New Photosensitive Methacrylate Monomers with 4-Aminoazobenzene Type Chromophore Group

• Autorzy: Janik R. , Kucharski S. , Kubaińska A. , Łyko B.
• Języki publikacji: EN

Abstrakty

EN

Photosensitive methacrylate monomers, derivatives of azobenzene, were synthesized. The route of syntheses was based on coupling of diazonium salts of sulfathiazole, sulfomethoxazole, sulfadiazine, 4-aminobenzoic acid and 4-nitroaniline with N-alkyl-N- [2-(methacryloyloxy)ethyl]aniline. The trans cis isomerization of the monomers in DMSO solution was investigated by UV-VIS spectroscopy recording their spectra during illumination and thermal recovery periods. It was found that except for nitro derivatives the yield of trans-cis isomerization was ca. 50% and that the reverse reaction was a result of thermal relaxation. The spectroscopic studies were accompanied by quantum chemical calculations.

Słowa kluczowe

EN

4-aminoazobenzene derivaties; methacrylate monomers; NLO-phores; E-Z; Z-E isomerization; quantum chemical calculation

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2001
• Tom: Vol. 75, nr 2
• Strony: 241--252
• Opis fizyczny: Bibliogr. 31 poz., rys.

Twórcy

autor

Janik R.

• Institute of Organic and Polymer Technology, Wrocław University of Technology, ul. Wyspianskiego 27, 50-370 Wrocław, Poland

autor

Kucharski S.

• Institute of Organic and Polymer Technology, Wrocław University of Technology, ul. Wyspianskiego 27, 50-370 Wrocław, Poland

autor

Kubaińska A.

• Institute of Organic and Polymer Technology, Wrocław University of Technology, ul. Wyspianskiego 27, 50-370 Wrocław, Poland

autor

Łyko B.

• Institute of Organic and Polymer Technology, Wrocław University of Technology, ul. Wyspianskiego 27, 50-370 Wrocław, Poland

Bibliografia

• 1. Nalwa H.S. and Miyata S., Eds., Nonlinear Optics of Organic Molecules and Polymers, CRC Press, Boca Raton-NY-London-Tokyo, 1997.
• 2. Rau H., In Photochemistry and Photophysics, Rabek F.J., Ed., CRC, Boca Raton, FL, 1990, Vol. II, Chapter 4, pp. 119-141.
• 3. BurIand D.M., Miller R.D. and Walsh C.A., Chem. Rev., 94, 31 (1994).
• 4. Moemer W.E. and Silence S.M., Chem, Rev., 94, 127 (1994).
• 5. Lindsay G.A. and Singer K.D., Eds., Polymers for Second-Order Nonlinear Optics, ACS Symposium Series 601, ACS, Washington, DC, 1995.
• 6. Jenekhe S.A. and Wynne K.J., Eds., Photonic and Optoelectronic Polymers, ACS Symposium Series 672, ACS, Washington, DC, 1995.
• 7. Barley S.FL, Gilbert A. and Mitchell G.R., J. Mater. Chem., 1, 481 (1991).
• 8. Natansohn A., Rochon P., Gosselin J. and Xie S., Macromol., 25, 2268 (1992).
• 9. Ruhmann R., Zschuppe V., Dittmer M. and Wolff D., Makromol. Chem., 193, 3073 (1992).
• 10. Czapla S., Ruhmann R., Rtibner J., Zschuppe V. and Wolff D., Makromol. Chem., 194, 243 (1993).
• 11. Haitjema H.J., von Morgen G.L., Tan Y.Y. and Challa G., Macromol, 27, 6201 (1994).
• 12. Natansohn A., Rochon P., Pezolet M., Audet P., Brown D. and To S., Macromol, 27, 2580 (1994).
• 13. Xie S., Natansohn A. and Rochon P., Macromol., 27, 1885 (1994).
• 14. Brown D., Natansohn A. and Rochon P., Macromol, 28, 6116 (1995).
• 15. Ho M.S., Natansohn A. and Rochon P., Macromol., 28, 6124 (1995).
• 16. Morino S., Machida S., Yamashita T. and Horie K., J. Phys. Chem., 99, 10280 (1995).
• 17. Cross E.M., White K.M., Moshrefzadeh R.S. and Francis C.V., Macromol., 28, 2526 (1995).
• 18. Haitjema H.J., Buruma R., Alberda van Ekenstein G.O.R., Tan Y.Y. and Challa G., Eur. Polym. J., 32, 1447(1996).
• 19. Meng X., Natansohn A., Barrett C. and Rochon P., Macromol., 29, 946 (1996).
• 20. Ho M.S., BarrettC., Paterson J., Esteghamatian M., Natansohn A. and Rochon P., Macromol., 29, 4613 (1996).
• 21. Stumpe J., Lasker L., Fischer Th., Rutloh M,, Kostromin S. and Ruhmann R., Thin Solid Films, 284-285, 252,(1996).
• 22. Barrett C., Choudhury B., Natansohn A. and Rochon P., Macromol., 31, 4845 (1998).
• 23. Springer J., Leitner M.B. and Ruhmann R., Polimery, 44, 13 (1999).
• 24. Altomare A., Andruzzi L., Ciardeili F., Solaro R. and Tirelli N„ Macromol. Chem. Phys., 200, 601 (1999).
• 25. Haitjema H.J., Buruma R., Alberda van Ekenstein G.O.R., Tan Y.Y. and Challa G., Eur. Polym. J., 32, 1437 (1996).
• 26. Frish M.J.,Tracks G.W., Schlcgel H.B., Gill P.M.W., Johnson B.G., Robb M.A., Cheeseman J.R., Keith T., Petersson G.A., Montgomery J.A., Raghavachari K., Al.-Laham M.A., Zakrzewski V.G., Ortiz J.V., Foresman J.B., Cioslowski J., Stefanow B.B., Nanayakkara A., Chaltacombe M., Peng C.Y., Ayala P.Y., Chen W., Wong M.W., Andres J.L., Replogle E.S., Gomperts R., Martin R.L., Fox D.J., Binkley J.S., Defrees D.J., Baker J., Stewart J.P., Head-Gordon M., Gonzalez C. and Pople J.A., Gaussian, 94, Revision D.3; Gaussian, Inc.: Pittsburgh, PA, 1994.
• 27. Thomson M.A. and Zemer M.C., J. Am. Chem. Soc,, 112, 7828 (1990); 113, 8210 (1991).
• 28. Thomson M.A., Zemer M.C. and Fajer J., J. Phys. Chem., 95, 5693 (1991).
• 29. Janik R. and Kucharski S., RP Patent Appl., P-334643, 1999.
• 30. King N.R., Whale A.E., Davis F.J., Gilbert A. and Mitchell G.R., J. Mater. Chem., 7, 625 (1997).
• 31. Kucharski S., Janik R., Motschmann H. and Radiige C., New J. Chem., 23, 765 (1999).