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

doi:10.1021/jacs.7b10026

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

Engineering Science and Mechanics

Research output: Contribution to journal › Article › peer-review

61 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 language	English (US)
Pages (from-to)	17617-17623
Number of pages	7
Journal	Journal of the American Chemical Society
Volume	139
Issue number	48
DOIs	https://doi.org/10.1021/jacs.7b10026
State	Published - Dec 6 2017

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/jacs.7b10026

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title = "On-Surface Cyclization of ortho-Dihalotetracenes to Four- and Six-Membered Rings",

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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T1 - On-Surface Cyclization of ortho-Dihalotetracenes to Four- and Six-Membered Rings

AU - Sánchez-Sánchez, Carlos

AU - Nicolaï, Adrien

AU - Rossel, Frédéric

AU - Cai, Jinming

AU - Liu, Junzhi

AU - Feng, Xinliang

AU - Müllen, Klaus

AU - Ruffieux, Pascal

AU - Fasel, Roman

AU - Meunier, Vincent

PY - 2017/12/6

Y1 - 2017/12/6

N2 - 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.

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.

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JF - Journal of the American Chemical Society

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ER -

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

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