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Spectral properties of protonated naphthylpyridine in the presence of cyclodexrins

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Abstract

Electronic absorption and fluorescence spectroscopy showed that the addition of 2-hydroxypropyl cyclodextrin derivatives (HP-α-CD, HP-β-CD, and HP-γ-CD) to an aqueous solution of 4-(2-naphthyl)pyridinium perchlorate (2) results in its partial deprotonation and formation of an inclusion complex of 4-(2-naphthyl)pyridine (1) with the cavitand. The stoichiometry and stability of the inclusion complexes of compounds 1 and 2 and 1-methyl-4-(2-naphthyl)-pyridinium perchlorate (3) with cyclodextrins and their hydroxypropyl derivatives (logK = = 1.5–2.7) were studied by 1H NMR titration. Cyclodextrins with the neutral form 1 form more stable complexes than with ionic compounds 2 and 3. The protonation of the nitrogen atom of compound 2 in aqueous solutions can occur in both the ground and excited states, and the fluorescence spectrum exhibits only the band of the protonated form. Quantum chemical simulation of the deprotonation/protonation processes in an aqueous solution of compound 2 in the absence and presence of HP-β-CD was performed. A tendency for shifting the acid-base equilibrium towards the formation of deprotonated form 1 is observed upon the addition of 2-hydroxypropyl cyclodextrin derivatives to the solution.

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References

  1. D. Creed, J. Photochem. Photobiol., 1984, 39, 537.

    Article  CAS  Google Scholar 

  2. A. L. Sobolewski, W. Domcke, J. Phys. Chem. A, 2001, 105, 9275.

    Article  CAS  Google Scholar 

  3. H. Mishra, H. C. Joshi, H. B. Tripathi, S. Maheshwary, N. Sathyamurthy, M. Panda, J. Chandrasekhar, J. Photochem. Photobiol. A: Chem., 2001, 139, 23.

    Article  CAS  Google Scholar 

  4. R. Casadesús, M. Moreno, J. M. Luch, Chem. Phys. Lett., 2002, 356, 423.

    Article  Google Scholar 

  5. Q. Wang, F. Gao, H. Li, S. Zhang, Chin. J. Chem., 2010, 28, 901.

    Article  CAS  Google Scholar 

  6. T. D. Nekipelova, High Energy Chem. (Engl. Transl.), 2010, 44, 290 [Khim. Vys. Energ., 2010, 44, 319].

    Article  CAS  Google Scholar 

  7. V. B. Nazarov, V. G. Avakyan, S. P. Gromov, M. V. Fomina, T. G. Vershinnikova, M. V. Alfimov, Russ. Chem. Bull. (Int. Ed.), 2004, 53, 2525 [Izv. Akad. Nauk, Ser. Khim., 2004, 2420].

    Article  CAS  Google Scholar 

  8. V. B. Nazarov, V. G. Avakian, S. P. Gromov, M. V. Fomina, T. G. Vershinnikova, V. Yu. Rudyak, M. V. Alfimov, Russ. Chem. Bull. (Int. Ed.), 2007, 56, 281 [Izv. Akad. Nauk, Ser. Khim., 2007, 272].

    Article  CAS  Google Scholar 

  9. V. B. Nazarov, V. G. Avakian, S. P. Gromov, A. I. Vedernikov, M. V. Fomina, T. G. Vershinnikova, V. Yu. Gak, N. A. Lobova, V. Yu. Rudyak, M. V. Alfimov, Russ. Chem. Bull. (Int. Ed.), 2010, 59, 941 [Izv. Akad. Nauk, Ser. Khim., 2010, 919].

    Article  CAS  Google Scholar 

  10. S. P. Gromov, V. B. Nazarov, V. G. Avakyan, M. V. Fomina, A. I. Vedernikov, L. G. Kuzmina, T. G. Vershinnikova, N. A. Lobova, V. Yu. Rudyak, M. V. Alfimov, J. A. K. Howard, J. Photochem. Photobiol. A: Chem., 2011, 217, 87.

    Article  CAS  Google Scholar 

  11. S. P. Gromov, M. V. Fomina, Russ. Chem. Bull. (Int. Ed.), 2004, 53, 901 [Izv. Akad. Nauk, Ser. Khim., 2004, 864].

    Article  CAS  Google Scholar 

  12. C. Frassineti, S. Ghelli, P. Gans, A. Sabatini, M. S. Moruzzi, A. Vacca, Anal. Biochem., 1995, 231, 374.

    Article  CAS  Google Scholar 

  13. J. J. P. Stewart, J. Comput. Chem., 1989, 10, 209.

    Article  CAS  Google Scholar 

  14. V. B. Nazarov, V. G. Avakyan, M. V. Alfimov, Ros. nanotekhnologii [Russian Nanotechnologies], 2007, 2, 68 (in Russian).

    Google Scholar 

  15. V. G. Avakyan, V. B. Nazarov, M. V. Alfimov, in Naphthalene. Structure, Properties, and Applications, Eds G. I. Antsyforov, A. F. Ivanski, Nova Science Publishers, Inc., New York, 2012, p. 127.

  16. B. Kallies, R. Mitzner, J. Mol. Model., 1995, 1, 68.

    Article  CAS  Google Scholar 

  17. C. W. Yong, C. Washington, W. Smith, Pharm. Res., 2008, 25, 1092.

    Article  CAS  Google Scholar 

  18. H.-J. Schneider, F. Hacket, V. Rüdiger, H. Ikeda, Chem. Rev., 1998, 98, 1755.

    Article  CAS  Google Scholar 

  19. M. C. Sicilia, A. Nino, C. Munoz-Caro, J. Phys. Chem. A, 2005, 109, 8341.

    Article  CAS  Google Scholar 

  20. F. H. Allen, O. Kennard, R. Taylor, Acc. Chem. Res., 1983, 16, 146.

    Article  CAS  Google Scholar 

  21. J. Van De Streek, Acta Crystallogr., Sect. B, 2006, B62, 567.

    Article  Google Scholar 

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Authors and Affiliations

  1. Institute of Problems of Chemical Physics, Russian Academy of Sciences, 1 prosp. Akad. Semenova, 142432, Chernogolovka, Moscow Region, Russian Federation

    V. B. Nazarov

  2. Photochemistry Center, Russian Academy of Sciences, 7A ul. Novatorov, 119421, Moscow, Russian Federation

    V. G. Avakyan, M. V. Fomina, A. I. Vedernikov, M. V. Alfimov & S. P. Gromov

Authors
  1. V. B. Nazarov
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  2. V. G. Avakyan
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  3. M. V. Fomina
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  4. A. I. Vedernikov
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  5. M. V. Alfimov
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  6. S. P. Gromov
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Correspondence to S. P. Gromov.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2150–2157, October, 2013.

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Nazarov, V.B., Avakyan, V.G., Fomina, M.V. et al. Spectral properties of protonated naphthylpyridine in the presence of cyclodexrins. Russ Chem Bull 62, 2150–2157 (2013). https://doi.org/10.1007/s11172-013-0314-8

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  • DOI: https://doi.org/10.1007/s11172-013-0314-8

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