Skip to main content
Log in

The Solid Channel Structure Inclusion Complex Formed Between Guest Styrene and Host γ-Cyclodextrin

Journal of inclusion phenomena and macrocyclic chemistry Aims and scope Submit manuscript

Abstract

The solid complex of guest styrene included inside the channels of host γ-cyclodextrin (styrene/γ-CDchannel-IC) was formed in order to perform polymerization of styrene in a confined environment (γ-CD channels). The experimental molar ratio of styrene to γ-CD in styrene/γ-CDchannel-IC was found to be 2:1, which is consistent with molecular modeling studies, utilizing Quantum Mechanics PM3 parameters that indicate the γ-CD/two styrene molecular complex is the most energetically favorable. Consistent with modeling of the γ-CD/two styrene molecular complex, no experimental indication of intermolecular π–π interactions between the pairs of included styrene molecules inside the γ-CD channels was observed. Once included in the host γ-CD cavities, the thermal stability of normally volatile bulk styrene to elevated temperatures (much above its boiling point) was observed until the γ-CD host molecules themselves began to degrade at ∼ ∼300 °C. In addition, the thermal degradation of host γ-CD from the styrene/γ-CDchannel-IC was observed to be different from that of pure γ-CD due to co-degradation of styrene and γ-CD.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References:

  1. J. Szejtli, T. Osa, Comp S Chem-V 3: Cyclodextrins Elsevier NY (1996)

    Google Scholar 

  2. X.T. Shuai, F.E. Porbeni, M. Wei, I.D. Shin, A.E. Tonelli, Macromolecules 34(21):7355–7361 2001

    Article  CAS  Google Scholar 

  3. A. Harada, T. Nishiyama, Y. Kawaguchi, M. Okada, M. Kamachi, Macromolecules 30(23):7115 1997

    Article  CAS  Google Scholar 

  4. G.M. Do Nascimento, J.E.P. Da Silva, S.I.C. De Torresi, P.S. Santos, M.L.A. Temperini, Mol. Cryst. Liq. Cryst. 374:53 2002

    Article  CAS  Google Scholar 

  5. M.V. Rekharsky, Y. Inoue, Chem. Rev. 98:1875 1998

    Article  PubMed  CAS  Google Scholar 

  6. H.J. Schneider, F. Hacket, V. Rudiger, Chem. Rev. 98:1755 1998

    Article  PubMed  CAS  Google Scholar 

  7. T. Uyar, M. Rusa, A.E. Tonelli, Macromol. Rapid Commun. 25(15):1382 (2004)

    Article  CAS  Google Scholar 

  8. J. Storsberg, H. van Aert, C. van Roost, H. Ritter, Macromolecules 36(1):50 2003

    Article  CAS  Google Scholar 

  9. J. Storsberg, H. Ritter, Macromol. Rapid Commun. 21(5):236 2000

    Article  CAS  Google Scholar 

  10. J. Storsberg, H. Ritter, H. Pielartzik, L. Groenendaal, Advanced Materials 12(8):567 2000

    Article  CAS  Google Scholar 

  11. Y. Takashima, Y. Oizumi, K. Sakamoto, M. Miyauchi, S. Kamitori, A. Harada, Macromolecules 37:3962 2004

    Article  CAS  Google Scholar 

  12. P. Velusamy, K. Pitchumani, C. Srinivasan, Tetrahedron 52(10):3487 (1996)

    Article  CAS  Google Scholar 

  13. T. Uyar, M.A. Hunt, H.S. Gracz, and A.E. Tonelli: Cryst. Growth+Design (2006) (in review)

  14. T. Uyar and A.E. Tonelli: (in preparation)

  15. G. DiSilvestro, P. Sozzani, M. Farina, Polym. Prepr. 27(1):92 1986

    CAS  Google Scholar 

  16. A.E. Tonelli, Macromolecules 24:3069 (1991)

    Article  CAS  Google Scholar 

  17. M.A. Hunt, D.-W. Jung, M. Shamsheer, T. Uyar, A.E. Tonelli, Polymer 45(4):1345–1347 (2004)

    Article  CAS  Google Scholar 

  18. W.W. Wendlandt, H.G. Hecht, Reflectance Spectroscopy Interscience New York (1966) Chapter 3

    Google Scholar 

  19. J.J.P. Stewart, J. Comp. Chem. 10:221 1989

    Article  CAS  Google Scholar 

  20. M.C. Zerner, Rev. Comput. Chem. 333 (1991) (K.B. Lipkowitz, B.D. Boyed: Vol. 2, VCH)

    Google Scholar 

  21. (a) J.J.P. Stewart: Int. J. Quantum Chem. 58, 133 (1999) (b) CAChe Worksystem Pro Version 6.1.12.33, Fujitsu America Inc., Beaverton, OR 97006–5733

    Google Scholar 

  22. K. Harata: Crystallographic Studies, Vol. 3, Comprehensive Supramolecular Chemistry; J.L. Atwood, J.E. Davies, D.D. MacNicol, F. Vogtle, J.M. Lehn: (eds.), Pergamon, Oxford, (1996)

  23. W. Saenger, J. Jacob, K. Gessler, T. Steiner, D. Hoffmann, H. Sanbe, K. Koizumi, S.M. Smith, T. Takaha, Chem. Rev. 98:1787 1998

    Article  PubMed  CAS  Google Scholar 

  24. C.C. Rusa, M. Rusa, M. Gomez, I.D. Shin, J.D. Fox, A.E. Tonelli, Macromolecules 37(21):7992 2004

    Article  CAS  Google Scholar 

  25. T. K. Lind, T. Kuge, Agr. Biol. Chem. 34(4):568 (1970)

    Google Scholar 

  26. T. Uyar, C.C. Rusa, M.A. Hunt, E. Aslan, J. Hacaloglu, A.E. Tonelli, Polymer 46(13):4762, (2005)

    CAS  Google Scholar 

  27. T. Uyar, L. Toppare, J. Hacaloglu, Macromol. Rapid. Commun. 22(3):199 (2001)

    Article  CAS  Google Scholar 

  28. T. Uyar, L. Toppare, J. Hacaloglu, J. Anal. Appl. Pyrol. 68–69:15 (2003)

    Article  CAS  Google Scholar 

  29. T. Uyar, L. Toppare, J. Hacaloglu, J. Macromol. Sci-Pure Appl. Chem. 38(11) 1141 2001

    Article  Google Scholar 

  30. T. Uyar, E. Aslan, A.E. Tonelli, and J. Hacaloglu: Polym. Degrad. Stabil. (2005) (In press)

  31. R. Breslow, S.D. Dong, Chem. Rev. 98:1998 (1997)

    Google Scholar 

  32. (a) K.B. Lipkowitz: Chem. Rev. 98, 1829 (1998) (b) L. Liu, Q.-X. Guo: J. Phys. Chem. B. 103, 3461 (1999) (c) H. Dodziuk, O. Lukin, and K.S. Nowinski: J. Mol. Struct. (Theochem). 503, 221 (2000)

  33. P. Bonnet, C. Jaime, L. Morin-Alloy, J. Org. Chem. 66:689 2001

    Article  PubMed  CAS  Google Scholar 

  34. (a) G. Grabner, S. Monti, B. Mayer, and G. Koehler: J. Phys. Chem. 100, 68 (1996) (b) H. Tanaka, N. Kato, and H. Kawazura: Bull. Chem. Soc. Jpn 70, 1255 (1997)

  35. M. Kitagawa, H. Hoshi, M. Sakurai, Y. Inoue, R. Chujo, Carbohydr. Res. 283 1987

    Google Scholar 

  36. A. Bosti, K. Yannakopoulou, E. Hadjoudis, J. Waite, Carbohydr. Res. 283:1 1996

    Article  PubMed  Google Scholar 

  37. (a) M.J. Huang, J.D. Watts, and N. Bodor: Int. J. Quantum Chem. 64, 711 (1997) (b) M.J. Huang, J.D. Watts, and N. Bodor: Int. J.␣Quantum Chem. 65, 1135 (1997)

  38. R. Castro, M.J. Berardi, E. Cordova, M.O. Deolza, A.E. Kaifer, J.D. Evanseck, J. Am. Chem. Soc. 118:10257 (1996)

    Article  CAS  Google Scholar 

  39. H. Shiozaki, M. Matsuoka, J. Mol. Struct. (Theochem) 427:253 (1988)

    Article  Google Scholar 

Download references

Acknowledgements

The authors are grateful to the National Textile Center (US Dept. of Commerce) for funding. The authors would also thank North Carolina State University and the Middle East Technical University (Ankara, Turkey) for their support. We also thank Evren Aslan, and Michael D. Capracotta for performing the Direct Insertion Probe Pyrolysis Mass Spectrometry (DIP-MS) and solid-state UV-Vis experiments, respectively.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Alan E. Tonelli.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Uyar, T., El-Shafei, A., Wang, X. et al. The Solid Channel Structure Inclusion Complex Formed Between Guest Styrene and Host γ-Cyclodextrin. J Incl Phenom Macrocycl Chem 55, 109–121 (2006). https://doi.org/10.1007/s10847-005-9026-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10847-005-9026-5

Keywords

Navigation