Scanning Tunneling Microscopy Measurements of the Full Cycle of a Heterogeneous Asymmetric Hydrogenation Reaction on Chirally Modified Pt(111)

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  • Vincent Demers-Carpentier, Université Laval, Canada
  • Guillaume Goubert, Université Laval, Canada
  • Federico Masini, Université Laval, Canada
  • Yi Dong, Université Laval, Canada
  • Anton Michael Havelund Rasmussen
  • Bjørk Hammer
  • Peter H. McBreen, Université Laval, Canada

The hydrogenation of a prochiral substrate, 2,2,2-trifluoroacetophenone (TFAP), on Pt(111) was studied using room-temperature scanning tunneling microscopy (STM) measurements. The experiments were carried out both on a clean surface and on a chirally modified surface, using chemisorbed (R)-(+)-1-(1-naphthyl)ethylamine, ((R)-NEA), as the modifier. On the nonmodified surface, introduction of H2 at a background pressure of ∼1 × 10–6 mbar leads to the rapid break-up of TFAP dimer structures followed by the gradual removal of all TFAP-related images. During the latter step, some monomers display an extra protrusion compared to TFAP in dimer structures. They are attributed to a half-hydrogenated intermediate. The introduction of H2 to a mixture of (R)-NEA and TFAP on Pt(111) leads to the removal of TFAP without any change in the population of the modifier, as required for an efficient chirally modified catalyst.

Original languageEnglish
JournalThe Journal of Physical Chemistry Letters
Pages (from-to)92–96
Publication statusPublished - 2012

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