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

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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.
Original languageUndefined
Pages (from-to)5339-5344
JournalJournal of organic chemistry
Volume63
Issue number63
DOIs
Publication statusPublished - 1998

Keywords

  • METIS-105985
  • IR-11083

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