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Título: | Self-association of a naphthalene-capped-β-cyclodextrin through cooperative strong hydrophobic interactions |
Autor: | González-Álvarez, M. José; Méndez-Ardoy, Alejandro CSIC ORCID; Benito, Juan M. CSIC ORCID CVN ; García Fernández, José Manuel CSIC ORCID; Mendicuti, Francisco | Fecha de publicación: | 2011 | Editor: | Elsevier | Citación: | Journal of Photochemistry and Photobiology A: Chemistry 223: 25- 36 (2011) | Resumen: | NMR, circular dichroism and fluorescence techniques were used to study the structure in solution of a new β-cyclodextrin derivate in which naphthalene chromophore group is bridged to O(2) and O(3) secondary positions of the same glucopyranose unit through a bidentate hinge. The results point to the formation of a very stable dimer in aqueous solution which dissociates in non-polar solvents. Dimerization was enthalpy and entropy favoured. The hydrophobic character of the naphthyl moiety plays a very important role in the entropy change sign. Molecular mechanics as well as molecular dynamics calculations indicated that the most stable dimers are head-to-head oriented. For these dimer structures the naphthyl moieties, relatively shielded from the solvent, are sufficiently close to each other to couple their transition moments, but without forming excimers. © 2011 Elsevier B.V. All rights reserved. | URI: | http://hdl.handle.net/10261/75212 | DOI: | 10.1016/j.jphotochem.2011.07.013 | Identificadores: | doi: 10.1016/j.jphotochem.2011.07.013 issn: 1010-6030 |
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