Assembly of a supramolecular capsule on a molecular printboard


Corbellini, Francesca and Mulder, Alart and Sartori, Andrea and Ludden, Manon J.W. and Casnati, Alessandro and Ungaro, Rocco and Huskens, Jurriaan and Crego Calama, Mercedes and Reinhoudt, David N. (2004) Assembly of a supramolecular capsule on a molecular printboard. Journal of the American Chemical Society, 126 (51). pp. 17050-17058. ISSN 0002-7863

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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.
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Copyright:© 2004 American Chemical Society
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Metis ID: 222261