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

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

Research output: Chapter in Book/Report/Conference proceedingChapterAcademicpeer-review

20 Downloads (Pure)


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
Number of pages19
ISBN (Electronic)978-1-4020-5022-0
ISBN (Print)978-1-4020-5021-3, 978-90-481-7258-0
Publication statusPublished - 2007


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


Dive into the research topics of 'Calixarenes on molecular printboards multivalent binding, capsule formation, and surface patterning'. Together they form a unique fingerprint.

Cite this