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

B.H. Huisman, D.M. Rudkevich, Dmitry M. Rudkevich, Angeles Farran, A. Farran, Willem Verboom, F.C.J.M. van Veggel, David Reinhoudt

Research output: Contribution to journalArticleAcademicpeer-review

12 Citations (Scopus)

Abstract

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 languageUndefined
Pages (from-to)269-274
JournalEuropean journal of organic chemistry
Volume2000
Issue number2
DOIs
Publication statusPublished - 2000

Keywords

  • METIS-106268
  • Cavitands
  • Cage compounds
  • Calixarenes
  • Gold
  • Interfaces
  • Monolayers
  • IR-11648
  • Carcerands

Cite this

Huisman, B.H. ; Rudkevich, D.M. ; Rudkevich, Dmitry M. ; Farran, Angeles ; Farran, A. ; Verboom, Willem ; van Veggel, F.C.J.M. ; Reinhoudt, David. / Synthesis of (hemi)carceplex adsorbates for self-assembly on gold. In: European journal of organic chemistry. 2000 ; Vol. 2000, No. 2. pp. 269-274.
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abstract = "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.",
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Synthesis of (hemi)carceplex adsorbates for self-assembly on gold. / Huisman, B.H.; Rudkevich, D.M.; Rudkevich, Dmitry M.; Farran, Angeles; Farran, A.; Verboom, Willem; van Veggel, F.C.J.M.; Reinhoudt, David.

In: European journal of organic chemistry, Vol. 2000, No. 2, 2000, p. 269-274.

Research output: Contribution to journalArticleAcademicpeer-review

TY - JOUR

T1 - Synthesis of (hemi)carceplex adsorbates for self-assembly on gold

AU - Huisman, B.H.

AU - Rudkevich, D.M.

AU - Rudkevich, Dmitry M.

AU - Farran, Angeles

AU - Farran, A.

AU - Verboom, Willem

AU - van Veggel, F.C.J.M.

AU - Reinhoudt, David

PY - 2000

Y1 - 2000

N2 - 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.

AB - 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.

KW - METIS-106268

KW - Cavitands

KW - Cage compounds

KW - Calixarenes

KW - Gold

KW - Interfaces

KW - Monolayers

KW - IR-11648

KW - Carcerands

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DO - 10.1002/(SICI)1099-0690(200001)2000:2<269::AID-EJOC269>3.0.CO;2-F

M3 - Article

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SP - 269

EP - 274

JO - European journal of organic chemistry

JF - European journal of organic chemistry

SN - 1434-193X

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