4.8 Article

Controlling the Position of Functional Groups at the Liquid/Solid Interface: Impact of Molecular Symmetry and Chirality

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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 133, 期 51, 页码 20942-20950

出版社

AMER CHEMICAL SOC
DOI: 10.1021/ja209018u

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资金

  1. European Community [NMP4-SL-2008-214340]
  2. Fund of Scientific Research - Flanders (FWO), K.U.Leuven (GOA)
  3. Belgian Federal Science Policy Office [IAP-6/27]
  4. Institute for the Promotion of Innovation by Science and Technology in Flanders (IWT)
  5. Region Wallonne
  6. FNRS-FRFC
  7. ERA Chemistry/NWO
  8. NWO VICI

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With the aim of controlling the position of functional groups in a substrate-supported monolayer, a new family of functionalized linear alkyl chains was designed and synthesized, aided by molecular mechanics and dynamics simulations of its two-dimensional self-assembly on graphite. The self-assembly of these amino functionalized diamides at the liquid/solid interface was investigated with scanning tunneling microscopy. Intermolecular hydrogen-bonding interactions involving amides, combined with the effect of molecular symmetry and chirality, were found to guide the self-assembly. Control of the relative position and orientation of the amine groups was achieved, in the case of enantiopure compounds. Interestingly, racemates led to both racemic conglomerate and solid solution formation, with a concomitant loss of positional and orientational control of the amino groups as a result.

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