Synthesis of (hemi)carceplex adsorbates for self-assembly on gold

Bart-Hendrik Huisman, Dmitry M. Rudkevich, Angeles Farran, Willem Verboom, Frank C.J.M. van Veggel, David N. Reinhoudt

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The synthesis of sulfide-functionalized (hemi)carceplexes suitable for self-assembly on gold is described. A noncentrosymmetrical carceplex 9 (guest DMF) was synthesized by the combination of calix[4]arene 4 and resorcin[4]arene 3, while a noncentrosymmetrical hemicarceplex 12 (guest NMP) was prepared by the combination of two different resorcin[4]arenes, 3 and 10. These adsorbates form ordered self-assembled monolayers on gold with their quasi C4v axis perpendicular to the surface. The two positions possible for the incarcerated guest lead to diastereotopic surfaces.
Original languageEnglish
Pages (from-to)269-274
JournalEuropean journal of organic chemistry
Issue number2
Publication statusPublished - 2000


  • Cavitands
  • Cage compounds
  • Calixarenes
  • Gold
  • Interfaces
  • Monolayers
  • Carcerands


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