Skip to main content
SpringerLink
Log in

Intramolecular Proton Transfer Effects on 2,6-diaminopyridine

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

Abstract

The photophysical behaviour of 2,6-diaminopyridine (DAP) has been studied in solvents of different polarity, pH, β-cyclodextrin (β-CD) and compared with 2-amino pyridine (2AP). The inclusion complex of both molecules with β-CD are analysed by UV-visible, fluorimetry, FT-IR, 1H NMR, SEM and AM1 methods. The solvent studies shows i) DAP gives more red shifted absorption and emission maxima than 2AP molecule and ii) addition of amino group in 2AP effectively increase the resonance interaction in the pyridine ring. A regular red shift observed in acidic pH solutions suggests intramolecular proton transfer (IPT) present in both molecules. β-CD studies indicates i) in pH  ~ 7, a regular red shifted absorption and emission maxima observed in AP molecules suggests pyridine ring encapsulated in to the β-CD cavity (1:1 inclusion complex formed) and ii) in pH ~ 1, a blue shifted absorption maxima noticed in 2AP, is due to protonated amino group deeply encapsulated in to the hydrophobic part of the β-CD cavity.

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

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Scheme 2
Fig. 8

Similar content being viewed by others

References

  1. Schulman SG (1974) In: Kortitzky AR (ed) Physical methods in heterocyclic chemistry, vol VI. Academic, New York, p 193

    Google Scholar 

  2. Barni P, Savarino P, Viscardi G (1991) Trends Heterocycl Chem 2:27

    CAS  Google Scholar 

  3. Brand L, Gohlka JR (1972) Annu Rev Biochem 41:843

    Article  CAS  PubMed  Google Scholar 

  4. Klose G, Stelzmer F (1974) Biochem Biophys Acta 1:363

    Google Scholar 

  5. Smets J, Maes G (1991) Chem Phys Lett 187:532

    Article  CAS  Google Scholar 

  6. Brown RS, Tse A, Vaderas JC (1980) J Am Chem Soc 102:1174

    Article  CAS  Google Scholar 

  7. Kwiatkowski JS, Bartlett RJ, Person WB (1988) J Am Chem Soc 110:2353

    Article  CAS  Google Scholar 

  8. King ST, Oilling DL, Teferkiller NB (1972) Tetrahedron 28:5859

    Article  CAS  Google Scholar 

  9. Cox RH, Bothner AA (1969) J Phys Chem 73:2465

    Article  CAS  Google Scholar 

  10. Krebs C, Hofmann H, Kohler HJ, Weiss C (1980) Chem Phys Lett 69:537

    Article  CAS  Google Scholar 

  11. Mitra S, Das R, Mukherjee S (1994) Spectrochim Acta 50A:1301

    CAS  Google Scholar 

  12. Mitra S, Das R, Mukherjee S (1994) J Photochem Photobiol 79:49

    Article  CAS  Google Scholar 

  13. Mitra S, Das R, Mukherjee S (1999) J Lumin 81:61

    Article  Google Scholar 

  14. Will G, Mukherjee S et al (1999) Indian J Chem 38A:753

    CAS  Google Scholar 

  15. Jorgenson MJ, Hartter DA (1963) J Am Chem Soc 85:878

    Article  CAS  Google Scholar 

  16. Yagil G (1967) J Phys Chem 71:1054

    Google Scholar 

  17. Marckwald G (1894) Berlin J 27:1321

  18. EA Steck, Ewing GW (1948) J Am Chem Soc 3397

  19. Maier-Bode H, Altpeter J (1934) Das Pyridin und seine derivate Knapp, Halle, p 91

  20. Tway PC, Love LJC (1982) J Phys Chem 86:5223

    Article  CAS  Google Scholar 

  21. Dey JK, Warner IM (1998) J Photochem Photobiol A: Chem 116:27

    Article  CAS  Google Scholar 

  22. Biswas A, Dey JK (2001) Indian J Chem 40A:1143

    CAS  Google Scholar 

  23. Lim EC (1977) In: Lim EC (ed) Excited states, vol 3. Academic, New York, p 305

    Google Scholar 

  24. Hochstrasser RM, Merzzacco CA (1969) In: Lim EC (ed) Molecular luminescence. W.A. Berjamin Inc, New York, p 631

    Google Scholar 

  25. Lippert E (1955) Z Naturforsch 10A:541

    CAS  Google Scholar 

  26. Biolet L, Kawski A (1962) Z Naturforsch 17A:621

    Google Scholar 

  27. Reichardt C, Dimroth K (1968) Forstschr Chem Forsch 11:1

    Article  CAS  Google Scholar 

  28. Rajendiran N, Swaminathan M (1995) J Photochem Photobiol A: Chem 90:109

    Article  CAS  Google Scholar 

  29. Rajendiran N, Swaminathan M (1996) Bull Chem Soc Jpn 69:2447

    Article  CAS  Google Scholar 

  30. Rajendiran N, Swaminathan M (1996) Indian J Chem 35A:818

    CAS  Google Scholar 

  31. Rajendiran N, Swaminathan M (1995) Bull Chem Soc Jpn 68:2802

    Article  Google Scholar 

  32. Rajendiran N, Swaminathan M (1996) J Photochem Photobiol A: Chem 93:103

    Article  CAS  Google Scholar 

  33. Stalin T, Rajendiran N (2007) Spectrochim Acta 68A:894

    Google Scholar 

  34. Stalin T, Rajendiran N (2008) Spectrochim Acta 69A:822

    Google Scholar 

  35. Stalin T, Rajendiran N (2006) J Mol Struct 795:35

    Article  Google Scholar 

  36. Stalin T, Rajendiran N (2006) Chem Phys 322:311

    Article  CAS  Google Scholar 

  37. Stalin T, Rajendiran N (2006) J Photochem Photobiol A: Chem 18:137

    Article  Google Scholar 

  38. Stalin T, Rajendiran N (2006) J Incl Phenom Macrocycl Chem 55:21

    Article  CAS  Google Scholar 

  39. Krishnamoorthy G, Dogra SK (1999) J Photochem Photobiol A: Chem 123:109

    Article  CAS  Google Scholar 

  40. Das S (2002) Chem Phys Lett 361:21

    Article  CAS  Google Scholar 

  41. Kim TH, Cho DW, Yoon M, Kim D (1996) J Phys Chem 160:15670

    Article  Google Scholar 

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

    Article  Google Scholar 

  43. Jiang TB (1995) J Photochem Photobiol A: Chem 88:109

    Article  CAS  Google Scholar 

  44. Agbaria RA, Uzar B, Gill D (1989) J Phys Chem 93:3855

    Article  CAS  Google Scholar 

  45. Benesi HA, Hildebrand JH (1949) J Am Chem Soc 71:2703

    Article  CAS  Google Scholar 

  46. Senger M (1984) In: Atwood JL, Davies JED, Macnicol DD (eds) Inclusion complexes, vol 2. Academic, London, p 231

    Google Scholar 

  47. Lehman J, Klienpeter E (1991) J Incl Phenom 10:233

    Article  Google Scholar 

  48. Inoue Y, Kuan F, Chujo R (1987) Bull Chem Soc Jpn 60:253

    Google Scholar 

  49. Chao JB, Tong HB, Huang SP, Lie DS (2004) Spectrochim Acta 60A:161

    CAS  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, S. Siva, R. K. Sankaranarayanan & N. Rajendiran

Authors
  1. A. Antony Muthu Prabhu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. Siva
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. R. K. Sankaranarayanan
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. 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

Prabhu, A.A.M., Siva, S., Sankaranarayanan, R.K. et al. Intramolecular Proton Transfer Effects on 2,6-diaminopyridine. J Fluoresc 20, 43–54 (2010). https://doi.org/10.1007/s10895-009-0520-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10895-009-0520-9

Keywords

Search

Navigation