Abstract
6-Perhydroxyalkylamino-6-perdeoxy-β-cyclodextrins have been synthesised by treating 6-perbromo-6-perdeoxy-cyclodextrins with hydroxyalkylamines. The products (1, 2) are precursors of dendrimeric cyclodextrins in which the cavity provides access for the guest to interact with the branches. A fluorescence study has demonstrated the effects of the branches on binding of anilinonaphthalene sulfonate probes. The hosts show selectivity towards guests, and pH-dependence of binding, consistent with polar interaction between guest sulfonate anions and the protonated amino groups of the dendrimeric structure.
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Tomalia, D.A., Naylor, A.M., Goddard, W.A., Starburst dendrimers: molecular level control of size, shape, surface chemistry, topology and flexibility from atoms to macroscopic matter,Angew. Chem. Int. Ed. Engl.,29, 138–175 (1990)
Ling, C.-C., Darcy, R., 6-S-Hydroxyethylated 6-thiocyclodextrins: expandable host molecules,J. Chem. Soc. Chem. Commun., 203-205 (1993)
Gadelle, A., Defaye, J., Selective halogenation at primary positions of cyclomaltooligosaccharides and a synthesis of per-3,6-anhydro cyclomaltooligosaccharides,Angew Chem. Int. Ed. Engl.,30, 78–80, (1991)
Connors, K.A.,Binding Constants, Wiley, New York, 1987
Catena, G.C., Bright, F.V., Thermodynamic study on the effects of β-cyclodextrin inclusion with anilinonaphthalenesulfonates,Anal. Chem. 61, 905–909 (1989)
Eliseev, A.V., Schneider, H.-J., Molecular recognition of nucleotides, nucleosides and sugars by aminocyclodextrins,J. Am. Chem. Soc.,116, 6081–6088 (1994)
Kosower, E.M., Kanety, H., Intramolecular donor-acceptor systems. 10. Multiple fluorescentes from 8-(phenylamino)-1-naphthalene sulfonates,J. Am. Chem. Soc.,105, 6236–6243 (1983)
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Ahern, C., Darcy, R., O'Keeffe, F. et al. 6-Hydroxyalkylamino-6-deoxy-cyclodextrins: Towards dendrimeric host-molecules. J Incl Phenom Macrocycl Chem 25, 43–46 (1996). https://doi.org/10.1007/BF01041533
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DOI: https://doi.org/10.1007/BF01041533