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A comparative study on inclusion complexation of substituted anilinonaphthalene sulfonic acids with 1,6,20,25-tetraaza[6.1.6.1]-paracyclophane and β-cyclodextrin

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Abstract

The inclusion complexations of paracyclophane (CP44) and β-cyclodextrin (β-CD) with several anilinonaphthalene sulfonic acids (ANSs) have been characterized via the enhancement of fluorescence spectra upon inclusion. β-CD and CP44 formed 1:1 inclusion complexes with ANSs, and the high stability of inclusion complexes of the latter was demonstrated. The thermodynamic parameters observed from the temperature dependence of the inclusion constants (van’t Hoff analysis) showed that CP44 inclusion complexations with ANSs are enthalpy-driven. Furthermore, the structure of the inclusion complexes was discussed based on 1H- and 2D ROESY-NMR measurements. It was found that CP44 encapsulates the naphthalene moiety of ANSs. On the other hand, differences in the structures of the β-CD inclusion complexes were observed for the 4-OH-substituted ANS. The molecular recognition for the inclusion of β-CD was found to be sensitive compared with that of CP44. In addition, the local polarity inside the CP44 and β-CD cavities was evaluated using ANSs as the fluorescence probe. Based on these results, we have suggested that the local polarity of ANSs in the hydrophobic cavities of CP44 and β-CD plays an important role in quantum yield enhancement upon inclusion.

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References

  1. Bender, M.L., Komiyama, M.: Cyclodextrin chemistry. Springer, New York (1978)

    Book  Google Scholar 

  2. Junquera, E., Penal, C., Aicart, A.: A conductimetric study of the interaction of β-cyclodextrin or hydroxypropyl-β-cyclodextrin with dodecyltrimethylammonium bromide in water solution. Langmuir 11, 4685–4690 (1995)

    Article  CAS  Google Scholar 

  3. Gelb, R.I., Schwartz, L.M., Murray, C.T., Laufer, D.A.: Complexation of 4-biphnyl- carboxylate by cyclohexaamylose. A conductometric and 13C nuclear magnetic resonance spectrometric and analysis. J. Am. Chem. Soc. 100, 3553–3559 (1978)

    Article  CAS  Google Scholar 

  4. Odashima, K., Itai, A., Iitaka, Y., Arata, Y.: Inclusion complex formation in a particular geometry by a water-soluble paracyclophane in aqueous solution. Tetrahedron Lett. 21, 4347–4350 (1980)

    Article  CAS  Google Scholar 

  5. Odashima, K., Koga, K.: Design and syntheses of paracyclophanes having charged side chains that are soluble in neutral aqueous solution. Heterocycles 15, 1151–1154 (1981)

    Article  CAS  Google Scholar 

  6. Berville, M., Karmazin, L., Wytko, J.A., Weiss, J.: Viologen cyclophanes: redox controlled host-guest interactions. Chem. Commun. 51, 15772–15775 (2015)

    Article  CAS  Google Scholar 

  7. Dale, E.J., Vermeulen, N.A., Juricek, M., Barnes, J.C., Young, R.M., Wasielewski, M.R., Stoddart, J.F.: Supramolecular explorations: exhibiting the extent of extended cationic cyclophanes. Acc. Chem. Res. 49, 262–273 (2016)

    Article  CAS  Google Scholar 

  8. Hayashida, O., Kojima, M., Kusano, S.: Biotinylated cyclophane: synthesis, cyclophane-avidin conjugates, and their enhanced guest-binding affinity. J. Org. Chem. 80, 9722–9727 (2015)

    Article  CAS  Google Scholar 

  9. Hayashida, O., Eguchi, C., Kimura, K., Oyama, Y., Nakashima, T., Shioji, K.: Guest binding, cellular uptake, and molecular delivery of water-soluble cyclophanes having a pyrene moiety. Chem. Lett. 39, 1321–1322 (2010)

    Article  CAS  Google Scholar 

  10. Kosower, E.M., Dodiuk, H.: Intramolecular donor-acceptor systems. 3. A third type of emitting singlet state for N-alkyl-6-N-arylamino-2-naphthalenesulfonates. Solvent modulation of substituent effects on charge-transfer emissions. J. Am. Chem. Soc. 100, 4173–4179 (1978)

    Article  CAS  Google Scholar 

  11. Wagner, B.D., Fitzpatrick, S.J.: A comparison of the host-guest inclusion complexes of 1,8-ANS and 2,6-ANS in parent and modified cyclodextrins. J. Incl. Phenom. Macrocycl. Chem. 38, 467–478 (2000)

    Article  CAS  Google Scholar 

  12. Sueishi, Y., Fujita, T., Nakatani, S., Inazumi, N., Osawa, Y.: The enhancement of fluorescence quantum yields of anilinonaphthalene sulfonic acids by inclusion of various cyclodextrins and cucurbit[7]uril. Spectroc. Acta A 114, 344–349 (2013)

    Article  CAS  Google Scholar 

  13. Odashima, K., Itai, A., Iitaka, Y., Koga, K.: Host-guest complex formation between a water-soluble polyparacyclophene and a hydrophobic guest molecule. J. Am. Chem. Soc. 102, 2501–2502 (1980)

    Article  Google Scholar 

  14. Bucherer, H., Stohmann, A.: Aryl-substituted β-naphthylamines and their preparation by the sulphite method. Zeitschrift fuer Farben- und Textil-Chemie 3, 57–62 and 77–81 (1904)

    CAS  Google Scholar 

  15. Velapoldi, R.A., Tonnesen, H.H.: Corrected emission spectra and quantum yields for a series of fluorescent compounds in the visible spectra region. J. Fluoresc. 14, 465–472 (2004)

    Article  CAS  Google Scholar 

  16. Job, P.: Formation and stability of inorganic complexes in solution. Ann. Chim. 9, 113–203 (1928)

    CAS  Google Scholar 

  17. Scott, R.L.: Some comments on the Benesi-Hildebrand equation. Recueil des Travaux Chimiques des Pays-Bas et de la Belgique 75, 787–789 (1956)

    Article  CAS  Google Scholar 

  18. Sueishi, Y., Ohtani, K., Nishimura, N.: The thermal cis-to-trans isomerization of N,N′-diacylindigos. Kinetic pressure, solvent, and substituent effects. Bull. Chem. Soc. Jpn. 58, 810–814 (1985)

    Article  CAS  Google Scholar 

  19. Leffler, J.E.: The interpretation of enthalpy and entropy data. J. Org. Chem. 31, 533–537 (1966)

    Article  CAS  Google Scholar 

  20. Castronuovo, G., Niccoli, M., Varriale, L.: Complexation forces in aqueous solution. Calorimetric studies of the association of 2-hydroxypropyl-β-cyclodextrin with monocarboxylic acids or cycloalkanols. Tetrahedron 63, 7047–7052 (2007)

    Article  CAS  Google Scholar 

  21. Castronuovo, G., Niccoli, M.: Solvent effects on the complexation of 1-alkanols by parent and modified cyclodextrins. Calorimetric studies at 298 K. J. Therm. Anal. Calorim. 103, 641–646 (2011)

    Article  CAS  Google Scholar 

  22. Kosower, E.M., Dodiuk, H., Tanizawa, K., Ottolenghi, M., Orbach, N.: Intramolecular donor-acceptor systems. Radiative and nonradiative processes for the excited states of 2-N-arylamino-6-naphthalenesulfonates. J. Am. Chem. Soc. 97, 2167–2178 (1975)

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama, 700-8530, Japan

    Yoshimi Sueishi, Ayari Itoh & Tadashi Hanaya

  2. Technical Support Division, Graduate School of Science, Osaka University, Toyonaka, Osaka, 560-0043, Japan

    Naoya Inazumi

  3. Otsuka Electronics Co. Ltd., 1-10 Sasagaoka, Minakuchi-cho, Kouka-shi, Shiga, 528-0061, Japan

    Yoshihiro Osawa

Authors
  1. Yoshimi Sueishi
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  2. Ayari Itoh
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  3. Naoya Inazumi
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  4. Yoshihiro Osawa
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  5. Tadashi Hanaya
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Correspondence to Yoshimi Sueishi.

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Sueishi, Y., Itoh, A., Inazumi, N. et al. A comparative study on inclusion complexation of substituted anilinonaphthalene sulfonic acids with 1,6,20,25-tetraaza[6.1.6.1]-paracyclophane and β-cyclodextrin. J Incl Phenom Macrocycl Chem 91, 1–7 (2018). https://doi.org/10.1007/s10847-018-0790-4

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  • DOI: https://doi.org/10.1007/s10847-018-0790-4

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