Tuning Aryl−CH···O Intermolecular Interactions on Pt(111)

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  • Vincent Demers-Carpentier, Canada
  • Marc-André Laliberte
  • ,
  • Yunxiang Pan
  • ,
  • Gautier Mahieu
  • ,
  • Stéphane Lavoie
  • ,
  • Guillaume Goubert
  • ,
  • Bjørk Hammer
  • Peter H. McBreen
Scanning tunneling microscopy (STM) data are reported for the room-temperature adsorption of 2,2,2-trifluoroacetophenone (TFAP), 2,2,2-trifluorovinylbenzene (TFVB), octafluoroacetophenone (OFAP), and methyl benzoate (MB) on Pt(111). The objective of the study is to establish the role of aryl−CH···O bonding in forming self-assembled low-nuclearity structures at room temperature and to compare aryl−CH···O bonding by ester and ketone carbonyl functions. The STM images clearly evidence the formation of homochiral dimers and trimers of TFAP, and density functional theory (DFT) calculations reveal aryl−CH···O bonding as the driving force for dimer formation. In contrast to TFAP, chemisorbed TFVB and OFAP do not form such self-assembled structures as they lack carbonyl and aryl−CH groups, respectively. The self-assembly of MB on Pt(111) differs from that of TFAP, in that it can form structures stabilized by one, as distinct from two, aryl−CH···O bonds. The results are discussed with respect to the enantioselective hydrogenation of α-ketoesters on cinchona modified Pt catalysts.
Original languageEnglish
JournalJournal of Physical Chemistry Part C: Nanomaterials and Interfaces
Volume115
Issue4
Pages (from-to)1355–1360
ISSN1932-7447
DOIs
Publication statusPublished - 13 Dec 2011

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