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Synthesis and Fluorescence Properties of Donor-Acceptor-Substituted Novel Dipyrazolo[3,4-b:3′,4′-d]Pyridines (DPP)

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Abstract

A rapid and efficient method for the synthesis of novel dipyrazolo[3,4-b:3′,4′-d]pyridines (DPP) from pyrazolo[3,4-b]pyridine was successfully developed. The DPP derivative was further N-alkylated (6, 8) as well as N-linked with amino acids (13) and their photophysical properties were studied along with N-aryl DPP 4 and observed that the chromophores at C4 position in the aryl ring changed the absorption and emission λmax.

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References

  1. Tang C, Vanslyke S (1987) Organic electroluminescent diodes. Appl Phys Lett 51:913–915

    Article  CAS  Google Scholar 

  2. Ohmori Y, Uchida M, Muro K, Yoshino K (1991) Blue electroluminescent diodes utilizing poly(alkylfluorene). Jpn J Appl Phys 30:L1941–L1943

    Article  Google Scholar 

  3. Kido J, Honggawa K, Okuyama K, Nagai K (1993) Bright blue electroluminescence from poly(N-vinylcarbazole). Appl Phys Lett 63:2627–2629

    Article  CAS  Google Scholar 

  4. Miyata S, Nalwa H (1997) Organic electroluminescent materials and devices. Gorden and Breach, Amsterdam

    Google Scholar 

  5. Bradley D (1996) Electoluminescent polymers: materials, physics and device engineering. Curr Opin Solid State Mater Sci 1:789–797

    Article  CAS  Google Scholar 

  6. Rechthaler K, Schamschule R, Parusel A, Rotkiewicz K, Piorun D, Koehler G (1999) Fluorescence properties of an electron acceptor-substituted bis-pyrazolopyridine derivative, NO2-DMPP. Acta Phys Polon A 95:321–334

    CAS  Google Scholar 

  7. Miyasaka H, Itaya A, Rotkiewicz K, Rechthaler K (1999) Picosecond laser photolysis studies of DMA-DMPP in solution. Chem Phys Lett 307:121–130

    Article  CAS  Google Scholar 

  8. Parusel ABJ, Schamschule R, Kohler G (1998) Theoretical description of solvent effects on fluorescence spectra of bulky charge transfer compound DMA-DMPP. J Comput Chem 19:1584–1595

    Article  CAS  Google Scholar 

  9. Parusel ABJ, Schamschule R, Kohler G, Bunsenges B (1997) A semiempirical study of fluorescence properties of large charge transfer compounds: N, N-dimethylanilino-bis-pyrazolopyridine. Phys Chem 101:1836–1843

    CAS  Google Scholar 

  10. Balasubramaniam E, Tao Y, Danel A, Tomasik P (2000) Blue light-emitting diodes based on dipyrazolopyridine derivatives. Chem Mater 12:2788–2793

    Article  CAS  Google Scholar 

  11. Tao Y, Chuen C, Ko C, Peng J (2002) Efficient blue light-emitting diodes based on triarylamine-substituted dipyrazolopyridine derivatives. Chem Mater 14:4256–4261

    Article  CAS  Google Scholar 

  12. Piorun D, Parusel A, Rechthaler K, Rotkiewicz K, Kohler G (1999) Acid-base properties of bis-pyrazolopyridine derivatives in nonaqueous solutions. J Photochem Photobiol A: Chem 129:33–41

    Article  CAS  Google Scholar 

  13. 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 63:11000–11004

    Article  CAS  Google Scholar 

  14. Ghotekar KB, Kazi MA, Jachak MN, Toche RB (2007) Effect of substituents on absorption and fluorescence properties of pyrazolo[3, 4-b]pyrrolo[2, 3-d]pyridines. Can J Chem 86:1070–1076

    Article  Google Scholar 

  15. Hoehn H, Denzel T, Janssen W (1972) 1H-pyrazolo[3, 4-b]pyridines. J Heterocycl Chem 9:235–253

    Article  CAS  Google Scholar 

  16. Danishefsky S, Allen J (2000) A reterospective on fully synthetic carbohydrate-based anticancer vaccines. Angew Chem Int Ed 39:836–863

    Article  CAS  Google Scholar 

  17. David R, Machova Z, Beck-Sickinger A (2003) Semisynthesis and application of carboxyfluorescein-labelled biologically active human interleukin-8. Biol Chem 384:1619–1630

    Article  CAS  PubMed  Google Scholar 

  18. Fuchs S, Otto H, Jehle S, Henklein P, Schuter A (2005) Fluorescent dendrimers with a peptide cathepsin B cleavage site for drug delivery applications. Chem Commun 14:1830–1832

    Article  Google Scholar 

  19. Faure M, Gaudreau P, Shaw I, Cashman N, Beaudet A (1994) Synthesis of a biologically active fluorescent probe for labeling neurotensin receptors. J Histochem Cytochem 42:755

    CAS  PubMed  Google Scholar 

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Acknowledgements

The authors thank UGC, New Delhi, India, for financial support of this research project. We thank Professor D. D. Dhavale, Department of Chemistry, University of Pune, India, for his valuable cooperation for the measurements of fluorescence properties. The Authors also thanks to Principal, KTHM College, Nashik-422 002 for facilities.

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Authors and Affiliations

  1. Organic Chemistry Research Center, Department of Chemistry, K.R.T. Arts, B.H. Commerce and A.M. Science College, Gangapur Road, Nashik, 422002, MS, India

    Madhukar N. Jachak, Sandeep M. Bagul, Dilip R. Birari, Maruti G. Ghagare, Muddassar A. Kazi & Raghunath B. Toche

  2. Mega Fine Pharma Pvt. Ltd., 201, Lakhmapur, Dindori, Nashik, 422202, MS, India

    Vijayavitthal T. Mathad

Authors
  1. Madhukar N. Jachak
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  2. Sandeep M. Bagul
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  3. Dilip R. Birari
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  4. Maruti G. Ghagare
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  5. Muddassar A. Kazi
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  6. Raghunath B. Toche
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  7. Vijayavitthal T. Mathad
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Correspondence to Madhukar N. Jachak.

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Jachak, M.N., Bagul, S.M., Birari, D.R. et al. Synthesis and Fluorescence Properties of Donor-Acceptor-Substituted Novel Dipyrazolo[3,4-b:3′,4′-d]Pyridines (DPP). J Fluoresc 20, 787–796 (2010). https://doi.org/10.1007/s10895-010-0622-4

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  • DOI: https://doi.org/10.1007/s10895-010-0622-4

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