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Self-association of a naphthalene-capped-β-cyclodextrin through cooperative strong hydrophobic interactions

Paper ID Volume ID Publish Year Pages File Format Full-Text
27416 44021 2011 12 PDF Available
Title
Self-association of a naphthalene-capped-β-cyclodextrin through cooperative strong hydrophobic interactions
Abstract

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.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► 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.

Keywords
Cyclodextrins; Fluorescence; Circular dichroism; Molecular modelling; Hydrophobic effect
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Self-association of a naphthalene-capped-β-cyclodextrin through cooperative strong hydrophobic interactions
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 223, Issue 1, 5 September 2011, Pages 25–36
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
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