Diacetylene Linked Anthracene Oligomers Synthesized by One-Shot Homocoupling of Trimethylsilyl on Cu(111)

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Diacetylene Linked Anthracene Oligomers Synthesized by One-Shot Homocoupling of Trimethylsilyl on Cu(111). / Kawai, Shigeki; Krejci, Ondrej; Foster, Adam; Pawlak, Rémy; Xu, Feng; Peng, Lifen; Orita, Akihiro; Meyer, Ernst.

In: ACS Nano, Vol. 12, No. 8, 07.08.2018, p. 8791−8797.

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Kawai, Shigeki ; Krejci, Ondrej ; Foster, Adam ; Pawlak, Rémy ; Xu, Feng ; Peng, Lifen ; Orita, Akihiro ; Meyer, Ernst. / Diacetylene Linked Anthracene Oligomers Synthesized by One-Shot Homocoupling of Trimethylsilyl on Cu(111). In: ACS Nano. 2018 ; Vol. 12, No. 8. pp. 8791−8797.

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@article{961e3e208def4680b1c3db7a4c6c753c,
title = "Diacetylene Linked Anthracene Oligomers Synthesized by One-Shot Homocoupling of Trimethylsilyl on Cu(111)",
abstract = "On-surface chemical reaction has become a very powerful technique to conjugate small precursor molecules and several reactions have been proposed with the aim to fabricate functional nanostructures on surfaces. Here we present an unforeseen adsorption mode of 9,10-bis-((trimethylsilyl)ethynyl)anthracene on a Cu(111)surface and the resulting one-shot desilylative homocoupling of of the adsorbate by annealing at 400 K. With a combination of high-resolution atomic force microscopy and density functional theory calculations, we found that the triple bonds and silicon atoms of the monomer chemically interact with the copper surface. After the oligomerization, we discovered that the anthracene units are linked to each other via buta-1,3-diynediyl fragments while keeping the surface clean. Furthermore, the force measurement revealed the chemical nature at the center of anthracene unit.",
keywords = "on-surface chemical reaction, Glaser coupling, trimethylsilyl, anthracene, atomic force microscopy",
author = "Shigeki Kawai and Ondrej Krejci and Adam Foster and R{\'e}my Pawlak and Feng Xu and Lifen Peng and Akihiro Orita and Ernst Meyer",
year = "2018",
month = "8",
day = "7",
doi = "10.1021/acsnano.8b05116",
language = "English",
volume = "12",
pages = "8791−8797",
journal = "ACS Nano",
issn = "1936-0851",
publisher = "AMERICAN CHEMICAL SOCIETY",
number = "8",

}

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TY - JOUR

T1 - Diacetylene Linked Anthracene Oligomers Synthesized by One-Shot Homocoupling of Trimethylsilyl on Cu(111)

AU - Kawai, Shigeki

AU - Krejci, Ondrej

AU - Foster, Adam

AU - Pawlak, Rémy

AU - Xu, Feng

AU - Peng, Lifen

AU - Orita, Akihiro

AU - Meyer, Ernst

PY - 2018/8/7

Y1 - 2018/8/7

N2 - On-surface chemical reaction has become a very powerful technique to conjugate small precursor molecules and several reactions have been proposed with the aim to fabricate functional nanostructures on surfaces. Here we present an unforeseen adsorption mode of 9,10-bis-((trimethylsilyl)ethynyl)anthracene on a Cu(111)surface and the resulting one-shot desilylative homocoupling of of the adsorbate by annealing at 400 K. With a combination of high-resolution atomic force microscopy and density functional theory calculations, we found that the triple bonds and silicon atoms of the monomer chemically interact with the copper surface. After the oligomerization, we discovered that the anthracene units are linked to each other via buta-1,3-diynediyl fragments while keeping the surface clean. Furthermore, the force measurement revealed the chemical nature at the center of anthracene unit.

AB - On-surface chemical reaction has become a very powerful technique to conjugate small precursor molecules and several reactions have been proposed with the aim to fabricate functional nanostructures on surfaces. Here we present an unforeseen adsorption mode of 9,10-bis-((trimethylsilyl)ethynyl)anthracene on a Cu(111)surface and the resulting one-shot desilylative homocoupling of of the adsorbate by annealing at 400 K. With a combination of high-resolution atomic force microscopy and density functional theory calculations, we found that the triple bonds and silicon atoms of the monomer chemically interact with the copper surface. After the oligomerization, we discovered that the anthracene units are linked to each other via buta-1,3-diynediyl fragments while keeping the surface clean. Furthermore, the force measurement revealed the chemical nature at the center of anthracene unit.

KW - on-surface chemical reaction

KW - Glaser coupling

KW - trimethylsilyl

KW - anthracene

KW - atomic force microscopy

U2 - 10.1021/acsnano.8b05116

DO - 10.1021/acsnano.8b05116

M3 - Article

VL - 12

SP - 8791−8797

JO - ACS Nano

JF - ACS Nano

SN - 1936-0851

IS - 8

ER -

ID: 28771537