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

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

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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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 language	English
Pages (from-to)	269-274
Journal	European journal of organic chemistry
Volume	2000
Issue number	2
DOIs	https://doi.org/10.1002/(SICI)1099-0690(200001)2000:2<269::AID-EJOC269>3.0.CO;2-F
Publication status	Published - 2000

Keywords

Cavitands
Cage compounds
Calixarenes
Gold
Interfaces
Monolayers
Carcerands

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

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title = "Synthesis of (hemi)carceplex adsorbates for self-assembly on gold",

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.",

keywords = "Cavitands, Cage compounds, Calixarenes, Gold, Interfaces, Monolayers, Carcerands",

author = "Bart-Hendrik Huisman and Rudkevich, {Dmitry M.} and Angeles Farran and Willem Verboom and {van Veggel}, {Frank C.J.M.} and Reinhoudt, {David N.}",

year = "2000",

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

language = "English",

volume = "2000",

pages = "269--274",

journal = "European journal of organic chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH Verlag",

number = "2",

}

TY - JOUR

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

AU - Huisman, Bart-Hendrik

AU - Rudkevich, Dmitry M.

AU - Farran, Angeles

AU - Verboom, Willem

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

AU - Reinhoudt, David N.

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 - Cavitands

KW - Cage compounds

KW - Calixarenes

KW - Gold

KW - Interfaces

KW - Monolayers

KW - Carcerands

U2 - 10.1002/(SICI)1099-0690(200001)2000:2<269::AID-EJOC269>3.0.CO;2-F

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

M3 - Article

SN - 1434-193X

VL - 2000

SP - 269

EP - 274

JO - European journal of organic chemistry

JF - European journal of organic chemistry

IS - 2

ER -

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

Abstract

Keywords

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