Calixarenes on molecular printboards multivalent binding, capsule formation, and surface patterning

Manon J.W. Ludden, Mercedes Crego-Calama, David N. Reinhoudt, Jurriaan Huskens

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Abstract

The divalent binding of bis(adamantyl)-calix[4]arene 4 in solution and at â-cyclodextrin (β-CD) self-assembled monolayers (SAMs) (2) has been investigated. At β-CD SAMs the binding constant is three orders of magnitude higher than the binding constant for the divalent binding of 4 to the β-CD dimer 3 in solution (1.2 x 107 M1). A model that treats the sequential binding events as independent, and takes into account an effective concentration term for the second, intramolecular, binding event explains these results. The buildup and subsequent break-down of a non-covalent capsule consisting of tetra(adamantyl)-calix[4]arene 5 and tetrasulfonate- calix[4]arene 6 at the β-CD SAM was studied by surface plasmon resonance (SPR) spectroscopy. The association constant for capsule formation at β-CD SAMs ((3.5 ± 1.6) x 106 M1) is comparable to the association constant of the capsule in solution ((7.5 ± 1.2) x 10 5 M1). Microcontact printing (μCP) and dip-pen nanolithography (DPN) were applied in the patterning of β-CD SAMs. Stable features were obtained upon printing and writing of the bis(adamantyl)-calix[4] arene 4 at the β-CD SAMs. The features could not be removed upon rinsing with water, while rinsing with 10 mM β-CD resulted in partial removal of the patterns. In contrast features printed at OH-terminated SAMs were removed instantly upon rinsing with water.

Original languageEnglish
Title of host publicationCalixarenes in the Nanoworld
EditorsJacques Vicens, Jack Harrowfield, Lassaad Baklouti
Place of PublicationDordrecht
PublisherSpringer
Pages213-231
Number of pages19
ISBN (Electronic)978-1-4020-5022-0
ISBN (Print)978-1-4020-5021-3, 978-90-481-7258-0
DOIs
Publication statusPublished - 2007

Keywords

  • Cyclodextrins
  • Dip-pen nanolithography
  • Host-guest interactions
  • Microcontact printing
  • Multivalency
  • Non-covalent capsules
  • Self-assembled monolayers
  • Surface patterning
  • 2023 OA procedure

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