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

Research output: Contribution to journalArticlepeer-review

12 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 languageEnglish (US)
Pages (from-to)8791-8797
Number of pages7
JournalACS nano
Volume12
Issue number8
DOIs
StatePublished - 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

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