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

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

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60 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)17617-17623
Number of pages7
JournalJournal of the American Chemical Society
Volume139
Issue number48
DOIs
StatePublished - Dec 6 2017

All Science Journal Classification (ASJC) codes

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry

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