Synthesis and Some Properties of Phosphonomethyl Substituted Phthalocyanines

Alexey N. Komissarov, Dmitry A. Makarov, Olga A. Yuzhakova,
Lubov P. Savvina, Nina A. Kuznetsova, Oleg L. Kaliya, Evgeny А. Lukyanets, and
Vladimir M. Negrimovsky^@

State Research Center “Organic Intermediates and Dyes Institute” (SRC “NIOPIK”), 123995 Moscow, Russia

^@Corresponding author E-mail: vnegrimovsky@mail.ru

Macroheterocycles 2012 5(2) 169-174

DOI: 10.6060/mhc2012.120466n

A new method of synthesis of phthalocyanines with phosphonate moieties is developed; significant dependence of their spectral, photochemical and photophysical properties on pH value was found.

mhc2012_t05n2_169-174.pdf (785.03 KB)

References:

Click here to expand or collapse this section

1. Erk P., Hengelsberg H., Phthalocyanine dyes and pigments / In The Porphyrin Handbook (Karl M. Kadish, Kevin M. Smith (Eds.)), Vol. 19, Academic press: 2002, p. 105.

2. Kaliya O.L., Lukyanets E.A., Vorozhtsov G.N. J. Porphyrins Phthalocyanines, 1999, 3, p. 592.
http://dx.doi.org/10.1002/(SICI)1099-1409(199908/10)3:6/7<592::AID-JPP180>3.0.CO;2-G

3. Torre G., Vazquez P., Agullo-Lopez F., Torres T. Chem. Rev., 2004, 104, p. 3723.
http://dx.doi.org/10.1021/cr030206t

4. Vilakazi S., Nyokong T. Polyhedron, 2000, 19, p. 229.
http://dx.doi.org/10.1016/S0277-5387(99)00373-3

5. Walter M., Rudine A., Wamser. C. J. Porphyrins Phthalocyanines., 2010, 14, p. 759.
http://dx.doi.org/10.1142/S1088424610002689

6. Imahori H., Umeyama T., Ito S. Accounts of Chem. Res., 2009, 42, N 11, p. 1809.
http://dx.doi.org/10.1021/ar900034t

7. Werner F., Gnichwitz J., Marczak R., Palomares E., Peukert W., Hirsch A., Guldi D. J. Phys. Chem., B 2010, 114, p. 14671.
http://dx.doi.org/10.1021/jp102737a

8. Pechy P., Rotzinger F.P., Nazeeruddin M.K., Kohle O., Zakeeruddin S.M., Humpry-Baker R., Gratzel M. J. Chem. Soc., Chem. Commun., 1995, p. 65.
http://dx.doi.org/10.1039/C39950000065

9. Ardo S., Meyer G. Chem. Soc. Rev., 2009, 38, p. 115.
http://dx.doi.org/10.1039/b804321n

10. Lukyanets E.A. J. Porphyrins Phthalocyanines, 1999, 3, p. 424.
http://dx.doi.org/10.1002/(SICI)1099-1409(199908/10)3:6/7<424::AID-JPP151>3.0.CO;2-K

11. Nyman E.S., Hynninen P.H. J. Photochem. Photobiol. B: Biol., 2004, 73, p. 1.
http://dx.doi.org/10.1016/j.jphotobiol.2003.10.002

12. Meerovich G.A., Lukyanets E.A., Yuzhakova O.A., Torshina N.L., Loschenov V.B., Stratonnikov A.A., Kogan E.A., Vorozhtsov G.N., Kunets A.V., Kuvshinov Y.P., Poddubny B.K., Volkova A.I., Posypanova A.M. Proc. SPIE, 1997, 2924, p. 86.
http://dx.doi.org/10.1117/12.260769

13. Yuzhakova O.A., Kuznetsova N.A., Lukyanets E.A., Negrimovsky V.M. Patent RU 2405785 (2009).

14. Lukyanets E.A., Negrimovsky V.M., Yuzhakova O.A. et.al. Patent RU 2164136 (1998).

15. Kuznetsova N., Gretsova N., Yuzhakova O., Negrimovsky V., Kaliya O., Lukyanets E. Rus. J. Gen. Chem., 2001, 71, p. 36.
http://dx.doi.org/10.1023/A:1012369120376

16. Postovsky Yu., Bednyagina N. Zh. Org. Khim., 1937, 7, p. 2919.

17. Gelman N.E., Terent’eva E.A., Shanina T.M., Kiparenko L.M. Metody kolichestvennogo organichesogo elementnogo mikroanaliza [Methods of quantitative organic elemental microanalysis]. 1987. Moskva: “Khimiya”, 296 p. (in Russ.).

18. Ogunsipe A., Chen Ji Y., Nyokong T. New J. Chem, 2004, 28, p. 822.
http://dx.doi.org/10.1039/b315319c

19. Kuznetsova N.A., Gretsova NS, Derkacheva VM et al. J. Porphyrins Phthalocyanines, 2003, 7, p. 147.
http://dx.doi.org/10.1142/S1088424603000203

20. Vorozhtsov G.N., Kogan E.A., Loshchenov V.B. et al. Patent RU 2146144 (1997).

21. Ciliberto E., Doris K.A., Pietro W.J., Reisner G.M., Ellis D.E. J. Am. Chem. Soc., 1984, 106, p. 7748.
http://dx.doi.org/10.1021/ja00337a018

22. Nyokong T. Coordination Chemistry Reviews, 2007, 251, p. 1707.
http://dx.doi.org/10.1016/j.ccr.2006.11.011

23. Kuznetsova N., Makarov D., Yuzhakova O., Strizhakov A., Roumbal Y., Ulanova L., Krasnovsky A., Kaliya O. Photochem. Photobiol. Sci., 2009, 8, p. 1724.
http://dx.doi.org/10.1039/b9pp00054b

24. Slota R., Dyrda G. Inorg. Chem., 2003, 42, p. 5743.
http://dx.doi.org/10.1021/ic0260217

25. Ferraudi G. Photochemical properties of Metallophthalocyanines in Homogeneous Solution / In: Phthalocyanines. Properties and Applications (C.C. Leznoff, A.B.P. Lever (Eds.)), Vol. 1, New York: VCH. 1989. p. 291-340.

26. Egorov S.Y., Kamalov V.F., Koroteev N.I., Krasnovsky A.A., Toleutaev B.N., Zinukov S.V. Chem. Phys. Lett., 1989, 163, p. 421.
http://dx.doi.org/10.1016/0009-2614(89)85161-9

27. Ogilby P.R., Foote C.S. J. Am. Chem. Soc., 1982, 104, p. 2069.
http://dx.doi.org/10.1021/ja00371a067

28. Kuznetsova N., Gretsova N., Derkacheva V., Mikhalenko S., Solov’eva L., Yuzhakova O., Kaliya O., Lukyanets E., Rus. J. Gen. Chem., 2002, 72, p. 300.
http://dx.doi.org/10.1023/A:1015402524813

Attachment	Size
mhc2012_t05n2_169-174.pdf	785.03 KB

Журнал "Макрогетероциклы"

Navigation

Languages

News

Search