Skip to main content
SpringerLink
Log in

New Fluorescent Sensors Based on 1H-pyrazolo[3,4-b]quinoline Skeleton

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

Abstract

Novel fluorescing dyes 1,3,4-triphenyl-6-(1,4,7,10-tetraoxa-13-aza-cyclopentadec-13-ylmethyl)-1H-pyrazolo[3,4-b]quinoline (K1) and 2-[(2-hydroxyethyl)-(1,3,4-triphenyl-1H-pyrazolo[3,4-b]quinolin-6-ylmethyl)-amino]ethanol (L1) have been synthesized and investigated by the means of steady state and time-resolved fluorescence techniques. These compounds act as sensors for the fluorescence detection of small inorganic cations (lithium, sodium, barium, magnesium and calcium) in solvents of different polarities (THF and acetonitrile). The mechanism, which allows application of these compounds as sensors, is an electron transfer from the electro-donative part of molecule to the acceptor part (fluorophore), which is retarded upon complexation of the electro-donative part by inorganic cations. We found that crown ether-containing compound is very sensitive to the addition of any investigated ions but amino alcohol-containing one exhibits better selectivity to the addition of two-valued cations. Two kinds of the complexes (LM+ and L2M+) were found in the investigated systems. In addition, the dyes may be used as fluorescence indicators in solvents of lower polarity like tetrahydrofuran.

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

Similar content being viewed by others

References

  1. Valeur B (2002) Molecular fluorescence. Principles and applications. Ch. 10. Wiley-VCH, Weinheim

    Google Scholar 

  2. Li YQ, Bricks JL, Resch-Genger U, Spieles M, Rettig W (2006) J Phys Chem A 110:10972

    Article  CAS  PubMed  Google Scholar 

  3. Leflon P, Plaquet R, Rose F, Hennon G, Ledeme N (1996) Anal Chim Acta 327:301

    Article  CAS  Google Scholar 

  4. Jacobs IA, Taddeo J, Kelly K, Valenziano C (2002) Am J Ind Med 41:285

    Article  PubMed  Google Scholar 

  5. Hung Y-M, Chung H-M (2004) Nephrol Dial Transplant 19:1308

    Article  PubMed  Google Scholar 

  6. Bergamini G, Ceroni P, Balzani V, Cornelissen L, van Heyst J, Lee S-K, Vögtle F (2005) J Mater Chem 15:2959

    Article  CAS  Google Scholar 

  7. Licchelli M, Orbelli Biroli A, Poggi A, Sacchi D, Sangermani C, Zema M (2003) Dalton Trans 4537

  8. Bouas-Laurent H, Castellan A, Daney M, Desvergne JP, Guinand G, Marsau P, Riffaud MH (1986) J Am Chem Soc 108:315

    Article  CAS  Google Scholar 

  9. Yamauchi A, Hayashita T, Nishizawa S, Watanabe M, Teramae N (1999) J Am Chem Soc 121:2319

    Article  CAS  Google Scholar 

  10. Xia WS, Shmehl RH, Li CJ (1999) J Am Chem Soc 121:5599

    Article  CAS  Google Scholar 

  11. Leray I, Habib-Jiwan J-L, Branger C, J-Ph Soumillion, Valeur B (2000) J Photochem Photobiol A Chem 135:163

    Article  CAS  Google Scholar 

  12. Balzani V, Credi A, Venturi M (2003) Molecular device and machines. A journey into the nanoworld. Wiley-VCH Verlag, Weinheim

    Book  Google Scholar 

  13. Chaczatrian K, Chaczatrian G, Danel A, Tomasik P (2003) Polish J Chem 77:1141

    CAS  Google Scholar 

  14. Meech SR, Phillips D (1983) J Photochem 23:193

    Article  CAS  Google Scholar 

  15. Bourson J, Pouget J, Valeur B (1993) J Phys Chem 97:4552

    Article  CAS  Google Scholar 

  16. Barkici H, Koner AL, Nau WM (2005) Chem Commun 5411

  17. Leray I, Lefevre J-P, Delouis J-F, Delaire J, Valuer B (2001) Chem Eur 7:4590

    Article  CAS  Google Scholar 

  18. Rechthaler K, Rotkiewicz K, Danel A, Tomasik P, Köhler G (1997) J Fluoresc 7:301

    Article  CAS  Google Scholar 

  19. Bourson J, Valeur B (1989) J Phys Chem 93:3871

    Article  CAS  Google Scholar 

  20. Petrucci S, Eyring EM (1991) J Phys Chem 95:1731

    Article  CAS  Google Scholar 

  21. Mac M (1997) J Photochem Photobiol A Chem 107:107

    Article  CAS  Google Scholar 

  22. Parvatalu D, Srivastava AK (2008) J Chem Eng Data 53:933

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors would like to thank Prof. Jan Najbar for various assistance during the completion of this project and to Mariusz Kosla for editorial comments.

Author information

Authors and Affiliations

  1. Faculty of Chemistry, Jagiellonian University, Ingardena 3, 30-060, Krakow, Poland

    Marek Mac & Tomasz Uchacz

  2. Student of Faculty of Chemistry, Jagiellonian University, Krakow, Poland

    Tomasz Wróbel

  3. Department of Chemistry, University of Agriculture, Balicka 122, 31-149, Kraków, Poland

    Andrzej Danel & Ewa Kulig

Authors
  1. Marek Mac
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Tomasz Uchacz
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Tomasz Wróbel
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Andrzej Danel
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Ewa Kulig
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Marek Mac.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Mac, M., Uchacz, T., Wróbel, T. et al. New Fluorescent Sensors Based on 1H-pyrazolo[3,4-b]quinoline Skeleton. J Fluoresc 20, 525–532 (2010). https://doi.org/10.1007/s10895-009-0576-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10895-009-0576-6

Keywords

Search

Navigation