fasel, Vincent Meunier

Affiliations

  1. Empa, Swiss Federal Laboratories for Materials Science and Technology , Überlandstrasse 129, CH-8600 Dübendorf, Switzerland.
  2. Instituto de Ciencia de Materiales de Madrid (ICMM-CSIC) , Sor Juana Inés de la Cruz 3, 28049 Madrid, Spain.
  3. Department of Physics, Applied Physics, and Astronomy, Rensselaer Polytechnic Institute , Troy, New York 12180, United States.
  4. School of Materials Science and Engineering, Kunming University of Science and Technology , 650500 Kunming, China.
  5. Center for Advancing Electronics Dresden & Department of Chemistry and Food Chemistry, Technische Universität Dresden , D-01062 Dresden, Germany.
  6. Max Planck Institut for Polymer Research , Ackermannweg 10, 55128 Mainz, Germany.
  7. Department of Chemistry and Biochemistry, University of Bern , Freiestrasse 3, CH-3012 Bern, Switzerland.

PMID: 29112817 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.

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