Diacetylene linked anthracene oligomers synthesized by one-shot homocoupling of trimethylsilyl on Cu(111)

Shigeki Kawai; Ondrěj Krejčí; Adam S. Foster; Rémy Pawlak; Feng Xu; Lifen Peng; Akihiro Orita; Ernst Meyer

doi:10.1021/acsnano.8b05116

Diacetylene linked anthracene oligomers synthesized by one-shot homocoupling of trimethylsilyl on Cu(111)

Shigeki Kawai, Ondrěj Krejčí, Adam S. Foster, Rémy Pawlak, Feng Xu, Lifen Peng, Akihiro Orita, Ernst Meyer

Chemistry (Twin Cities)

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

37 Scopus citations

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.

Original language	English (US)
Pages (from-to)	8791-8797
Number of pages	7
Journal	ACS nano
Volume	12
Issue number	8
DOIs	https://doi.org/10.1021/acsnano.8b05116
State	Published - Aug 28 2018

Bibliographical note

Funding Information:
This work was supported in part by Japan Society for the Promotion of Science (JSPS) KAKENHI Grant Number 15K21765, JP18H04430 in Middle Molecular Strategy, JP15K05440, and JP18K05134, by the Swiss National Science Foundation, by the Swiss Nanoscience Institute, by COST action MP1303 “Understanding and Controlling nano and Mesoscale Friction”, and by the Okayama Prefecture Industrial Promotion Foundation and Grant for Promotion of OUS Research Projects. O.K. and A.S.F. have been supported by the Academy of Finland through its Centres of Excellence Program Project No. 915804, and by the World Premier International Research Center Initiative (WPI), MEXT, Japan. They acknowledge use of the CSC, Helsinki for computational resources. O.K. would like to thank to Aliaksandr V. Yakutovich for his help with the AFM simulations.

Funding Information:
This work was supported in part by Japan Society for the Promotion of Science (JSPS) KAKENHI Grant Number 15K21765 JP18H04430 in Middle Molecular Strategy, JP15K05440, and JP18K05134 by the Swiss National Science Foundation, by the Swiss Nanoscience Institute, by COST action MP1303 "Understanding and Controlling nano and Mesoscale Friction", and by the Okayama Prefecture Industrial Promotion Foundation and Grant for Promotion of OUS Research Projects. O.K. and A.S.F. have been supported by the Academy of Finland through its Centres of Excellence Program Project No. 915804, and by the World Premier International Research Center Initiative (WPI) MEXT, Japan. They acknowledge use of the CSC, Helsinki for computational resources. O.K. would like to thank to Aliaksandr V. Yakutovich for his help with the AFM simulations.

Publisher Copyright:
© 2018 American Chemical Society.

Keywords

Glaser coupling
anthracene
atomic force microscopy
on-surface chemical reaction
trimethylsilyl

Access

10.1021/acsnano.8b05116

OpenUrl availability

Full text

Cite this

@article{ce7129e9c24b48cf9f704509ad9c8dad,

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 = "Glaser coupling, anthracene, atomic force microscopy, on-surface chemical reaction, trimethylsilyl",

author = "Shigeki Kawai and Ondr{\v e}j Krej{\v c}{\'i} and Foster, {Adam S.} and R{\'e}my Pawlak and Feng Xu and Lifen Peng and Akihiro Orita and Ernst Meyer",

note = "Funding Information: This work was supported in part by Japan Society for the Promotion of Science (JSPS) KAKENHI Grant Number 15K21765, JP18H04430 in Middle Molecular Strategy, JP15K05440, and JP18K05134, by the Swiss National Science Foundation, by the Swiss Nanoscience Institute, by COST action MP1303 “Understanding and Controlling nano and Mesoscale Friction”, and by the Okayama Prefecture Industrial Promotion Foundation and Grant for Promotion of OUS Research Projects. O.K. and A.S.F. have been supported by the Academy of Finland through its Centres of Excellence Program Project No. 915804, and by the World Premier International Research Center Initiative (WPI), MEXT, Japan. They acknowledge use of the CSC, Helsinki for computational resources. O.K. would like to thank to Aliaksandr V. Yakutovich for his help with the AFM simulations. Funding Information: This work was supported in part by Japan Society for the Promotion of Science (JSPS) KAKENHI Grant Number 15K21765 JP18H04430 in Middle Molecular Strategy, JP15K05440, and JP18K05134 by the Swiss National Science Foundation, by the Swiss Nanoscience Institute, by COST action MP1303 {"}Understanding and Controlling nano and Mesoscale Friction{"}, and by the Okayama Prefecture Industrial Promotion Foundation and Grant for Promotion of OUS Research Projects. O.K. and A.S.F. have been supported by the Academy of Finland through its Centres of Excellence Program Project No. 915804, and by the World Premier International Research Center Initiative (WPI) MEXT, Japan. They acknowledge use of the CSC, Helsinki for computational resources. O.K. would like to thank to Aliaksandr V. Yakutovich for his help with the AFM simulations. Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

month = aug,

day = "28",

doi = "10.1021/acsnano.8b05116",

language = "English (US)",

volume = "12",

pages = "8791--8797",

journal = "ACS nano",

issn = "1936-0851",

publisher = "American Chemical Society",

number = "8",

}

TY - JOUR

T1 - Diacetylene linked anthracene oligomers synthesized by one-shot homocoupling of trimethylsilyl on Cu(111)

AU - Kawai, Shigeki

AU - Krejčí, Ondrěj

AU - Foster, Adam S.

AU - Pawlak, Rémy

AU - Xu, Feng

AU - Peng, Lifen

AU - Orita, Akihiro

AU - Meyer, Ernst

N1 - Funding Information: This work was supported in part by Japan Society for the Promotion of Science (JSPS) KAKENHI Grant Number 15K21765, JP18H04430 in Middle Molecular Strategy, JP15K05440, and JP18K05134, by the Swiss National Science Foundation, by the Swiss Nanoscience Institute, by COST action MP1303 “Understanding and Controlling nano and Mesoscale Friction”, and by the Okayama Prefecture Industrial Promotion Foundation and Grant for Promotion of OUS Research Projects. O.K. and A.S.F. have been supported by the Academy of Finland through its Centres of Excellence Program Project No. 915804, and by the World Premier International Research Center Initiative (WPI), MEXT, Japan. They acknowledge use of the CSC, Helsinki for computational resources. O.K. would like to thank to Aliaksandr V. Yakutovich for his help with the AFM simulations. Funding Information: This work was supported in part by Japan Society for the Promotion of Science (JSPS) KAKENHI Grant Number 15K21765 JP18H04430 in Middle Molecular Strategy, JP15K05440, and JP18K05134 by the Swiss National Science Foundation, by the Swiss Nanoscience Institute, by COST action MP1303 "Understanding and Controlling nano and Mesoscale Friction", and by the Okayama Prefecture Industrial Promotion Foundation and Grant for Promotion of OUS Research Projects. O.K. and A.S.F. have been supported by the Academy of Finland through its Centres of Excellence Program Project No. 915804, and by the World Premier International Research Center Initiative (WPI) MEXT, Japan. They acknowledge use of the CSC, Helsinki for computational resources. O.K. would like to thank to Aliaksandr V. Yakutovich for his help with the AFM simulations. Publisher Copyright: © 2018 American Chemical Society.

PY - 2018/8/28

Y1 - 2018/8/28

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 - Glaser coupling

KW - anthracene

KW - atomic force microscopy

KW - on-surface chemical reaction

KW - trimethylsilyl

UR - http://www.scopus.com/inward/record.url?scp=85052327716&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85052327716&partnerID=8YFLogxK

U2 - 10.1021/acsnano.8b05116

DO - 10.1021/acsnano.8b05116

M3 - Article

C2 - 30086235

AN - SCOPUS:85052327716

SN - 1936-0851

VL - 12

SP - 8791

EP - 8797

JO - ACS nano

JF - ACS nano

IS - 8

ER -

Diacetylene linked anthracene oligomers synthesized by one-shot homocoupling of trimethylsilyl on Cu(111)

Abstract

Bibliographical note

Keywords

Access

OpenUrl availability

Other files and links

Fingerprint

Cite this