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Spectroscopic elucidation of the interaction of native cyclodextrins and their acetylated derivatives with asymmetric monomethyne cyanine dye

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Abstract

Five novel complexes of asymmetric monomethyne cyanine dye (1), with α-, β-, γ-cyclodextrins and the corresponding functionalized derivatives, namely acetyl-β-(Ac-β-CD) and acetyl-γ-(Ac-γ-CD) cyclodextrins were studied by means of UV–VIS, linear-polarized infrared and fluorescence spectroscopy, as well as scanning electron microscopy, powder X-ray diffraction, and thermal methods both in solution and in solid-state. Computational chemistry methods were employed with the purpose of elucidating the electronic structure and vibrational properties of the organic dye.

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References

  1. Szejtli, J., Osa, T. (eds.): Comprehensive Supramolecular Chemistry, vol. 3, Pergamon Press, Oxford (1996)

  2. Saenger, W., Atwood, J.L., Davies, J.E.D., MacNicol, D.D. (eds): Structural Aspects of Cyclodextrins and their Inclusion Complexes. In Inclusion Compounds, vol. 2, pp. 231–259. Academic Press, New York (1984)

  3. Bender, M., Komiyama, K.: Cyclodextrin Chemistry, chapter 3. Springer-Verlag, New York (1978)

    Book  Google Scholar 

  4. Szejtli, J.: Introduction and general overview of cyclodextrin chemistry. Chem. Rev. 98, 1743–1754 (1998)

    Article  CAS  Google Scholar 

  5. Rekharsky, M., Inoue, Y.: Complexation thermodynamics of cyclodextrins. Chem. Rev. 98, 1875–1918 (1998)

    Article  CAS  Google Scholar 

  6. Connors, K.A.: The stability of cyclodextrin complexes in solution. Chem. Rev. 97, 1325–1358 (1997)

    Article  CAS  Google Scholar 

  7. Hapiot, F., Tilloy, S., Monflier, E.: Cyclodextrins as supramolecular hosts for organometallic complexes. Chem. Rev. 106, 767–782 (2006)

    Article  CAS  Google Scholar 

  8. Dodziuk, H. (ed.): Cyclodextrins and Their Complexes. Chemistry, Analytical Methods, Applications. Wiley-VCH Verlag GmbH&Co. KGaA, Weinheim (2006)

    Google Scholar 

  9. Wenz, G., Han, B., Muller, A.: Cyclodextrin rotaxanes and polyrotaxanes. Chem. Rev. 106, 782–817 (2006)

    Article  CAS  Google Scholar 

  10. Harada, A., Li, J., Kamachi, M.: Synthesis of a tubular polymer from threaded cyclodextrins. Nature 364, 516–518 (1993)

    Article  CAS  Google Scholar 

  11. Li, G., McGown, L.: Molecular nanotube aggregates of β- and γ-cyclodextrins linked by diphenylhexatrienes. Science 264, 249–251 (1994)

    Article  CAS  Google Scholar 

  12. Kaliappan, R., Maddipatla, M.M., Kaanumalle, L., Ramamurthy, V.: Crystal engineering principles applied to solution photochemistry: controlling the photodimerization of stilbazolium salts within γ-cyclodextrin and cucurbit[8]uril in water. Photochem. Photobiol. Sci. 6, 737–741 (2007)

    Article  CAS  Google Scholar 

  13. Ivanova, B., Simeonov, V., Arnaudov, M., Tsalev, D.: Linear-dichroic infrared spectroscopy-validation and experimental design of the new orientation technique of solid samples as suspension in nematic liquid crystal. Spectrochim. Acta A 67, 66–75 (2007)

    Article  CAS  Google Scholar 

  14. Ivanova, B., Spiteller, M.: Organic mandelates as promising materials with non-linear optical application, Struct. chem. (2010). doi:10.1007/s11224-010-9635-5

  15. Ivanova, B., Spiteller, M.: On the conformations and properties of the l-tryptophyl-containing peptides in solution, depending of the pH–theoretical study vs. experiments. Biopolymers 93, 727–734 (2010)

    CAS  Google Scholar 

  16. Ivanova, B., Spiteller, M.: Noncentrosymmetric crystals with marked nonlinear optical properties. J. Phys. Chem. A 114, 5099–5103 (2010)

    Article  CAS  Google Scholar 

  17. Ivanova, B., Spiteller, M.: On the application of the organic barbiturates as NLO materials. Cryst. Growth Des. 10, 2470–2474 (2010)

    Article  CAS  Google Scholar 

  18. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Zakrzewski, V.G., Montgomery Jr, J.A., Stratmann, R.E., Burant, J.C., Dapprich, S., Millam, J.M., Daniels, A.D., Kudin, K.N., Strain, M.C., Farkas, Ö., Tomasi, J., Barone, V., Cossi, M., Cammi, R., Mennucci, B., Pomelli, C., Adamo, C., Clifford, S., Ochterski, J., Petersson, G.A., Ayala, P.Y., Cui, Q., Morokuma, K., Salvador, P., Dannenberg, J.J., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Cioslowski, J., Ortiz, J.V., Baboul, A.G., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komáromi, I., Gomperts, R., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nanayakkara, A., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M., Andres, L., Gonzalez, C., Head-Gordon, M., Replogle, E.S., Pople, J.A.: Gaussian 98. Gaussian, Inc., Pittsburgh (1998)

    Google Scholar 

  19. “DALTON”, a molecular electronic structure program, Release 2.0. http://www.kjemi.uio.no/software/dalton/dalton.html (2005)

  20. Zhurko, G.A., Zhurko, D.A.: ChemCraft: Tool for treatment of chemical data, Version build 08 (2005)

  21. Deligeorgiev, T., Zaneva, D., Katerinopoulos, H., Kolev, V.: A novel method for the preparation of monomethine cyanine dyes. Dyes Pigments 41, 49–54 (1999)

    Article  CAS  Google Scholar 

  22. Benesi, H.A., Hildebrand, J.H.: A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. J. Am. Chem. Soc. 71, 2703–2707 (1949)

    Article  CAS  Google Scholar 

  23. Petinova, A., Metsov, S., Petkov, I., Stoyanov, S.: Photophysical behaviours of some 2-styrylindolium dyes in aqueos solutions and in the presence of cyclodextrins. J. Incl. Phenom. Macrocycl. Chem. 59, 183–190 (2007)

    Article  CAS  Google Scholar 

  24. Inigo, X., Garcıa-Zubiri, G., Gonzalez-Gaitano, G., Sanchez, M., Ramon-Isasi, J.: FTIR study of dibenzofuran-2-carboxylic acid and its complexes with β-cyclodextrin. Vib. Spectrosc. 33, 205–213 (2003)

    Article  Google Scholar 

  25. Gaviraa, J.M., Hernanza, A., Bratu, I.: Dehydration of β-cyclodextrin: an IR ν(OH) band profile analysis. Vib. Spectrosc. 32, 137–146 (2003)

    Article  Google Scholar 

  26. de Sousa, F.B., Oliveira, M.F., Lula, I.S., Sansiviero, M., Cortes, M., Sinisterra, R.: Study of inclusion compound in solution involving tetracycline and β-cyclodextrin by FTIR-ATR. Vib. Spectrosc. 46, 57–62 (2008)

    Article  Google Scholar 

  27. Cannava, C., Crupi, V., Ficarra, P., Guardo, M., Majolino, D., Stancanelli, R., Venuti, V.: Physicochemical characterization of coumestrol/β-cyclodextrins inclusion complexes by UV–vis and FTIR-ATR spectroscopies. Vib. Spectrosc. 48, 172–178 ((2008))

    Article  Google Scholar 

  28. Roy, D., Deb, N., Ghosh, B., Mukherjee, A.: Inclusion of riboflavin in beta-cyclodextrin: a fluorimetric and absorption spectrometric study. Spectrochim. Acta A 73, 201–204 (2009)

    Article  Google Scholar 

  29. Hao, X., Li, N., Luo, H.: Determination of dextran sulfate sodium with crystal violet by triple-wavelength overlapping resonance Rayleigh scattering. Spectrochim. Acta A 71, 1673–1677 (2009)

    Article  Google Scholar 

  30. Zhang, M., Li, J., Zhanga, L., Chao, J.: Preparation and spectral investigation of inclusion complex of caffeic acid with hydroxypropyl-β-cyclodextrin. Spectrochim. Acta A 71, 1891–1895 (2009)

    Article  Google Scholar 

  31. Harata, K.: Structural aspects of stereodifferentiation in the solid state. Chem. Rev. 98, 1803–1828 (1998)

    Article  CAS  Google Scholar 

  32. Lindner, K., Saenger, W.: Crystal and molecular structure of cyclohepta-amylose dodecahydrate. Carbohydr. Res. 99, 103–115 (1982)

    Article  CAS  Google Scholar 

  33. Saenger, W., Jacob, J., Gessler, K., Steiner, T., Hoffman, D., Sanbe, H., Koizumi, K., Smoth, S., Kakaha, T.: Structures of the common cyclodextrins and their larger analogues-beyond the doughnut. Chem. Rev. 98, 1787–1802 (1998)

    Article  CAS  Google Scholar 

  34. Kolev, T., Koleva, B.B., Seidel, R.W., Spiteller, M., Sheldrick, W.S.: New aspects on the origin of color in the solid state. Coherently shifting of the protons in violurate crystals. Cryst. Growth Des. 9, 3348–3352 (2009)

    Article  CAS  Google Scholar 

  35. Kolev, T., Tsanev, T., Kotov, S., Mayer-Figge, H., Spiteller, M., Sheldrick, W.S., Koleva, B.: Anyles of 4-benzoylpyridine-crystal structure and spectroscopic properties. Dyes Pigments 82, 95–101 (2009)

    Article  CAS  Google Scholar 

  36. Koleva, B.B., Kolev, T., Seidel, R., Spiteller, M., Mayer-Figge, H., Sheldrick, W.: Self-assembly of hydrogensquarates: crystal structures and properties. J. Phys. Chem. A 113, 3088–3095 (2009)

    Article  CAS  Google Scholar 

  37. Koleva, B.B., Kolev, T., Seidel, R.W., Mayer-Figge, H., Spiteller, M., Sheldrick, W.S.: On the origin of the color in the solid state. Crystal structure and optical and magnetic properties of 4-cyanopyridinium hydrogensquarate monohydrate. J. Phys. Chem. A 112, 2899–2905 (2008)

    Article  CAS  Google Scholar 

  38. Ivanova, B., Nikolova, R., Lamshöft, M., Tsanova, P., Petkov, I., Ivanov, P., Spiteller, M.: Surface interaction and self-assembly of cyclodextrins with organic dyes. J. Incl. Phenom. Macrocycl. Chem. 67, 317–324 (2010)

    Article  CAS  Google Scholar 

  39. Giordano, F., Novak, C., Moyano, J.: Thermal analysis of cyclodextrins and their inclusion compounds. Thermochim. Acta 380, 123–151 (2001)

    Article  CAS  Google Scholar 

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Acknowledgments

The authors wish to thank Prof. T. Deligeorgiev for the guide-lines about the synthesis of the dye, as well as Prof. B. Ivanova for the quantum chemical calculations and helpful discussions. I.P. thanks the National Science Fund of Bulgarian Ministry of Education and Science, project DTK 02-25/2009.

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

    E. Kostadinova, S. Kaloyanova, St. Stoyanov & I. Petkov

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  1. E. Kostadinova
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  2. S. Kaloyanova
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Correspondence to I. Petkov.

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Kostadinova, E., Kaloyanova, S., Stoyanov, S. et al. Spectroscopic elucidation of the interaction of native cyclodextrins and their acetylated derivatives with asymmetric monomethyne cyanine dye. J Incl Phenom Macrocycl Chem 72, 63–69 (2012). https://doi.org/10.1007/s10847-011-9939-0

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