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

Date publication

décembre 2017

Journal

Journal of the American Chemical Society

Auteurs

Membres identifiés du Cancéropôle Est :
Dr NICOLAI Adrien

Tous les auteurs :
Sánchez-Sánchez C, Nicolaï A, Rossel F, Cai J, Liu J, Feng X, Müllen K, Ruffieux P, Fasel R, Meunier V

Lien Pubmed

https://www.ncbi.nlm.nih.gov/pubmed/29112817

Résumé

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.

Référence

J Am Chem Soc. 2017 12 6;139(48):17617-17623