Novel water-soluble b-cyclodextrin-calix[4]arene couples as fluorescent sensor molecules for the detection of neutral analytes

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Bügler, Jürgen and Engbersen, Johan F.J. and Reinhoudt, David N. (1998) Novel water-soluble b-cyclodextrin-calix[4]arene couples as fluorescent sensor molecules for the detection of neutral analytes. Journal of Organic Chemistry, 63 (16). pp. 5339-5344. ISSN 0022-3263

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Abstract:The synthesis and the host-guest chemistry of two novel fluorescent B-cyclodextrin-calix[4]arene couples 1 and 2 is described. The compounds were prepared by coupling a B-cyclodextrin linked with an aminoxylyl spacer with two different calix[4]arene building blocks each bearing a fluorophore. The fluorophores attached to 1 and 2 are the 2-naphthylamine and the dansyl moiety, respectively. The unsymmetric calix[4]arene functionalization was achieved by monoprotection of the 1,3-diformylcalix[4]arene. The host molecules 1 and 2 were used as fluorescent probes for several organic analytes in aqueous solution. 1 shows sensitivity for a series of neutral organic guest species, such as steroids, terpenes, and other natural products. In contrast, compound 2 does not show sensitivity for organic analytes in aqueous solution. The different behavior of the two fluorescent probes 1 and 2 is explained by the different strength of self-inclusion of each fluorphoric group into the B-cyclodextrin cavity.
Item Type:Article
Copyright:© 1998 American Chemical Society
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Science and Technology (TNW)
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Link to this item:http://purl.utwente.nl/publications/11083
Official URL:http://dx.doi.org/10.1021/jo9723321
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Metis ID: 105985