Assembly of a supramolecular capsule on a molecular printboard

F. Corbellini, A. Mulder, A. Sartori, M.J.W. Ludden, Alessandro Casnati, Rocco Ungaro, Jurriaan Huskens, Mercedes Crego Calama, David Reinhoudt

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Abstract

A molecular capsule based on ionic interactions between two oppositely charged calix[4]arenes, 1 and 2, was assembled both in solution and on a surface. In solution, the formation of the equimolar assembly 1·2 was studied by 1H NMR, ESI-MS, and isothermal titration calorimetry, giving an association constant (Ka) of 7.5 × 105 M-1. A β-cyclodextrin self-assembled monolayer (β-CD SAM) on gold was used as a molecular printboard to anchor the tetraguanidinium calix[4]arene (2). The binding of tetrasulfonate calix[4]arene 1 was monitored by surface plasmon resonance spectroscopy. Rinsing of the surface with a high ionic strength aqueous solution allows the removal of the tetrasulfonate calix[4]arene (1), while by rinsing with 2-propanol it is possible to achieve the complete desorption of the tetraguanidinium calix[4]arene (2) from the β-CD SAM. The Ka for the capsule formation on a surface is 3.5 × 106 M-1, thus comparing well with the Ka determined in solution.
Original languageUndefined
Pages (from-to)17050-17058
Number of pages9
JournalJournal of the American Chemical Society
Volume126
Issue number51
DOIs
Publication statusPublished - 2004

Keywords

  • METIS-222261
  • IR-49632

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