Skip to main content
SpringerLink
Log in

Fluorimetric Study on Molecular Recognition of β-cyclodextrin with 2-amino-9-fluorenone

  • Original Paper
  • Published:
Journal of Fluorescence Aims and scope Submit manuscript

Abstract

The molecular recognition interaction of β-cyclodextrin (β-CDx) was investigated using 2-amino-9-fluorenone (2AFN) by UV, steady-state fluorescence and time-resolved fluorescence measurements in aqueous solution at various pH. The effect of acidity on the ground and excited state equilibria between the neutral and the monocationic forms of 2AFN in water and in β-CDx environments are studied. Based on the change in the fluorescence spectrum and lifetimes of 2AFN by the addition of β-CDx, it is found that the unsubstituted part of the 2AFN is encapsulated in the hydrophobic cavity of β-CDx. The unusual red shift obtained for the protonation of amino group in water and β-CDx solution is due to large solvent relaxation of the monocation. The structure of the 1:1 inclusion complex between 2AFN and β-CDx has been proposed on the basis of ground and excited state pK a values and the bond distances obtained by MOPAC/AM 1 data.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11

Similar content being viewed by others

REFERENCES

  1. Liu Y, Li L, Fan Z, Zhang H-Y, Wu X, Liu S-X, Guan X-D (2002) Nanolett 2:257

    CAS  Google Scholar 

  2. Harada A, Li J, Kamachi M (1993) Nature 364:516

    Article  CAS  Google Scholar 

  3. Ikeda E, Okumura Y, Shimomura T, Ito K, Hayakawa R (2000) J Chem Phys 112:4321

    Article  CAS  Google Scholar 

  4. Liu Y, You C-C, Zhang H-Y, Kang S-Z, Zhu C-F, Wang C (2001) Nanolett 1:613

    CAS  Google Scholar 

  5. Anigbogu VC, de la Pena AM, Ndou T, Warner IM (1992) Anal Chem 64:484

    Article  CAS  Google Scholar 

  6. Park JW, Song HE, Lee SY (2003) J Org Chem 68:7071

    Article  PubMed  CAS  Google Scholar 

  7. Shang G, Shuang S, Dong C, Pan J (2003) Spectrochim Acta: A 59:2935

    Article  Google Scholar 

  8. Szejtli J (1982) Cyclodextrins and their inclusion complexes. Akademiai Kiado, Budapest

    Google Scholar 

  9. Li S, Purdy WC (1992) Chem Rev 92:1457

    Article  CAS  Google Scholar 

  10. Hinze WL, Singh HN, Baba Y, Harvey NG (1984) Trends Anal Chem 3:143

    Article  Google Scholar 

  11. Silva AP, Gunarathe HQN, Gulaugsson T, Huxley AJM, Mecoy CP, Rademacher JT, Rice TE (1997) Chem Rev 97:1515

    Article  PubMed  Google Scholar 

  12. Special issue on Cyclodextrins (1998) Chem Rev 98(5):1959–2011

    Article  Google Scholar 

  13. Schlenk W, Fortschr (1951) Chem Soc 83:92

    Google Scholar 

  14. Schlenk W, Sand VM (1961) J Am Chem Soc 83:2312

    Article  CAS  Google Scholar 

  15. Turro NJ, Okubo T (1982) J Am Chem Soc 104:1989

    Google Scholar 

  16. Nakamura A, Sato S, Hamasaki K, Ueno A, Toda F (1995) J Phys Chem 99:10952

    Article  CAS  Google Scholar 

  17. Hamai S (1997) J Phys Chem 10:11707

    Google Scholar 

  18. Park HR, Mayer B, Wolschann P, Kohler G (1994) J Phys Chem 98:6158

    Article  CAS  Google Scholar 

  19. Kosower EM (1986) Ann Rev Phys Chem 37:127 and the references therein

    Article  Google Scholar 

  20. Enoch IMV, Swaminathan M (2004) Collect Czeck Chem Commun 69:748 and the references therein

    Google Scholar 

  21. Enoch IMV, Swaminathan M (2004) J Fluoresc 6:751

    Article  Google Scholar 

  22. Enoch IMV, Swaminathan M (2005) J Incl Phenom Macro Chem 53(3):149–154

    Article  CAS  Google Scholar 

  23. Jorgensonv MJ, Hartter DA (1963) J Am Chem Soc 85:878

    Article  Google Scholar 

  24. Dewar MJS, Zoebisch EG, Healy EF, Stewart JJP (1985) J Am Chem Soc 107:392

    Google Scholar 

  25. Szejtli J (1988) Cyclodextrine technology. Kluwer Academic Publishers, Doedrecht, The Netherlands, pp 143–154

    Google Scholar 

  26. Manoharan R, Dogra SK (1987) Can J Chem 65:2013

    Article  CAS  Google Scholar 

  27. Rajendiran N, Swaminathan M (1995) Bull Chem Soc Jpn 68:2797

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We are thankful to the University Grants Commission, New Delhi for their financial support to the project (Project No: 200. F. 49). We extend our thanks to the National Centre for Ultrafast Processes (NCUFP), University of Madras, Chennai, for fluorescence lifetime measurements. Our thanks are also due to Dr. M. Ramalingam, Sarafoji Government college, Tanjore for his help in the calculation of bond distances using MOPAC/AM 1.

Author information

Author notes

  1. I. V. Muthu Vijayan Enoch

    Present address: Department of Chemistry, Muthayammal College of Arts and Science, Rasipuram, Namakkal District, Tamil Nadu, India

Authors and Affiliations

  1. Department of Chemistry, Annamalai University, Annamalainagar, 608 002, Tamil Nadu, India

    I. V. Muthu Vijayan Enoch & M. Swaminathan

Authors
  1. I. V. Muthu Vijayan Enoch
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. Swaminathan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to M. Swaminathan.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Enoch, I.V.M.V., Swaminathan, M. Fluorimetric Study on Molecular Recognition of β-cyclodextrin with 2-amino-9-fluorenone. J Fluoresc 16, 501–510 (2006). https://doi.org/10.1007/s10895-006-0074-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10895-006-0074-z

keywords

Search

Navigation