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Stoichiometrically Different Inclusion Complexes of 2-Aminofluorene and 2-Amino-9-Hydroxyfluorene in β-Cyclodextrin: A Spectrofluorimetric Study

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Abstract

β-cyclodextrin (β-CDx) forms inclusion complexes with 2-aminofluorene (2AF) and 2-amino-9-hydroxyfluorene (2AHF) in different stoichiometries (Guest-host ratio 1:1 and 1:2 respectively) which is discussed on the basis of study by absorption and fluorescence spectroscopy. The ground and the excited state acidity constants for the neutral‒monocation equilibrium of the two fluorophores in aqueous β-CDx medium are determined by spectrophotometric and fluorimetric titration methods respectively. The dual fluorescence observed for 2AHF monocation in aqueous solution is due to the formation of monocation-water exciplex. This monocation-water exciplex formation is hindered in β-CDx solution by the inclusion complexation. Based on the results obtained, the structures of the inclusion complexes are proposed.

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References

  1. Saenger W (1984) In: Atwood JL, Davies JED, MacNicol DD (eds) Inclusion compounds, vol 2. Academic Press, p 231

  2. Bender ML, Komiyama M (1978) Cyclodextrin chemistry. Springer, Berlin

    Google Scholar 

  3. Saenger W (1980) Angew Chem Intl Ed Engl 19:334

    Google Scholar 

  4. Puglisi G, Sanatagati NA, Pignatello R (1990) Drug Dev Ind Pharm 16:395

    CAS  Google Scholar 

  5. Matsushima M (1994) Japan Patent 94:343, 419

  6. Microgenic Corp (1989) EU Patent 301:847l

  7. Sanchez FG, Lopez MH, Gomez JCM (1987) Analyst 112:1037

    Article  Google Scholar 

  8. Escander GM (1999) Analyst 124:587–591

    Article  Google Scholar 

  9. Escander GM, Munoz de la Pena A (1998) Anal Chim Acta 370:199

    Article  Google Scholar 

  10. Araniciba JA, Escander GM (1999) Analyst 124:1833

    Article  Google Scholar 

  11. Shizuka H (1985) Acc Chem Res 18:141, and the references therein

    Article  CAS  Google Scholar 

  12. Swaminathan M, Dogra SK (1983) J Am Chem Soc 105:6223

    Article  CAS  Google Scholar 

  13. Dey JK, Dogra SK (1990) Chem Phys 143:97

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  15. Shizuka H, Ogiwara T, Kimuro E (1985) J Phys Chem 89:4302

    Article  CAS  Google Scholar 

  16. Manoharan R, Dogra SK (1988) Can J Phys Chem 92:5282

    Article  CAS  Google Scholar 

  17. Muthu Vijayan Enoch IV, Swaminathan M (2004) Collect Czeck Chem Commun 69:748

    Article  CAS  Google Scholar 

  18. Muthu Vijayan Enoch IV, Swaminathan M (2004) J Fluorescence 6:751

    Article  Google Scholar 

  19. Muthu Vijayan Enoch IV, Swaminathan M (2005) J Inclusion Phenom Macrocyclic Chem 53:149

    Article  Google Scholar 

  20. Ritchol H, Fitch BR (1974) Anal Chem 46:1749

    Article  Google Scholar 

  21. Saha SK, Dogra SK (1998) J Molec Struc 470:301

    Article  CAS  Google Scholar 

  22. Jorgenson M, Hartter DR (1963) J Am Chem Soc 85:878

    Article  CAS  Google Scholar 

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

    Google Scholar 

  24. Szejtli J (1988) Cyclodextrin technology. Kluwer Academic Publishers, Doedrecht, The Netherlands, p 143

    Google Scholar 

  25. Cho DW, Kim YH, Kang SK, Yoon M, Kim DJ (1996) J Chem Soc, Faraday Trans 92:29

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  27. Kalaiyarasan K, Rajendran N, Swaminathan M (1994) Indian J Chem 33A:335

    CAS  Google Scholar 

  28. Rajendiran N, Swaminathan M (1995) Bull Chem Soc Jpn 69:2447

    Article  Google Scholar 

Download references

Acknowledgments

We are thankful to the University Grants Commission for their financial assistance (Project No. 200.F.49) and to the National Centre for Ultrafast Processes, University of Madras, Chennai for their help in taking fluorescence lifetime measurements.

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Authors and Affiliations

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

    I. V. Muthu Vijayan Enoch & M. Swaminathan

  2. Muthayammal college of Arts and Science, Rasipuram, Namakkal District, Tamil Nadu, India

    I. V. Muthu Vijayan Enoch

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  1. I. V. Muthu Vijayan Enoch
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  2. M. Swaminathan
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Correspondence to M. Swaminathan.

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Enoch, I.V.M.V., Swaminathan, M. Stoichiometrically Different Inclusion Complexes of 2-Aminofluorene and 2-Amino-9-Hydroxyfluorene in β-Cyclodextrin: A Spectrofluorimetric Study. J Fluoresc 16, 697–704 (2006). https://doi.org/10.1007/s10895-006-0112-x

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  • DOI: https://doi.org/10.1007/s10895-006-0112-x

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