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Surface interaction and self-assembly of cyclodextrins with organic dyes

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Abstract

The interaction of seven novel substituted merocyanine dyes, i.e. 1-methyl-4-[2-(3-methoxy-4-hydroxyphenyl)ethenyl)]pyridinium iodide, 1-methyl-4-[2-(3,5-dimethoxy-4-hydroxyphenyl)ethenyl)]pyridinium iodide, 1-methyl-4-[2-(4-dimethylaminophenyl)ethenyl)]pyridinium iodide, their quinoide forms as well as 1-methyl-4-[2-(3-methoxy-4-oxocyclohexadienilydene)ethylidene]-1,4-dihydropyridine, 1-methyl-4-[2-(3,5-dimethoxy-4-oxocyclohexadienilydene)ethylidene]-1,4-dihydropyridine, with α-CD, γ-CD as well as functionalized γ-cyclodextrin phosphate sodium salt is studied by the methods such as UV–Vis and fluorescence spectroscopy, linear-polarized infrared (IR-LD) spectroscopy of oriented colloids in nematic host, 1H- and 13C-NMR spectroscopy, HPLC ESI tandem mass spectrometry, scanning electron and tunneling microscopy, powder X-ray diffraction as well as thermal methods. A formation of the 1D and 2D “supramolecular polymers” with nanosizes is found. The dyes are adsorbed on the CDs surface and form a hexagonal microcrystalline sub-structures. Remarkable fluorescence properties depending of the type of the substituent in the dyes, in solid-state are observed.

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Acknowledgements

B.K. wishes to thank the Alexander von Humboldt Foundation for the Fellowship. M.S. and B.K. wishes to thank the DAAD for a grant within the priority program “Stability Pact South-Eastern Europe”. M.S. thanks the DFG grand SP 255/21-1. P.I., B.K. and R.N. thanks the National Research Fund of Bulgaria (TK01/0167 and DO-02-82/2008-UNION)

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Authors and Affiliations

  1. Institut für Umweltforschung, Universität Dortmund, Otto-Hahn-Strasse 6, 44221, Dortmund, Germany

    Bojidarka Ivanova, Marc Lamshöft & Michael Spiteller

  2. Faculty of Chemistry, Sofia University St. Kl. Ohridski, 1, J. Bourchier Blvd, 1164, Sofia, Bulgaria

    Rositca Nikolova, Penka Tsanova & Ivan Petkov

  3. Institute of Organic Chemistry, BAS, Acad. G. Bonchev, Str. bloc 9, 1113, Sofia, Bulgaria

    Petko Ivanov

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  1. Bojidarka Ivanova
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  2. Rositca Nikolova
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  3. Marc Lamshöft
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  4. Penka Tsanova
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  5. Ivan Petkov
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  6. Petko Ivanov
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Correspondence to Bojidarka Ivanova.

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Ivanova, B., Nikolova, R., Lamshöft, M. et al. Surface interaction and self-assembly of cyclodextrins with organic dyes. J Incl Phenom Macrocycl Chem 67, 317–324 (2010). https://doi.org/10.1007/s10847-009-9712-9

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  • DOI: https://doi.org/10.1007/s10847-009-9712-9

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