Skip to main content
SpringerLink
Log in

Developing of Fluorescence Probes Based on Stilbazolium Salts for Monitoring Free Radical Polymerization Processes. II

  • Published:
Journal of Fluorescence Aims and scope Submit manuscript

Abstract

The series of 1-methyl-4-(4-aminostyryl)pyridinium perchlorates was investigated as fluorescent probes for the monitoring of the free radical polymerization progress. The study on the changes in fluorescence intensity and spectroscopic shifts of studied compounds were carried out during thermally initiated polymerization of methyl methacrylate. The purpose of these studies was to find a relationship between the structure of fluorophore and the changes in their fluorescence shape and intensity observed during the monomer conversion into polymer. The probes under the study during the course of polymerization increase their fluorescence intensity at least one order of magnitude. Such increase qualified the tested probes as good fluorescence probes.

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

Similar content being viewed by others

References

  1. Y. Nishijima and Y. Mito (1967). in J. Guillet (Ed.) Polymer Photophysics and Photochemistry, Cambridge University Press, Cambridge, MA, Chap. 6 and references therein.

    Google Scholar 

  2. Y. Nishijima (1970). Fluorescence methods in polymer science. J. Polym. Sci. Part C 31, 353-373.

    Google Scholar 

  3. Y. Nishijima (1962). in H. Kallmann and G. S. Spruch (Eds.), Luminescence of Organic and Inorganic Materials, Wiley, New York, p. 235.

    Google Scholar 

  4. R. O. Loutfy (1981). Spectroscopy of dyes in polymer matrices: Dual fluorescence of a [p-(dialkylamino)benzylidene]malonitrile dye in poly(vinylacetate) matrices. Macromolecules 14, 270.

    Google Scholar 

  5. R. O. Loutfy (1982). Fluorescence probes for polymerization reactions: Bulk polymerization of styrene, n-butyl methacrylate, ethyl methacrylate, and ethyl acrylate. J. Polym. Sci. Phys. 20, 825.

    Google Scholar 

  6. R. O. Loutfy (1986). Fluorescence probes for polymer free-volume. Pure Appl. Chem. 58, 1239.

    Google Scholar 

  7. D. Cho, W. L. Mattice, L. J. Porter, and R. W. Hemingway (1989). Use of the fluorescence quantum yield for the determination of the number-average molecular weight of polymers of epicatechin with 4β →8 interflavon bonds. Polymer 30, 1955.

    Google Scholar 

  8. P. V. Kamat (1987). Fluorescence emission as a probe to investigate electrochemical polymerization of 9-vinylanthracene. Anal. Chem. 59, 1636.

    Google Scholar 

  9. P. V. Kamat and S. K. Gupta (1988). Electropolymerization of 9-vinylanthracene: Kinetic study using thin-layer spectroschemistry. Polymer 29, 1329.

    Google Scholar 

  10. H. J. van Ramesdonk, M. Vos, J. V. Verhoeven, G. R. Möhlman, N. A. Tissink, and A. W. Meesen (1987). Intramolecular charge-transfer fluorescence as a mobility probe in poly(methylmethacrylate). Polymer 28, 951.

    Google Scholar 

  11. F. W. Wang, R. E. Lowry, and W. H. Grant (1984). Novel excimer fluorescence method for monitoring polymerization: 1. Polymerization of methyl methacrylate. Polymer 25, 690.

    Google Scholar 

  12. F. W. Wang, R. E. Lowry, and B. M. Fanconi (1986). Novel fluorescence method for cure monitoring of epoxy resins. Polymer 27, 1529.

    Google Scholar 

  13. O. Valdes-Aquilera, C. P. Pathak, and D. C. Neckers (1990). Pyrene as a fluorescent probe for monitoring polymerization rates. Macromolecules 23, 689.

    Google Scholar 

  14. J. ączkowski and D. C. Neckers (1992). Developing fluorescence probe technology for monitoring the photochemibcal polymerization of polyolacrylates. Chemtracts-Macromol. Chem. 3, 75.

    Google Scholar 

  15. H. Morawetz (1989). Fluorescence studies of polymer dynamics. J. Luminesc. 43, 59.

    Google Scholar 

  16. W. F. Jager, D. Kudasheva, and D. C. Neckers (1996). Organic donor-Π-acceptor salts: A new type of probe for monitoring photopolymerization processes. Macromolecules 29, 7351-7355.

    Google Scholar 

  17. S. Wróblewski, K. Trzebiatowska, B. ędrzjewska, M. Pietrzak, R. Gawinecki, and J. Paczkowski (1999). Development of fluorescence probes based on stilbazolium salts for monitorin free radical polymerization processes. J. Chem. Soc., Perkin Trans. 2 1909-1917.

    Google Scholar 

  18. Ö. Pekcan, Y. Yilmaz, and O. Okay (1997). Real time monitoring of polymerization rate of methyl methacrylate using fluorescence probe. Polymer 38, 1693-1698.

    Google Scholar 

  19. K. Rotkiewicz, K. H. Grellman, and Z. R. Grabowski (1973). Reintepretation of the anomalous fluorescence of p-N,N-dimethylamino-benzonitrile. Chem. Phys. Lett. 19, 315-318.

    Google Scholar 

  20. Z. R. Grabowski, K. Rotkiewicz, A. Siemiarczuk, D. Cowley, and W. Baumann (1979). Twistrd intramolecular charge transfer states (TICT). A new class of excited states with a full charge separation. Nouv. J. Chim. 3, 443-454.

    Google Scholar 

  21. W. Rettig (1982). Intramolecular rotational relaxation of compounds which form “twisted intramolecular charge transfer” (TICT) excited states. J. Phys.Chem. 86, 1970-1976.

    Google Scholar 

  22. R. Hayashi, S. Tazuke, and C. W. Frank (1987). Twisted intramolecular charge-transfer phenomenon as a fluorescence probe of microenviroment. Effect of polymer concentration on lokal viscosity and microscopic polarity around a polymer chain of poly(methyl methacrylate). Macromolecules 20, 983-988.

    Google Scholar 

  23. A. Bajorek and J. ączkowski (1998). Influence of the attachment of chromophores to a polymer chain on their twisted intramolecular charge transfer state in dilute solution. Macromolecules 31, 86.

    Google Scholar 

  24. J. ączkowski and D. C. Neckers (1991). Twisted intramolecular charge transfer phenomenon as a quantitative probe of polymerization kinetics. Macromolecules 24, 3013-3016.

    Google Scholar 

  25. L. W. Jenneskens, H. J. Verhey, H. J. van Ramesdonk, A. J. Witteven, and J. W. Verhoeven (1992). Intramolecular charge transfer fluorescence of 1-phenyl-4-(4-cyano-1-naphthylmethylene)-piperidine in binary mixture of α,Ω-diacetylpoly(ethylene glycols) 1000 and 3000. Preferential solvation in the solid state. Macromolecules 25, 6365.

    Google Scholar 

  26. B. Strehmel, H. Seifert, and W. Rettig (1997). Photophysical properties of fluorescence probes. 2. A model of multiple fluorescence for stilbazolium dyes studied by global analysis and quantum chemical calculations. J. Phys. Chem. B. 101, 2232-2243.

    Google Scholar 

  27. B. Strehmel, M. Younes, V. Strehmel, and S. Wartewig (1992). Fluorescence probe studies during the curing of epoxy systems. Progr. Colloid Polym. Sci. 90, 1.

    Google Scholar 

  28. Gaussian 98 Revision A7: M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, and J. A. Pople.

  29. R. Gawinecki and K. Trzebiatowska (2001). Solvatochromism of 1-(p-aminostyryl)pyridinium salts. Polish J. Chem. 75, 231-239.

    Google Scholar 

  30. P. Fromherz and A. Heileman (1992). Twisted internal charge transfer in (aminophenyl)pyridinium. J. Phys. Chem. 96, 6864.

    Google Scholar 

  31. R. Foster (1969). Organic CT Complexes, Academic Press, London.

    Google Scholar 

  32. R. M. Hermant, N. A. C. Bakker, T. Scherer, B. Krijnen, and J. W. Verhoeven (1990). Systematic study of a series of highly fluorescent rod-shaped donor-acceptor systems. J. Am. Chem. Soc. 112(3), 1214.

    Google Scholar 

  33. R. A. Marcus (1989). Relation between charge transfer absorption and fluorescencespectra and the inverted region. J. Phys. Chem. 93, 3078and references cited therein.

    Google Scholar 

  34. J. Herbich and A. Kapturkiewicz (1998). Electronic structure and molecular conformation in the excited charge transfer singlet states of 9-acridyl and other aryl derivatives of aromatic amines. J. Am. Chem. Soc. 120, 1014.

    Google Scholar 

  35. A. Kapturkiewicz, J. Herbich, J. Karpiuk, and J. Nowacki (1997). Intramolecular radiative and radiationless charge recombination processes in donor-acceptor carbazole derivatives. J. Phys. Chem. A 101, 2332.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Faculty of Chemical Technology & Engineering, University of Technology & Agriculture, Seminaryjna 3, 85-326, Bydgoszcz, Poland

    Agnieszka Bajorek, Katarzyna Trzebiatowska, Beata Jędrzejewska, Marek Pietrzak, Ryszard Gawinecki & Jerzy Pączkowski

Authors
  1. Agnieszka Bajorek
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Katarzyna Trzebiatowska
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Beata Jędrzejewska
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Marek Pietrzak
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Ryszard Gawinecki
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Jerzy Pączkowski
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Jerzy Pączkowski.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Bajorek, A., Trzebiatowska, K., Jędrzejewska, B. et al. Developing of Fluorescence Probes Based on Stilbazolium Salts for Monitoring Free Radical Polymerization Processes. II. Journal of Fluorescence 14, 295–307 (2004). https://doi.org/10.1023/B:JOFL.0000024562.60225.d0

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/B:JOFL.0000024562.60225.d0

Search

Navigation