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Fluorescence Studies of Host–Guest Interaction of a Dansyl Amide Labelled Calix[6]arene

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Abstract

The fluorescence behavior of a calix[6]arene with a dansyl group as fluorescence marker (C6-DA) was investigated with respect to the inclusion properties of alkaloids as atropine and cocaine. A strong hypsochromic shift of the fluorescence band and a strong increase in fluorescence intensity is connected with the interaction of atropine to the lower rim of the C6-DA. The fluorescence increase is saturated at an atropine concentration above the 1:1 complex formation. Addition of cocaine to the complexed atropine-C6-DA leads to a decrease of the fluorescence intensity which could be explained by an exchange mechanism of the complexed molecules. The complexation of the atropine (the “belladonna effect”) is interpreted by electrostatic interaction (proton transfer from the carboxylic group to the nitrogen) with important contribution from hydrogen bonding by the guest OH-group.

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Acknowledgments

This work is supported by the German Federal Ministry of Economy and Labour under grant No. 16IN0217 “ChemoChips.” We thank Dr. M. Friedrich (FSU Jena) for the NMR investigations. Many helpful discussions with Dr. T. Henkel (IPHT Jena) are gratefully acknowledged. Dr. U. Demme (FSU Jena, Institute of Forensic Medicine) was so kind to help us with the cocaine solutions, which we gratefully acknowledge.

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Authors and Affiliations

  1. University of Applied Sciences Jena, Faculty of Medical Engineering, Carl-Zeiss-Promenade, Jena, D-07745, Germany

    K. Schönefeld, R. Ludwig & K.-H. Feller

  2. Freie Universitaet Berlin, Institute of Chemistry, Inorganic and Analytical Chemistry, Fabeckstr. 34–36 D-14195, Berlin, Germany

    R. Ludwig

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  1. K. Schönefeld
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  2. R. Ludwig
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  3. K.-H. Feller
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Correspondence to K.-H. Feller.

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Schönefeld, K., Ludwig, R. & Feller, KH. Fluorescence Studies of Host–Guest Interaction of a Dansyl Amide Labelled Calix[6]arene. J Fluoresc 16, 449–454 (2006). https://doi.org/10.1007/s10895-005-0055-7

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  • DOI: https://doi.org/10.1007/s10895-005-0055-7

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