AVS 58th Annual International Symposium and Exhibition
    Surface Science Division Monday Sessions
       Session SS1-MoA

Invited Paper SS1-MoA1
Observation and Modeling of Chiral Modifier-Substrate Complexes on Pt(111)

Monday, October 31, 2011, 2:00 pm, Room 109

Session: Selectivity and Reactivity of Chemisorbed Species
Presenter: Bjoerk Hammer, Aarhus University, Denmark
Authors: B. Hammer, Aarhus University, Denmark
V. Demers-Carpentier, Université Laval, Quebec, Canada
P.H. McBreen, Université Laval, Quebec, Canada
Correspondent: Click to Email
We present a combined density functional theory (DFT) and scanning tunneling microscopy (STM) study of the complex formation between the chiral modifier naphthylethylamine (NEA) and the model substrate trifluoroacetophenone (TFAP) on a Pt(111) surface. The two molecules interact via a hydrogen bond between the amine group on the NEA and the carbonyl on the TFAP. Many different realization of the hydrogen bond exist depending on the relative position and orientation of the two molecules. However, only very few are observed experimentally. These are all among the most stable structures found in DFT. The chemisorbed TFAP is prochiral and hydrogenation of the carbonyl would lead to a chiral product. The prochirality of TFAP when forming a complex with NEA is regiospecific, i.e., it depends on the position at which the TFAP is chemisorbed relative to the NEA. The origin of this regiospecificity is discussed.