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Synthesis 1995; 1995(8): 989-997
DOI: 10.1055/s-1995-4021
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Synthesis of Self-Assembling Resorcin[4]arene Tetrasulfide Adsorbates

Eggo U. Thoden van Velzen, Johan F.J. Engbersen, David N. Reinhoudt*
  • *Department of Organic Chemistry, MESA-Research Institute, University of Twente, P.O. Box 217, 7500 AE Enschede, The Netherlands, E-mail ORGCHEM@C.T.UTWENTE.NL
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Publication Date:
31 December 2000 (online)

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The synthesis of a new type of host adsorbate possessing a large resorcin[4]arene headgroup and four di-n-decyl sulfide chains underneath is described. The cross-sectional area of the alkyl chains is equal or larger than that of the headgroups which makes these resorcin[4]arene tetrasulfides suitable for self-assembly onto gold surfaces to form well-packed monolayers of which the outer interface is composed of receptor sites and the alkyl chains underneath the cavity headgroups passivate the gold surface. Resorcin[4]arene tetrasulfides with the following functionalities at the resorcin[4]arene headgroup were synthesized: methylene ether (the so-called cavitand), methyl ether, 2-fluoroethyl, several carboxyl esters, N-propylacetamide and hydroxy.

New receptor adsorbates for self-assembling monolayers are described.