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Diels–Alder attachment of a planar organic molecule to a dangling bond dimer on a hydrogenated semiconductor surface

(2016) PHYSICAL CHEMISTRY CHEMICAL PHYSICS. 18(25). p.16757-16765
Author
Organization
Abstract
Construction of single-molecule electronic devices requires the controlled manipulation of organic molecules and their properties. This could be achieved by tuning the interaction between the molecule and individual atoms by local "on-surface'' chemistry, i.e., the controlled formation of chemical bonds between the species. We demonstrate here the reversible attachment of a planar conjugated polyaromatic molecule to a pair of unpassivated dangling bonds on a hydrogenated Ge(001): H surface via a Diels-Alder [4+2] addition using the tip of a scanning tunneling microscope (STM). Due to the small stability difference between the covalently bonded and a nearly undistorted structure attached to the dangling bond dimer by long-range dispersive forces, we show that at cryogenic temperatures the molecule can be switched between both configurations. The reversibility of this covalent bond forming reaction may be applied in the construction of complex circuits containing organic molecules with tunable properties.
Keywords
SCANNING TUNNELING MICROSCOPE, ATOMIC-SCALE, ELECTRON-TRANSPORT, SINGLE, STM, SIMULATION, JUNCTIONS, SPECTROSCOPY, MANIPULATION, REACTIVITY

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Citation

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MLA
Godlewski, Szymon, et al. “Diels–Alder Attachment of a Planar Organic Molecule to a Dangling Bond Dimer on a Hydrogenated Semiconductor Surface.” PHYSICAL CHEMISTRY CHEMICAL PHYSICS, vol. 18, no. 25, Royal Society of Chemistry (RSC), 2016, pp. 16757–65, doi:10.1039/c6cp02346k.
APA
Godlewski, S., Kawai, H., Engelund, M., Kolmer, M., Zuzak, R., Garcia-Lekue, A., … Saeys, M. (2016). Diels–Alder attachment of a planar organic molecule to a dangling bond dimer on a hydrogenated semiconductor surface. PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 18(25), 16757–16765. https://doi.org/10.1039/c6cp02346k
Chicago author-date
Godlewski, Szymon, Hiroyo Kawai, Mads Engelund, Marek Kolmer, Rafal Zuzak, Aran Garcia-Lekue, Gerard Novell-Leruth, et al. 2016. “Diels–Alder Attachment of a Planar Organic Molecule to a Dangling Bond Dimer on a Hydrogenated Semiconductor Surface.” PHYSICAL CHEMISTRY CHEMICAL PHYSICS 18 (25): 16757–65. https://doi.org/10.1039/c6cp02346k.
Chicago author-date (all authors)
Godlewski, Szymon, Hiroyo Kawai, Mads Engelund, Marek Kolmer, Rafal Zuzak, Aran Garcia-Lekue, Gerard Novell-Leruth, Antonio M Echavarren, Daniel Sanchez-Portal, Christian Joachim, and Mark Saeys. 2016. “Diels–Alder Attachment of a Planar Organic Molecule to a Dangling Bond Dimer on a Hydrogenated Semiconductor Surface.” PHYSICAL CHEMISTRY CHEMICAL PHYSICS 18 (25): 16757–16765. doi:10.1039/c6cp02346k.
Vancouver
1.
Godlewski S, Kawai H, Engelund M, Kolmer M, Zuzak R, Garcia-Lekue A, et al. Diels–Alder attachment of a planar organic molecule to a dangling bond dimer on a hydrogenated semiconductor surface. PHYSICAL CHEMISTRY CHEMICAL PHYSICS. 2016;18(25):16757–65.
IEEE
[1]
S. Godlewski et al., “Diels–Alder attachment of a planar organic molecule to a dangling bond dimer on a hydrogenated semiconductor surface,” PHYSICAL CHEMISTRY CHEMICAL PHYSICS, vol. 18, no. 25, pp. 16757–16765, 2016.
@article{8507475,
  abstract     = {{Construction of single-molecule electronic devices requires the controlled manipulation of organic molecules and their properties. This could be achieved by tuning the interaction between the molecule and individual atoms by local "on-surface'' chemistry, i.e., the controlled formation of chemical bonds between the species. We demonstrate here the reversible attachment of a planar conjugated polyaromatic molecule to a pair of unpassivated dangling bonds on a hydrogenated Ge(001): H surface via a Diels-Alder [4+2] addition using the tip of a scanning tunneling microscope (STM). Due to the small stability difference between the covalently bonded and a nearly undistorted structure attached to the dangling bond dimer by long-range dispersive forces, we show that at cryogenic temperatures the molecule can be switched between both configurations. The reversibility of this covalent bond forming reaction may be applied in the construction of complex circuits containing organic molecules with tunable properties.}},
  author       = {{Godlewski, Szymon and Kawai, Hiroyo and Engelund, Mads and Kolmer, Marek and Zuzak, Rafal and Garcia-Lekue, Aran and Novell-Leruth, Gerard and Echavarren, Antonio M and Sanchez-Portal, Daniel and Joachim, Christian and Saeys, Mark}},
  issn         = {{1463-9076}},
  journal      = {{PHYSICAL CHEMISTRY CHEMICAL PHYSICS}},
  keywords     = {{SCANNING TUNNELING MICROSCOPE,ATOMIC-SCALE,ELECTRON-TRANSPORT,SINGLE,STM,SIMULATION,JUNCTIONS,SPECTROSCOPY,MANIPULATION,REACTIVITY}},
  language     = {{eng}},
  number       = {{25}},
  pages        = {{16757--16765}},
  publisher    = {{Royal Society of Chemistry (RSC)}},
  title        = {{Diels–Alder attachment of a planar organic molecule to a dangling bond dimer on a hydrogenated semiconductor surface}},
  url          = {{http://doi.org/10.1039/c6cp02346k}},
  volume       = {{18}},
  year         = {{2016}},
}

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