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Chemistry. 2010 Sep 3;16(33):10048-61. doi: 10.1002/chem.200903125.

Fatty acid carboxylate- and anionic surfactant-controlled delivery systems that use mesoporous silica supports.

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  • 1Instituto de Reconocimiento Molecular y Desarrollo Tecnológico, Centro Mixto, Departamento de Química, Universidad Politécnica de Valencia, Camino de Vera s/n. 46022, Valencia, Spain.


We report the preparation of a MCM-41 mesoporous material that contains the dye [Ru(bipy)(3)]Cl(2) (bipy=bipyridine) inside the mesopores and functionalised with suitable binding groups at the entrance of the pores. Solids S1-S3 were obtained by the reaction of the mesoporous material with N-methyl-N'-propyltrimethoxysilylimidazolium chloride, N-phenyl-N'-[3-(trimethoxysilyl)propyl]thiourea, or N-phenyl-N'-[3-(trimethoxysilyl)propyl]urea, respectively. A study of the dye delivery of these systems in buffered water (pH 7.0, 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid (HEPES), 10(-3) mol dm(-3)) in the presence of a family of carboxylate ions was carried out. In the interaction of the anions with the surface of the solids, the response depends on the characteristics of the binding groups (i.e., imidazolium, urea and thiourea) at the pore outlets and their specific interaction with the corresponding anion. The interaction of long-chain carboxylate ions with the binding sites at the surface of the solids resulted in a remarkable inhibition of the delivery of the dye. This inhibition was observed clearly for the dodecanoate anion, whereas the octanoate, decanoate, cholate, deoxycholate, glycodeoxycholate and taurocholate anions induced a certain pore blockage that varied according to the solid studied. The interaction of smaller anions, such as acetate, butanoate, hexanoate and octanoate, with the solids had no effect on the dye release process. The possible use of the gating system for the chromo-fluorogenic detection of anionic surfactants through selective dye delivery inhibition was also explored. Molecular dynamic simulations that use force-field methods have been made to theoretically study the capping carboxylate mechanism. The calculations are in agreement with the experimental results, thus allowing a representation of the dye delivery inhibition in the presence of long-chain carboxylate ions.

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