Open AccessOn-Surface Cyclization of ortho-Dihalotetracenes to Four- and Six-Membered Rings
Author(s) -
Carlos SánchezSánchez,
Adrien Nicolaı̈,
F. Rossel,
Jinming Cai,
Junzhi Liu,
Xinliang Feng,
Kläus Müllen,
Pascal Ruffieux,
Román Fasel,
Vincent Meunier
Publication year - 2017
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/jacs.7b10026
Subject(s) - tetracene , chemistry , scanning tunneling microscope , covalent bond , substrate (aquarium) , ring (chemistry) , density functional theory , monomer , molecule , stereochemistry , crystallography , computational chemistry , nanotechnology , organic chemistry , materials science , oceanography , geology , polymer
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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