Skip to main content
SpringerLink
Log in

Azo-hydrazo Tautomerism and Inclusion Complexation of 1-phenylazo-2-naphthols with Various Solvents and β-cyclodextrin

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

Abstract

Spectral characteristics of sudan I (SDI), sudan II (SDII) and mordant violet-5 (MV5) have been studied in various solvents and β-cyclodextrin (β-CD). The inclusion complex of the above molecules with β-CD was analyzed by UV-visible, fluorometry, and DFT methods. The solvent study shows that azo-hydrazo tautomer is present in these molecules. The increase in the fluorescence intensity and a large bathochromic shift in the S1 state indicate these molecules forms 1:1 inclusion complex with β-CD.

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

Similar content being viewed by others

References

  1. Zince T, Binderwald M (1884) Chem Ber 17:3026

    Article  Google Scholar 

  2. Gregory P (1991) High-technology applications of organic colorants. Kluwer Academic, Amsterdam

    Google Scholar 

  3. Carter LF, Schultz A, Dukkworth D (1987) In: Carter FL (ed) Molecular electronic devices II. Marcel Decker, New York, p 183

    Google Scholar 

  4. Zollinger H (2009) Colour chemistry, synthesis, properties and applications of organic dyes and pigments, 3rd edn. Verlag Helvetica Chimica Acta, Zurich, p 429

    Google Scholar 

  5. Antonov L, Fabian FMW, Taylor JP (2005) J Phys Org Chem 18:1169

    Article  CAS  Google Scholar 

  6. Antonov L, Kawauchi S, Satoh M, Komiyama J (1999) Dyes Pigm 40:163

    Article  CAS  Google Scholar 

  7. Antonov L, Nedeltcheva D (2009) Chem Soc Rev 29:217

    Article  Google Scholar 

  8. Antonov L, Stoyanov S, Stoyanova T (1995) Dyes Pigm 27:133

    Article  CAS  Google Scholar 

  9. Szejtli J, Osa T (1996) In: Atwood JL, Davies JE, MacNicol DD, Vogtle F (eds) Comprehensive supramolecular chemistry, vol 3. Pergamon/Elsevier, Oxford

    Google Scholar 

  10. Meo PL, Anna FD, Riela S, Gruttadauria M, Noto RR (2003) Org Biomol Chem 1:1584

    Article  PubMed  CAS  Google Scholar 

  11. Antony Muthu Prabhu A, Rajendiran N (2009) Spectrochim Acta 74:484–497

    Article  CAS  Google Scholar 

  12. Antony Muthu Prabhu A, Rajendiran N (2010) J Fluoresc 20:43–54

    Article  PubMed  CAS  Google Scholar 

  13. Craig MR, Hutchings MG, Claridge TDW, Anderson HL (2001) Angew Chem Int Ed 40:1071

    Article  CAS  Google Scholar 

  14. Takei M, Yui H, Hirose Y, Sawada T (2001) J Phys Chem 105A:11395

    Google Scholar 

  15. Bortolus P, Monti S (1987) J Phys Chem 91:5046

    Article  CAS  Google Scholar 

  16. Yoshida N, Seiyama A, Fujimoto M (1990) J Phys Chem 94:4246

    Article  CAS  Google Scholar 

  17. Yoshida N, Yamauchi H, Higashi M (1998) J Phys Chem 102:1523

    CAS  Google Scholar 

  18. Sanchez AM, de Rossi RH (1996) J Org Chem 61:3446

    Article  CAS  Google Scholar 

  19. Abou-Hamdan A, Bugnon P, Saudan C, Lye PG, Merbach AE (2000) J Am Chem Soc 122:592

    Article  CAS  Google Scholar 

  20. Kuwabara T, Nakajima H, Nanasawa M, Ueno A (1999) Anal Chem 71:2844

    Article  CAS  Google Scholar 

  21. Kuwabara T, Aoyagi T, Takamura M, Matsushita A, Nakamura A, Ueno A (2002) J Org Chem 67:720

    Article  PubMed  CAS  Google Scholar 

  22. Liu Y, Zhao YL, Zhang HY, Fan Z, Wen GD, Ding F (2004) J Phys Chem 108B:883

    Google Scholar 

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

    Google Scholar 

  24. Durr H, Boves-Laurenet H (1990) Photochromism and systems (eds) Elsevier Amsterdam

  25. Tawa K, Kamada K, Ohta K (2000) J Photochem Photobiol A Chem 34:185

    Article  Google Scholar 

  26. Nishimura N, Tanaka T, Asano M, Sueishi Y (1986) J Chem Soc Perkin Trans 2:1839

    Google Scholar 

  27. Yoshida N, Fujita Y (1995) J Phys Chem 99:3671

    Article  CAS  Google Scholar 

  28. Connors KA, Mulski MJ, Paulson A (1992) J Org Chem 57:1794

    Article  CAS  Google Scholar 

  29. Antony Muthu Prabhu A, Rajendiran N (2010) Indian Journal of Chemistry 49A, in press

  30. Antonov L, Fabian MFW, Nedeltcheva D, Kamounan FS (2000) J Chem Soc Perkin Trans 2:1173

    Google Scholar 

  31. Gu Y, Kar T, Scheiner S (1999) J Am Chem Soc 121:9411

    Article  CAS  Google Scholar 

  32. Gilli P, Bertolasi V, Pretto L, Lycka A, Gilli G (2002) J Am Chem Soc 124:13554

    Article  PubMed  CAS  Google Scholar 

  33. Buemi G, Zuccerello F (2002) J Mol Struct Theochem 581:71

    Article  CAS  Google Scholar 

  34. Fabian WMF, Antonov L, Nedeltcheva D, Kamounan FS, Taylor PJ (2004) J Phys Chem 108A:7603

    Google Scholar 

  35. Zollingser H (1991) Colour chemistry, synthesis, properties and applications of organic dyes and pigments. VCH, Weinheim

    Google Scholar 

  36. Alarcon SH, Olivieri AC, Labadie GR, Craveno R, Gunzales Sierra M (1995) Tetrahedron 51:4619

    Article  CAS  Google Scholar 

  37. Joshi H, Kamounah FS, Gooijer C, van der Zwan G, Antonov L (2002) J Photochem Photobiol A Chem 152:183

    Article  CAS  Google Scholar 

  38. Rettig W, Lapouyade R (1995) In: Lakowicz JR (ed) Topics in fluorescence spectroscopy: probe design and chemical sensing, vol 4. Plenum, New York, p 116

    Google Scholar 

  39. Biolot L, Kawasaki A (1962) Z Naturforsch 17A:621

    Google Scholar 

  40. Reichardt C, Dimorth K (1968) Fort Schr Chem Forsch 11:1

    Article  CAS  Google Scholar 

  41. Jiang YB (1994) Appl Spectrosc 48:1169

    Article  Google Scholar 

  42. Cho DW, Kim YH, Kang SG, Yoon M, Kim D (1996) J Chem Soc Faraday Trans 92:29

    Article  CAS  Google Scholar 

  43. Chow DW, Kim YH, Kang SG, Yoon M (1996) J Phys Chem 100:15670

    Article  Google Scholar 

  44. Benesi A, Hildebrand JH (1949) J Am Chem Soc 71:2703

    Article  CAS  Google Scholar 

  45. Hamai S (1982) Bull Chem Soc Jpn 55:2721

    Article  CAS  Google Scholar 

  46. Kano K, Tawiya Y, Hashimoto S (1992) J Incl Phenom 3:287

    Google Scholar 

  47. Tabushi I (1984) Tetrahedron 40:269

    Article  CAS  Google Scholar 

  48. Guo Q-X, Luo S-H, Liu Y-C (1998) J Incl Phenom Mol Recognit Chem 30:173

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  50. Connors KA, Lin SF, Wong AB (1982) J Pharm Sci 71:217

    Article  PubMed  CAS  Google Scholar 

  51. Davies DM, Deary ME (1995) J Chem Soc Perkin Trans 2:1287

    Google Scholar 

  52. Wenz G (1994) Angew Chem Int Ed Engl 33:803

    Article  Google Scholar 

  53. Kitagawa M, Hoshi H, Sakurai M, Inoue Y, Chujo R (1987) Carbohydr Res 163:c1

    Article  CAS  Google Scholar 

  54. Sakurai M, Kitagawa M, Inoue Y, Chujo R (1990) Carbohydr Res 198:181

    Article  CAS  Google Scholar 

  55. Delaage M (1991) In: Delaage M (ed) Molecular recognition mechanisms, ch 1. VCH, New York

    Google Scholar 

Download references

Acknowledgement

This work is supported by the Department of Science and Technology, New Delhi, (Fast Track Proposal Young Scientist Scheme No. SR/FTP/CS-14/2005) and University Grants Commission, New Delhi (Project No. F-31-98/2005 (SR)).

Author information

Authors and Affiliations

  1. Department of Chemistry, Annamalai University, Annamalai Nagar, 608 002, Tamilnadu, India

    A. Antony Muthu Prabhu, G. Venkatesh & N. Rajendiran

Authors
  1. A. Antony Muthu Prabhu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. G. Venkatesh
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. N. Rajendiran
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to N. Rajendiran.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Antony Muthu Prabhu, A., Venkatesh, G. & Rajendiran, N. Azo-hydrazo Tautomerism and Inclusion Complexation of 1-phenylazo-2-naphthols with Various Solvents and β-cyclodextrin. J Fluoresc 20, 961–972 (2010). https://doi.org/10.1007/s10895-010-0642-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10895-010-0642-0

Keywords

Search

Navigation