6533b838fe1ef96bd12a3dff

RESEARCH PRODUCT

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

Adam S. FosterAdam S. FosterAdam S. FosterRémy PawlakOndrěj KrejčíLifen PengShigeki KawaiErnst MeyerFeng XuAkihiro Orita

subject

Materials scienceTrimethylsilylta221General Physics and Astronomy02 engineering and technology010402 general chemistryPhotochemistry01 natural sciencesChemical reactionchemistry.chemical_compoundAdsorptionMoleculeGeneral Materials Scienceon-surface chemical reactionAnthraceneatomic force microscopyDiacetyleneanthraceneGlaser couplingGeneral Engineeringtrimethylsilyl021001 nanoscience & nanotechnologyTriple bond0104 chemical sciencesMonomerchemistry0210 nano-technology

description

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. Peer reviewed

https://doi.org/10.1021/acsnano.8b05116