Photophysical Properties of Neutral and Cationic Tetrapyridinoporphyrazines
Cristina Martí
Institut Químic de Sarrià, Universitat Ramon Llull, Barcelona, Spain
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Santi Nonell
Institut Químic de Sarrià, Universitat Ramon Llull, Barcelona, Spain
*To whom correspondence should be addressed at: Institut Químic de Sarrià, Universitat Ramon Llull, Via Augusta, 390, E-08017 Barcelona (Spain); [email protected]Search for more papers by this authorMónica Nicolau
Dpto. Química Orgánica C-I. Universidad Autónoma de Madrid, Cantoblanco, Madrid, Spain
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Tomás Torres
Dpto. Química Orgánica C-I. Universidad Autónoma de Madrid, Cantoblanco, Madrid, Spain
*To whom correspondence should be addressed at: Institut Químic de Sarrià, Universitat Ramon Llull, Via Augusta, 390, E-08017 Barcelona (Spain); [email protected]Search for more papers by this authorCristina Martí
Institut Químic de Sarrià, Universitat Ramon Llull, Barcelona, Spain
Search for more papers by this authorCorresponding Author
Santi Nonell
Institut Químic de Sarrià, Universitat Ramon Llull, Barcelona, Spain
*To whom correspondence should be addressed at: Institut Químic de Sarrià, Universitat Ramon Llull, Via Augusta, 390, E-08017 Barcelona (Spain); [email protected]Search for more papers by this authorMónica Nicolau
Dpto. Química Orgánica C-I. Universidad Autónoma de Madrid, Cantoblanco, Madrid, Spain
Search for more papers by this authorCorresponding Author
Tomás Torres
Dpto. Química Orgánica C-I. Universidad Autónoma de Madrid, Cantoblanco, Madrid, Spain
*To whom correspondence should be addressed at: Institut Químic de Sarrià, Universitat Ramon Llull, Via Augusta, 390, E-08017 Barcelona (Spain); [email protected]Search for more papers by this authorABSTRACT
We describe the synthesis and photophysical properties of a series of neutral and cationic 3,4-tetrapyridinoporphyrazines, potential lead photosensitizers for photodynamic inactivation of bacteria. Tetracationic TPyPzs exist essentially as monomers in aqueous systems, but the presence of trialkylated compounds due to incomplete quaternization of the outer nitrogen atoms induces severe aggregation. The absorption, fluorescence, triplet, and singlet oxygen quantum yields for both the neutral and cationic compounds are comparable to those of the related phthalocyanines.
REFERENCES
- 1 Sternberg, E. D., D. Dolphin, C. Brückner (1998) Porphyrin-based photosensitizers for use in photodynamic therapy. Tetrahedron, 54, 4151–4202.
- 2 Malik, Z., J. Hanania, 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, 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, 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, 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, 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, T. Torres (1995) Stepwise synthesis of soluble substituted triazolephthalocyanines. J. Org. Chem, 60, 1872–1874.
- 8 Fernández-Lázaro, F., T. Torres, B. Hauschel, M. Hanack (1998) Hemiporphyrazines as targets for the preparation of molecular materials: synthesis and physical properties. Chem. Rev, 98, 563–575.
- 9 Palacin, S., 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., 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, 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, 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, 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, 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, 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, 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, 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., C. Nicolau (1979) Nanosecond fluorescence anisotropy decays of 1,6-diphenyl-1,3,5-hexatriene in membranes. Biochim. Biophys. Acta, 553, 365–377.
- 22 Martí, C., O. Jürgens, O. Cuenca, M. Casals, S. Nonell (1996) Aromatic ketones as standards for singlet molecular oxygen O2(1Δg) photosensitization. time-resolved photoacoustic and NIR emission studies. J. Photochem. Photobiol. A:Chem, 97, 11–18.
- 23 Braslavsky, S.E., G.E. Heibel (1992) Time-resolved photothermal and photoacoustic methods applied to photoinduced processes in solution. Chem. Rev, 92, 1381–1410.
- 24 Dirk, C. W., T. Inabe, K.F.J. Schoch, T.J. Marks (1983) Cofacial assembly of partially oxidized metallomacrocycles as an approach to controlling lattice architecture in low-dimensional molecular solids. Chemical and architectural properties of the “face-to-face” polymers (M(phthalocyaninato)O)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, M.E. Kenney 1965 Dichloro(phthalocyanino)silicon Inorg. Chem 4 128
- 26 Sielcken, O. E., L.A. Van de Kuil, W. Drenth, J. Schooman, 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, 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, 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, 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, H. Hagiwara 1999 Tetraazaporphine for optical recording material Patent EP 0 344 891 A2 (113:201457 CA)
- 31 Cook, M.J., J. Jafari-Fini (1997) Pyridino (3,4) tribenzoporphyrazines: edge-to-face versus face-to-face assemblies among phthalocyanine analogues. J. Mater. Chem., 712), 2327–2329.
- 32 Jacques, P., 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, H.J. Hansen (1991) 1 H-Phenalen-1-one: Photophysical properties and singlet-oxygen production. Helv. Chim. Acta, 74, 79–90.
- 34 Schmidt, R., C. Tanielian, R. Dunsbach, C. Wolff (1994) Phenalenone, a universal reference compound for the determination of quantum yields of singlet oxygen O2(1Δg) sensitization. J. Photochem. Photobiol. A:Chem, 79, 11–17.
- 35 Wilkinson, F., W.P. Helman, 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.