Photophysical properties of neutral and cationic tetrapyridinoporphyrazines

Photochemistry and Photobiology

Volumn 71, Issue 1, 2000, Pages 53-59

  Martí, Cristina ^a   Nonell, Santi ^a   Nicolau, Mónica ^b   Torres, Tomás ^a,b  

^a INSTITUT QUÍMIC DE SARRIÀ   (Spain)

^b UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CATION; MONOMER; NITROGEN; OZONE; PHOTOSENSITIZING AGENT; PHTHALOCYANINE DERIVATIVE; SINGLET OXYGEN; TETRAPYRIDINOPORPHYRAZINE; UNCLASSIFIED DRUG;

ABSORPTION; ALKYLATION; AQUEOUS SOLUTION; ARTICLE; ATOMIC PARTICLE; DRUG SYNTHESIS; FLUORESCENCE; PHOTODYNAMICS;

EID: 0033993330     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1562/0031-8655(2000)0710053PPONAC2.0.CO2     Document Type: Article

References (35)

1. Sternberg, E. D., D. Dolphin and C. Brückner (1998) Porphyrin-based photosensitizers for use in photodynamic therapy. Tetrahedron 54, 4151-4202.
2. Malik, Z., J. Hanania and Y. Nitzan (1990) Bactericidal effects of photoactivated porphyrins. An alternative approach to antimicrobial drugs. J. Photochem. Photobiol. B Biol. 5, 281-293.
3. Merchat, M., G. Bertolini, P. Giacomini, A. Villanueva and G. Jori (1996) Meso-substituted porphyrins as efficient photosensitizers of Gram-positive and Gram-negative bacteria. J. Photochem. Photobiol. B Biol. 32, 153-157.
4. Nitzan, Y., M. Gutterman, Z. Malik and B. Ehrenberg (1992) Inactivation of Gram-negative bacteria by photosensitized porphyrins. Photochem. Photobiol. 55, 89-96.
5. Minnock, A., D.I. Vernon, J. Schofield, J. Griffiths, J.H. Parish and S.B. Brown (1996) Photoinactivation of bacteria. Use of a cationic water-soluble zinc phthalocyanine to photoinactivate both Gram-negative and Gram-positive bacteria. J. Photochem. Photobiol. B Biol. 32, 159-164.
6. Wöhrle, D., J. Gitzel, I. Okura and S. Aono (1985) Photoredox properties of tetra-2,3-pyridinoporphyrazines (29H, 31H-tetrapyrido(2,3-b:2′,3′-g:2″;,3″-l:2‴, 3‴ '-q)porphyrazine). J. Chem. Soc. Perkin Trans II, 1171-1178.
7. Cabezón, B., S. Rodríguez-Morgade and T. Torres (1995) Stepwise synthesis of soluble substituted triazolephthalocyanines. J. Org. Chem. 60, 1872-1874.
8. Fernández-Lázaro, F., T. Torres, B. Hauschel and M. Hanack (1998) Hemiporphyrazines as targets for the preparation of molecular materials: synthesis and physical properties. Chem. Rev. 98, 563-575.
9. Palacin, S. and A. Barraud (1989) Highly ordered langmuir-Blodgett films based on semi-amphiphilic phthalocyanines. J. Chem. Soc., Chem. Commun. 45-47.
10. Kobayashi, N. (1993) Synthesis and spectroscopic properties of phthalocyanine analogues. Phthalocyanines. Properties and applications. Volume 2, (Edited by C. Leznoff and A.B.P. Lever), pp. 97-161
11. Kudrevich, S.V. and J.E. Van Lier (1996) Azaanalogs of phthalocyanine: synthesis and properties. Coord. Chem. Rev. 156, 163-182.
12. Porteu, F., S. Palacin, A. Raudel-Teixier and A. Barraud (1991) Supermolecular engineering at the air-water interface: spatially controlled formation of heterodimers from amphiphilic porphyrins and porphyrazines through specific molecular recognition. J. Phys. Chem. 95, 7438-7447.
13. Scott, J. E. (1970) Histochemistry of alcian blue. I. metachromasia of alcian blue, astrablau and other cationic phthalocyanine dyes. Histochemie 21, 277-285.
14. Carniato, S., H. Roulet, G. Dufour, S. Palacin, A. Barraud, P. Millié and I. Nenner (1992) Electronic structure of nitrogen square planar copper complexes in Langmuir-Blodgett films. J. Phys. Chem. 96, 7072-7075.
15. Palacin, S., A. Ruaudel-Teixer and A. Barraud (1986) Chemical reactivity in monolayers: study of amphiphilic tetrapyridinoporphyrazine in Langmuir-Blodgett films. J. Phys. Chem. 90, 6237-6242.
16. Palacin, S., A. Ruaudel-Teixer and A. Barraud (1989) Molecular engineering: highly ordered Langmuir-Blodgett films based on a cobalt phthalocyanine and its axial complexation. J. Phys. Chem. 93, 7195-7199.
17. Nicolau, M., G. Rojo, T. Torres, F. Agulló-López (1999) Synthesis and third-harmonic generation in thin films of tetrapyridinoporphyrazines: effect of molecular aggregation. J. Porphyrins Phthalocyanines 3, in press.
18. Nonell, S., M. González and F.R. Trull (1993) 1H-Phenalen-1-one-2-sulfonic acid: an extremely efficient singlet molecular oxygen sensitizer for aqueous media. Afinidad 50, 445-450.
19. Fouriaux, S., F. Armand, O. Araspin, A. Ruaudel-Teixier, E. Maya, P. Vázquez and T. Torres (1996) Effect of the metal on the organization of tetraamidometallophthalocyanines in Langmuir-Blodgett Films. J. Phys. Chem. 100, 16984-16988.
20. Darwent, J. R., P. Douglas, A. Harriman, G. Porter and M.C. Richoux (1982) Metal phthalocyanines and porphyrins as photosensitizers for reduction of water to hydrogen. Coord. Chem. Rev. 44, 83-126.
21. Hildenbrand, K. and C. Nicolau (1979) Nanosecond fluorescence anisotropy decays of 1,6-diphenyl-1,3,5-hexatriene in membranes. Biochim. Biophys. Acta 553, 365-377.
22. g) photosensitization, time-resolved photoacoustic and NIR emission studies. J. Photochem. Photobiol. A:Chem. 97, 11-18.
23. Braslavsky, S.E. and G.E. Heibel (1992) Time-resolved photothermal and photoacoustic methods applied to photoinduced processes in solution. Chem. Rev. 92, 1381-1410.
24. n, where M = Si, Ge, and Sn. J. Am. Chem. Soc. 105, 1539-1550.
25. Lowery, M. K., A.J. Starkshack, J.N. Esposito, P.C. Krueger and M.E. Kenney (1965) Dichloro(phthalocyanino)silicon. Inorg. Chem. 4, 128.
26. Sielcken, O. E., L.A. Van de Kuil, W. Drenth, J. Schooman and R.J.M. Nolte (1990) Phthalocyaninato polysiloxanes substituted with crown ether moieties. J. Am. Chem. Soc. 112, 3086-3093.
27. Ciliberto, E., K.A. Doris, W.J. Pietro, G.M. Reisner, D.E. Ellis, I. Fragalà, F.H. Herbstein, M.A. Ratner and T.J. Marks (1984) π-π Interactions and bandwidths in "Molecular Metals." A chemical, structural, photoelectron spectroscopic, and Hartree-Fock-Slater study of monomeric and cofacially joined dimeric silicon phthalocyanines. J. Am. Chem. Soc. 106, 7748-7761.
28. Kane, A.R., J.F. Sullivan, D.H. Kenny and M.E. Kenney (1970) The nuclear magnetic resonance spectra and the electronic spectra of some silicon and germanium phthalocyanines. Inorg. Chem. 9, 1445-1448.
29. Katayose, M., S. Tai, F. Kampas, K. Kamijima, H. Hagiwara and N. Hayashi (1992) Novel silicon naphthalocyanines: synthesis and molecular arrangement in thin films. J. Chem. Soc. Perkin Trans. II. 403-409.
30. Tai, S., N. Hayashi, K. Kamijima, M. Katayose, T. Akimoto and H. Hagiwara (1999) Tetraazaporphine for optical recording material. Patent EP 0 344 891 A2 (113:201457 CA).
31. Cook M.J. and J. Jafari-Fini (1997) Pyridino (3,4) tribenzoporphyrazines: edge-to-face versus face-to-face assemblies among phthalocyanine analogues. J. Mater. Chem., 7 (12), 2327-2329.
32. Jacques, P. and A.M. Braun (1981) Laser flash photolysis of phthalocyanines in solution and microemulsion. Helv. Chim. Acta 64, 1800-1806.
33. Oliveros, E., P.S. Murasecco, T.A. Saghafi, A.M. Braun and H.J. Hansen (1991) 1 H-Phenalen-1-one: Photophysical properties and singlet-oxygen production. Helv. Chim. Acta 74, 79-90.
34. g) sensitization. J. Photochem. Photobiol. A:Chem. 79, 11-17.
35. Wilkinson, F., W.P. Helman and A.B. Ross (1993) Quantum yields for the photosensitized formation of the lowest electronically excited singlet state of molecular oxygen in solution. J. Phys. Chem. Ref. Data 22, 113-262.