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Synthesis of Novel b.beta-cyclodextrin Derivatives Bearing a 1-naphthyloxamino-oligo(ethyleneamino) Moiety and their Inclusion Complexation with some Fluorescent Dyes Authors: Yu Liu a; Shi-Zhao Kang a; Li Li a Affiliation: a Department of Chemistry, Nankai University, Tianjin 300071, People's Republic of China. DOI: 10.1080/10610270290029371 Publication Frequency: 8 issues per year Published in: journal Supramolecular Chemistry, Volume 14, Issue 4 2002 , pages 329 - 337 Subject: Organic Chemistry; Number of References: 31 Formats available: PDF (English) Purchase Article: US$32.00 plus VAT - buy now buy now add to cart buy now [ show other buying options ] purchase type customer type online access payment method price Single Article Purchase Personal 3 days credit card US$32.00 plus VAT buy now buy now add to cart add to cart Issue Purchase Any permanent credit card US$397.32 plus VAT buy now buy now add to cart add to cart If you would like to pay in any other currency please see the purchasing help pages for more information. * Sign In Sign In * Online Sample Online Sample Abstract Two novel b.beta-cyclodextrin derivatives bearing a (1-naphthyloxamino)-ethyleneamino ( 4 ) or (1-naphthyloxamino)-diethylenediamino ( 5 ) moiety have been synthesized by a convenient method in 34% and 30% yields, respectively. Examinations of the circular dichroism (CD) spectra and fluorescence lifetime revealed that the naphthyloxamino-oligo (ethyleneamino) moiety tethered to b.beta-cyclodextrin is not deeply embedded in the hydrophobic cavity of b.beta-cyclodextrin itself even in the absence of a guest. The inclusion complexation behavior of 4 and 5 with some fluorescent dyes, i.e. ammonium 8-anilino-1-naphthalenesulfonate (ANS), sodium 2-( p -toluidinyl)naphthalenesulfonate (TNS), Acridine Red (AR) and Rhodamine B (RhB), was assessed in aqueous phosphate buffer solution (pH 7.2) at 25¡ãC by fluorometric titration to give the complex stability constants ( K S ) and Gibbs free energy changes ( b.DeltaG 0 ) for the stoichiometric 1:1 inclusion complexation with the fluorescent dyes. The results obtained indicate that the naphthyloxamino-oligo(ethyleneamino) moiety attached to the b.beta-cyclodextrin ( 1 ) can alter not only the original molecular binding-ability of the parent b.beta-cyclodextrin, but also the molecular selectivity through the micro-environment changes of cyclodextrin cavity, which are discussed from the viewpoints of the size/shape-fit concept and the stereochemical complementary relationship between host cyclodextrin and model substrate. Keywords: Modified Cyclodextrins; Dyes; Inclusion Complexation; Molecular Recognition |

3Â¥2007-06-18 19:15:37
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supramolecular Chemistry 2005 Impact Factor: 1.715 (Thomson ISI Journal Citation Reports 2006) Published By: Taylor & Francis Volume Number: 19 Frequency: 8 issues per year Print ISSN: 1061-0278 Online ISSN: 1029-0478 |

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