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Technical Issues
1/2015 pp. 47-53

Pochodne kumaryny jako molekularne sensory fluorescencyjne stosowane do monitorowania procesów fotopolimeryzacji

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This paper presents research on the use of coumarin derivatives as fluorescent molecular probes for monitoring cationic and free radical photopolymerization processes, using for that purpose modern FPT method (Fluorescence Probe Technology). Literature review on the main trends of applications and spectroscopic properties of coumarin derivatives was described. In the following part of publication, relations between change of fluorescence characteristic and physicochemical changes occurring in the polymerizable composition, (both microviscosity and polarity) were explained. This article also presented the basic methodology of studies on the control of the photopolymerization reaction on-line and off-line, using fluorescence spectroscopy and parameters such as: fluorescence intensity ratio R, number of progress of the reaction β and molecular probe sensitivity S.

Key words

fluorescence probes; cationic photopolymerization; radical photopolymerization; coumarin derivatives; FPT; polymerization processes monitoring


1. Lacy, A., O’Kennedy, R., Studies on coumarins and coumarin-related compounds to determine their therapeutic role in the treatment of cancer, Curr. Pharm. Design, 2004, 10, pp. 3797-3811.

2. Majumder, P.L., Majumder, S., Synthesis of novel coumarin derivatives and its biological evaluation, Eur. J. Med. Chem., 1993, 28, pp. 572-578.

3. Weiss, P., Photo-induced polymerization, Pure Appl. Chem., 1967, 15, pp. 587-600.

4. Shaabani, A., Ghadari, R., Rahmati, A., Rezayan A.H., Coumarin synthesis via Knoevenagel condensation reaction in 1,1,3,3-N,N,N’,N’-tetramethylguanidiniumtrifluoroacetate ionic liquid, J. Iran chem. Soc., 2009, 6(4), pp. 710-714.

5. Upadhyay, K.K., Mishra, R.K., Kumar, A., A convenient synthesis of some coumarin derivatives using SnCl2.2H2O as catalyst, Catal. Lett., 2008, 121, pp. 118-12.

6. Harayama, T., Nakatsuka, K., Nishioka, H., Murakami, K., Hayashida, N., Ishii, H., Convenient synthesis of a simple coumarin from salicyaldehyde and Witting reagent. II: Synthesis of bromo- and (methylcarbonyl) coumarin, Chem. Pharm. Bull, 1994, 42(10), pp. 2170-2173.

7. Braz, J., Photophysical properties of coumarin compounds in neat and binary solvent mixtures: evaluation and correlation between solvatochromism and solvent polarity parameters, Chem. Soc., 2014, 25, 5, pp. 873-88.

8. Li, H., Cai, L., Chen, Z., Coumarin-derived fluorescent chemosensors, Anal. Lett., 2008, 41, pp. 2203-2213.

9. Sahoo, S.S., Shukla, S., Nandy, S., Sahoo, H.B., Synthesis of novel coumarin derivatives and its biological evaluations, Eur. J. Exp. Biol., 2012, 2 (4), pp. 899-908.

10. Morris, J.C., McMurtrie, J.C., Bottle, S.E., Fairfull-Smith, K.E., Generation of profluorescent isoindoline nitroxides Using Click Chemistry, J. Org. Chem., 2011,17;76(12), pp. 4964‑72.

11. Ortyl, J., Popielarz, R., FPT-Fluorescent Probe Technology – innowacyjna technologia monitoringu fotopolimeryzacji w przemyśle powłok polimerowych, [w:] Nauka i przemysł–Wyzwania i bariery, Wydawnictwo Uczelniane PK, Kraków 2009, s. 139-152. ISBN 978-83-7242-516-4.

12. Mattoo, B. N., Absorption and fluorescence spectra of coumarins, Trans. Faraday Soc., 1956, 52, pp. 1184‑1194.

13. Wagner, B., The Use of Coumarins as Environmentally-Sensitive Fluorescent Probes of Heterogenous Inclusion Systems, Molecules, 2009, 14, pp. 210-237.

14. Ortyl, J., Sawicz, K., Popielarz, R., Performance of Aminocoumarins as Probes for Monitoring of Cationic Photopolymerization of Monomers by Fluorescence Probe Technology, J. Polym. Sci., Part A: Polym. Chem, 2010, 48, pp. 4522-4528.

15. Ortyl, J., Sawicz, K., Popielarz, R., Nowe sondy fluorescencyjne do monitorowania procesu utwardzania żywic epoksydowych, Czasopismo Techniczne, Ser. Chemia, 1‑Ch/2009, s. 119-126.

16. Ortyl J., Popielarz R., Technologia sond fluorescencyjnych (Fluorescence Probe Technology) do badań procesów fotopolimeryzacji, VI Krakowska Konferencja Młodych Uczonych, Kraków, 2011.

17. Sawicz-Kryniger, K., Technika sond fluorescencyjnych do monitorowania procesów sieciowania kompozycji epoksydowych, praca doktorska, Politechnika Krakowska, 2013.