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 journalArticle

4 Citations (Scopus)

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

Fingerprint

Anthracene
anthracene
oligomers
Oligomers
shot
Oligomerization
Force measurement
Silicon
Adsorbates
Density functional theory
Copper
Chemical reactions
Atomic force microscopy
Nanostructures
chemical reactions
monomers
Monomers
fragments
atomic force microscopy
Annealing

Keywords

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

Cite this

Diacetylene linked anthracene oligomers synthesized by one-shot homocoupling of trimethylsilyl on Cu(111). / Kawai, Shigeki; Krejčí, Ondrěj; Foster, Adam S.; Pawlak, Rémy; Xu, Feng; Peng, Lifen; Orita, Akihiro; Meyer, Ernst.

In: ACS nano, Vol. 12, No. 8, 28.08.2018, p. 8791-8797.

Research output: Contribution to journalArticle

Kawai, S, Krejčí, O, Foster, AS, Pawlak, R, Xu, F, Peng, L, Orita, A & Meyer, E 2018, 'Diacetylene linked anthracene oligomers synthesized by one-shot homocoupling of trimethylsilyl on Cu(111)', ACS nano, vol. 12, no. 8, pp. 8791-8797. https://doi.org/10.1021/acsnano.8b05116
Kawai, Shigeki ; Krejčí, Ondrěj ; Foster, Adam S. ; 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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AU - Pawlak, Rémy

AU - Xu, Feng

AU - Peng, Lifen

AU - Orita, Akihiro

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