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.

Assembly of a Supramolecular Capsule on a Molecular Printboard / Corbellini, F.; Mulder, A.; Sartori, Andrea; Ludden, M. J. W.; Casnati, Alessandro; Ungaro, Rocco; Huskens, J.; CREGO CALAMA, M.; Reinhoudt, D. N.. - In: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY. - ISSN 0002-7863. - 126:(2004), pp. 17050-17058. [10.1021/ja046780j]

Assembly of a Supramolecular Capsule on a Molecular Printboard

SARTORI, Andrea;CASNATI, Alessandro;UNGARO, Rocco;
2004-01-01

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.
2004
Assembly of a Supramolecular Capsule on a Molecular Printboard / Corbellini, F.; Mulder, A.; Sartori, Andrea; Ludden, M. J. W.; Casnati, Alessandro; Ungaro, Rocco; Huskens, J.; CREGO CALAMA, M.; Reinhoudt, D. N.. - In: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY. - ISSN 0002-7863. - 126:(2004), pp. 17050-17058. [10.1021/ja046780j]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11381/1440956
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