Journal of Fluorescence

, Volume 20, Issue 5, pp 1129–1137 | Cite as

Synthesis of Quinolone Substituted Pyrazoles, Isoxazoles and Pyridines as a Potential Blue Luminophors

  • Raghunath B. Toche
  • Muddassar A. Kazi
  • Shivaraj P. Patil
  • Shrikant B. Kanawade
  • Madhukar N. Jachak
Rapid Communication

Abstract

Series of quinolone C3-substituted pyrazolines, isoxazolines, pyridines and pyrimidines were synthesized in good yields by the cyclocondensation reactions of 1, 2-unsaturated ketones and hydrazines, hydroxylamine hydrochloride and dimedone respectively. The quinolone derivatives (3, 5 and 7) were synthesized and further studied for their photophysical properties. High absorption and quantum yield are found for N1-phenyl and C3,4-dimethoxy substituents on phenyl ring (3h). Energy optimization by PM6 methods showed high stability required for selection of suitable candidates to be use as future blue emitters.

Keywords

Dihydropyrazoles Isoxazoles Pyridines Absorption and emission Quantum yields Heat of formation HOMO-LUMO 

Notes

Acknowledgement

Authors thanks to CSIR, New Delhi, for the financial assistance and to the Principal, K.T.H. M. College, Nashik - 422 002 for the facilities.

References

  1. 1.
    Basta AH, Girgis AS, Saied HE (2002) Fluorescent behavior of new 3-pyridinecarbonitrile containing compounds and their application in security paper. Dyes Pigm 54:1–10Google Scholar
  2. 2.
    Kricka LJ (1992) Nonisotopic DNA probe techniques. Academic, New YorkGoogle Scholar
  3. 3.
    Symons RH (1989) Nucleic acid probes. CRC, Boca RatonGoogle Scholar
  4. 4.
    Connolly BA, Newman PC (1989) Synthesis and properties of oligonueclotides containing 4-thiothyniidine, 5-methyl-2-pyrunidinone-1-ß-D(2′-dexoyriboside) and 2-thiothvmidine. Nucleic Acids Res 17:4957–4971CrossRefPubMedGoogle Scholar
  5. 5.
    He Z, Milburn GHW, Baldwin KJ, Smith DA, Danel A, Tomasik P (2000) The efficient blue photoluminescence of pyrazolo-[3, 4-b]-quinoline derivatives and the energy transfer in polymer materials. J Luminensc 86:1–14CrossRefGoogle Scholar
  6. 6.
    He Z, Milburn GHW, Danel A, Puchala P, Tomasik P, Rasala D (1997) Blue electroluminescence of novel pyrazoloquinoline and bispyrazolopyridine derivatives in doped polymer matrices. J Mater Chem 7:2323–2328CrossRefGoogle Scholar
  7. 7.
    Danel A, He Z, Milburn GHW, Tomasik P (1999) Electroluminescence form Novel Pyrazolo based polymer system. J Mater Chem 9:339CrossRefGoogle Scholar
  8. 8.
    Avhale AB, Prokopcova H, Sefcovicova J, Steinschifter W, Taubl AE, Uray G, Stadlbauer W (2008) 4-Cyano-6,7-dimethoxycarbostyrils with solvent- and pH-Independent high fluorescence quantum yields and emission maxima. Eur J Org Chem 17:563–571Google Scholar
  9. 9.
    Badgujar NS, Pazicky M, Traar P, Terec A, Uray G, Stadlbauer W (2006) N-carboxymethylated 6, 7-dimethoxy-4-trifluoromethylcarbostyrils as fluorescence markers for amino acids, peptides, amino carbohydrates and amino polysaccharides. Eur J Org Chem 12:2715–2722CrossRefGoogle Scholar
  10. 10.
    Grabowski ZR, Rotkiewicz K, Siemiarczuk A, Cowely DJ, Baumann W (1979) Nouv J Chim 3:443Google Scholar
  11. 11.
    Kendre DB, Toche RB, Jachak MN (2007) Synthesis of novel dipyrazolo [3, 4-b: 3, 4-d] pyridines and study of their fluorescence behavior. Tetrahedron 63:11000–11004CrossRefGoogle Scholar
  12. 12.
    Ghotekar BK, Kazi MA, Toche RB, Jachak MN (2008) Effect of substituents on absorption and fluorescence properties of pyrazolo [3, 4-b] pyrrolo[2, 3-d] pyridines. Can J Chem 86:1070–1076CrossRefGoogle Scholar
  13. 13.
    Jachak MN, Bagul SM, Ghotekar BK, Toche RB (2009) Synthesis and study of fluorescent behavior of new 3- pyridinecarbonitriles. Monatsh Chem 140:655–662CrossRefGoogle Scholar
  14. 14.
    Toche RB, Kazi MA, Ghotekar BK, Bagul SM, Tantak CD, Jachak MN (2009) Fluorescence properties of donor-acceptor chromophores on newly synthesized pyridine-3-carbonitriles. J Fluoresc 19(6):1119–1124CrossRefPubMedGoogle Scholar
  15. 15.
    Rane BS, Kazi MA, Bagul SM, Toche RB, Jachak MN (2009) Synthesis of novel spiro-oxazino-quinoline derivatives and study of their photophysical properties. J Fluoresc 20(1):415–420CrossRefPubMedGoogle Scholar
  16. 16.
    Abbas M (2000) Chemistry of substituted quinolinones, Part II synthesis of novel 4-pyrazolylquinolinone derivatives. Synth Commun 30:2735CrossRefGoogle Scholar
  17. 17.
    Ibrahim SS, Alimony HA, Othman ES (1997) Chem Papers 51:33Google Scholar
  18. 18.
    Stewart JJP (1989) AM1 calculations were carried out with the MOPAC V5.0 program package. QCPE Bull 9:10, QCPE program no.455Google Scholar

Copyright information

© Springer Science+Business Media, LLC 2010

Authors and Affiliations

  • Raghunath B. Toche
    • 1
  • Muddassar A. Kazi
    • 1
  • Shivaraj P. Patil
    • 1
  • Shrikant B. Kanawade
    • 1
  • Madhukar N. Jachak
    • 1
  1. 1.Organic Chemistry Research Center, Department of ChemistryK. T. H. M. CollegeNashikIndia

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