کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
27416 | 44021 | 2011 | 12 صفحه PDF | دانلود رایگان |

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.
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► Dimerization processes, structure and conformational behavior of a new naphthalene-β-cyclodextrin derivate.
► A wide variety of experimental techniques (NMR, UV-absorption, steady-state and lifetime fluorescence and circular dichroism) was used.
► CD derivative self-assemble by strong hydrophobic interactions without the need for inclusion in the neighbor CD.
► Dimerization was enthalpy and entropy favoured.
► Molecular modelling indicated dimers are head-to-head oriented.
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 223, Issue 1, 5 September 2011, Pages 25–36