Synthesis, Absorption and Fluorescence Spectral Investigation of Phorphyrazines with Eight 2-Naphthalenecarboxy Esters

• Autorzy: Coskun N. Y. , Atak O. , Kiliçarslan F. A. , Yalçin S. M. , Gül A.
• Języki publikacji: EN

Abstrakty

EN

New magnesium porphyrazines substituted with eight naphthalenecarboxy groups on the peripheral positions were synthesized through a stepped reaction; first, cyclo tetramerization of 1,2-dicyano-1,2-bis(2-hydroxyethylthio)ethylene led to a porphyrazine formation which was subsequently esterified with 2-naphthoic acid. A metal-free derivative was prepared by treatment with trifluoroacetic acid. Metalloporphyrazines were prepared by insertion of Zn(II), Co(II) and Ni(II) ions. These porphyrazines were characterized by elemental analysis, 1H NMR, 13C NMR, LC-MS, FT-IR, and UV-Vis spectral data. In addition, fluorescence emissions of the compounds with naphthalene were obtained and the emissions due to the naphthalene moieties covalently-bonded to the porphyrazine were partially quenched.

Słowa kluczowe

EN

porphyrazine; fluorescence; naphthalene; zinc; cobalt; nickel; TGA

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2008
• Tom: Vol. 82, nr 11
• Strony: 2039--2047
• Opis fizyczny: Bibliogr. 33 poz., rys.

Twórcy

autor

Coskun N. Y.

autor

Atak O.

autor

Kiliçarslan F. A.

autor

Yalçin S. M.

autor

Gül A.

• 1Yildiz Technical University, Art and Science Faculty, Department of Chemistry, 34210 Esenler, Istanbul, Turkey,

Bibliografia

• 1. Miller J.S., Vazquez C., Calabrese J.C., McLean R.S. and Epstein A., J. Adv. Mater., 6, 217 (1994).
• 2. Morgan A.R., Peousis N.H. and Van Lier J.E., Eur J. Med Chem., 32, 21 (1997).
• 3. De Vos D.E. and Jacobs P.A., Catal Today, 57, 105 (2000).
• 4. VesperB.J., Lee S., Hammer N.D., Elseth K.M., Barrett A.G.M., Hoffman B.M. and Radosevich J.A.,J. Photochem. Photobiol B: Biology, 82, 180 (2006).
• 5. Salvati A., Ristori S., Pietrangeli D., Oberdisse J., Calamai L., Martini G. and Ricciardi G  Biophys Chem. 131, 43 (2007).
• 6. Kobayashi N., in: Porphyrin Handbook, Vol. 2, Kadish K.M., Smith K.M. Guilard R. (Eds.), Academic Press: San Diego (2000).
• 7. Freyer W., Mueller S. and Teuchner K., J. Photochem. Photobiol. A: Chemistry, 163, 231 (2004).
• 8. Freyer W., Neacsu C.C. and Raschke M.B., J. Luminescence, 128, 661 (2008).
• 9. Jiu T., Li Y., Gan H., Li Y, Liu H., Wang S., Zhou W., Wang C., Li X., Liu X. and Zhu D., Tetrahedron, 63, 232 (2003).
• 10. Duan X-F., Wang J-L. and Pei J., Org. Lett., 7(19), 4071 (2005).
• 11. Yilmaz M.D., Bozdemir O.A. and Akaya E.U., Org. Lett., 8(13), 2871 (2006).
• 12. Leng X., Choi C-F., Lo P-C. and Ng D.K.P., Org. Lett.t 9(2), 231 (2007).
• 13. Paul-Roth C.O. and Simonneaux G., C. R. Chimie, 9, 1277 (2006).
• 14. Barker C.A., Zeng X., Bettington S., Batsanov A.S., Bryce M.R. and Beeby A., Chem. Eur. J., 13,6710 (2007).
• 15. Paul-Roth C.O. and Simonneaux G., Tetrahedron Lett., 47, 3275 (2006).
• 16. Kuroda Y, Sugou K. and Sasaki K., J. Am. Chem. Soc., 122, 7833 (2000).
• 17. Sugou K., Sasaki K., Kitajima £., Iwaki T. and Kuroda Y, J. Am. Chem. Soc., 124(7), 1182 (2002).
• 18. Furutsu D., Satake A. and Kobuke Y, Inorg. Chem., 44(13), 4460 (2005).
• 19. Pispisa B., Venanzi M., Palleschi A. and Zanotti G., J. Photochem. Photobiol. A: Chemistry, 105(2-3),225 (1997).
• 20. Pispisa B., Stella L., Venanzi M., Palleschi A. and Zanotti G. Biopolymers, 54, 127 (2000).
• 21. Schramm C.J. and Hoffinan B.M., Inorg. Chem., 19,383 (1980).
• 22. Andersen K., Anderson M., Andersen O.P., Baum S., Baumann T.F., Beall L.S., Broderick W.E., Cook A.S., Eichhorn D.M., Goldberg D., Hope H., Jarrell W., Lange S. J., McCubbin Q.M., Mani N.S., Miller T., Montalban A.G., Rodrguez-Morgade M.S., Lee S., Nie H., Olmstead M.M., Sabat M., Sibert W.,Stern C., White A.J.P., Williams D.B.G., Williams D.J., Barrett A.G.M. and Hoffman B.M.,J. Heterocyclic Chem., 35, 1013 (1998).
• 23. Ricciardi G., Belviso S., Lelj F. and Ristori S., J. Porphyrins Phthalocyanines, 2, 177 (1998).
• 24. Ehrlich L.A., Skrdla P.J., Jarrell W.K., Sibert J.W, Armstrong N.R., Saavedra S.S., Barrett A.G.M. and Hoffman B.M., Inorg. Chem.. 39, 3963 (2000).
• 25. Lee S., White A.J.P., Williams D.J.,Barrettt A.G.M.and Hofman B.M.,J. Org. Chem.,66,461 (2001).
• 26. Deng K., Ding Z., Ellis D.E., Michel S.L.J. and Hoffinan B.M., Inorg. Chem., 40, 1110 (2001).
• 27. Lange S.J., Sibert J.W, Barrett A.G.M. and Hoffman B.M., Tetrahedron, 56, 7371 (2000).
• 28. Michel S.L.J., Barrett A.G.M. and Hoffman B.M., Inorg. Chem., 42(3), 814 (2003).
• 29. Prasad R. and Kumar A., Transit. Metal Chem., 2, 714 (2004).
• 30. Polat M. and Gul A., Dyes & Pigments, 45, 195 (2000).
• 31. Akkus H. and Gül A., Transit. Metal Chem., 26, 689 (2001).
• 32. Saglam Ö. and Gül A., Polyhedron, 20, 269 (2001).
• 33. Gońca E., Köseoglu Y., Akta § B. and Gül A., Polyhedron, 23, 1845 (2004).