Photosensitizing properties of the porphycene immobilized in sol-gel derived silica coating films

Tetrahedron Letters

Volumn 49, Issue 43, 2008, Pages 6198-6201

  Shimakoshi, Hisashi ^a   Baba, Tatsushi ^a   Iseki, Yusuke ^a   Endo, Ayataka ^a   Adachi, Chihaya ^a   Watanabe, Midori ^a   Hisaeda, Yoshio ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

Catalysis; Photosensitizer; Porphycene; Singlet oxygen; Sol gel method

Indexed keywords

GLASS; PORPHYCENE; PORPHYRIN; SILICA GEL; UNCLASSIFIED DRUG;

ARTICLE; CROSS-SECTIONAL STUDY; PHOTOGRAPHY AND FILM; PHOTOOXIDATION; PHOTOSENSITIZATION;

EID: 50949125100     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.08.003     Document Type: Article

References (39)

1. DeRosa M.C., and Crutchley R.J. Coord. Chem. Rev. 233-234 (2002) 351
2. Greer A. Acc. Chem. Res. 39 (2006) 797
3. Redmond R.W., and Gamlin J.N. Photochem. Photobiol. 70 (1999) 391
4. Bonnett R. Chem. Soc. Rev. 24 (1995) 19
5. Pandey R.K., and Zheng G. In: Kadish K.M., Smith K.M., and Guilard R. (Eds). The Porphyrin Handbook Vol. 6 (2000), Academic Press, New York 157
6. Pushpan S.K., Venkatraman S., Anand V.G., Sankar J., Parmeswaran D., Ganesan S., and Chandrashekar T.K. Curr. Med. Chem.-Anti-Cancer Agents 2 (2002) 187
7. Nyman E.S., and Hynninen P.H. J. Photochem. Photobiol., B 73 (2004) 1
8. Stockert J.C., Cañete M., Juarranz A., Horobin R.W., Borrell J., Teixidó I., and Nonell S. Curr. Med. Chem. 14 (2007) 997
9. Braslavsky S.E., Müller M., Mártire D.O., Pörting S., Bertolotti S.G., Chakravorti S., Koc-Weier G., Knipp B., and Schaffner K. J. Photochem. Photobiol., B 40 (1997) 191
10. Vogel E., Bröring M., Weghorn S.J., Scholz P., Deponte R., Lex J., Schmickler H., Schaffner K., Braslavsky S.E., Müller M., Pörting S., Fowler C.J., and Sessler J.L. Angew. Chem., Int. Ed. 36 (1997) 1651
11. Vogel E., Köcher M., Schmickler H., and Lex J. Angew. Chem., Int. Ed. Engl. 25 (1986) 257
12. Sánchez-García D., and Sessler J.L. Chem. Soc. Rev. 37 (2008) 215
13. Aramendia P.F., Redmond R.W., Santiago N., Schuster W., Braslavsky S.E., Schaffner K., and Vogel E. Photochem. Photobiol. 44 (1986) 555
14. Guardiano M., Biolo R., Jori G., and Schaffner K. Cancer Lett. 44 (1989) 1
15. Gottfried V., Davidi R., Averbuj C., and Kimel S. J. Photochem. Photobiol., B 30 (1995) 115
16. Villanueva A., Cañete M., Nonell S., Borrell J.I., Teixidó J., and Junarranz A. Anti-Cancer Drug Des. 11 (1996) 89
17. Fickweiler S., Abels C., Karrer S., Bäumler W., Landthaler M., Hofstädter, and Szeimies R.M. J. Photochem. Photobiol., B 48 (1999) 27
18. Polo L., Segalla A., Beroloni G., Jori G., Schaffner K., and Reddi E. J. Photochem. Photobiol., B 59 (2000) 152
19. Baumer D., Maier M., Engl R., Szeimies R.M., and Bäumler W. Chem. Phys. 285 (2002) 309
20. Mak N.-K., Kok T.-W., Wong R.-N.-S., Lam S.-W., Lau Y.-K., Leung W.-N., Cheung N.-H., Huang D.P., Yeung L.-L., and Chang C.K. J. Biomed. Sci. 10 (2003) 418
21. Schere K., Abels C., Baumler W., Ackermann G., and Szeimies R.M. Arch. Dematol. Res. 295 (2004) 535
22. Kessel D., Conley M., Vicente M.G.H., and Reiners Jr. J.J. Photochem. Photobiol. 81 (2005) 569
23. Baba T., Shimakoshi H., and Hisaeda Y. Tetrahedron Lett. 45 (2004) 5973
24. Baba T., Shimakoshi H., Endo A., Adachi C., and Hisaeda Y. Chem. Lett. 37 (2008) 264
25. Shimakoshi H., Baba T., Iseki Y., Endo A., Adachi C., and Hisaeda Y. Chem. Commun. (2008) 2882
26. Arnbjerg J., Jiménez-Banzo A., Paterson M.J., Nonell S., Borrell J., Christiansen O., and Ogilby P.R. J. Am. Chem. Soc. 129 (2007) 5188
27. Gladysz J.A. Ed. Chem. Rev. 102 (2002) 3215 special issue
28. Shimakoshi H., Nakazato A., Tokunaga M., Katagiri K., Ariga K., Kikuchi J., and Hisaeda Y. Dalton Trans. (2003) 2308
29. +, 762.4089.
30. 2 aqueous solution for 30 min followed by sonication in ethanol for 1 h at 303 K, and then dried with nitrogen gas.
31. The sol-gel solution (10 μL) was placed on the glass substrate and spun at 500 rpm for 10 s (1st) and then 2000 rpm for 10 s (2nd).
32. f value was measured using an absolute photoluminescence quantum efficiency measurement system (Hamamatsu C9920-02) incorporating an integrating sphere. The gel film was deposited on a mica substrate.
33. 2 in air at room temperature with a 500 W tungsten lamp (TOSHIBA Y-46 filter, λ > 460 nm).
34. 3OH (9:1, v/v) in air at room temperature with a 500 W tungsten lamp (TOSHIBA Y-46 filter, λ > 460 nm).
35. Suchard O., Kane R., Roe B.J., Zimmermann E., Jung C., Waske P.A., Mattay J., and Oelgemöller M. Tetrahedron 62 (2006) 1467
36. 3, 500 MHz): δ = 6.94 (s, 2H), 7.27 (dd, 1H, Ph), 7.60- 7.65 (m, 2H, Ph), 11.90 (s, 1H, OH).
37. The intensity of the UV-vis absorption at 651 nm of the gel film was monitored during every run.
38. 3OH (9:1, v/v) in air at room temperature with a 500 W tungsten lamp (TOSHIBA Y-46 filter, λ > 460 nm).
39. 3, 500 MHz): δ = 6.96 (s, 2H), 7.74 (m, 2H, Ph), 8.06 (m, 2H, Ph).