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Volumn 73, Issue 5, 2001, Pages 473-481

Spectroscopic probing of the acid-base properties and photosensitization of a fluorinated phthalocyanine in organic solutions and liposomes

Author keywords

[No Author keywords available]

Indexed keywords

HEXADECA (2,2,2 TRIFLUOROETHOXY)PHTHALOCYANINE; HEXADECA-(2,2,2-TRIFLUOROETHOXY)PHTHALOCYANINE; INDOLE DERIVATIVE; LIPOSOME; PHOTOSENSITIZING AGENT;

EID: 0035347746     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1562/0031-8655(2001)0730473spotab2.0.co2     Document Type: Article
Times cited : (39)

References (57)
  • 1
    • 0027241935 scopus 로고
    • Titration in nonaqueous media: Potentiometric investigation of the basicity of meso-porphyrins in nitrobenzene solvent
    • Gündüz, T., N. Gündüz and M. Hayvaly (1993) Titration in nonaqueous media: potentiometric investigation of the basicity of meso-porphyrins in nitrobenzene solvent. Anal. Chim. Acta 278, 243-247.
    • (1993) Anal. Chim. Acta , vol.278 , pp. 243-247
    • Gündüz, T.1    Gündüz, N.2    Hayvaly, M.3
  • 2
    • 0342760028 scopus 로고    scopus 로고
    • Titrations in non-aqueous media: Potentiometric investigation of symmetrical and unsymmetrical tetra-aryl porphyrins with 4-nitrophenyl and 4-aminophenyl substituents in nitrobenzene solvent
    • Gündüz, N., T. Gündüz and M. Hayvali (1999) Titrations in non-aqueous media: potentiometric investigation of symmetrical and unsymmetrical tetra-aryl porphyrins with 4-nitrophenyl and 4-aminophenyl substituents in nitrobenzene solvent. Talanta 48, 71-79.
    • (1999) Talanta , vol.48 , pp. 71-79
    • Gündüz, N.1    Gündüz, T.2    Hayvali, M.3
  • 4
    • 0003019609 scopus 로고
    • Raman spectroscopy of inorganic species in solution
    • Edited by J. G. Grasselli and B. J. Bulkin, Wiley, New York
    • Irish, D. E. and T. Ozeki (1991) Raman spectroscopy of inorganic species in solution. In Analytical Raman Spectroscopy (Edited by J. G. Grasselli and B. J. Bulkin), pp. 59-106. Wiley, New York.
    • (1991) Analytical Raman Spectroscopy , pp. 59-106
    • Irish, D.E.1    Ozeki, T.2
  • 5
    • 0002312013 scopus 로고
    • Optical spectra and electronic structure of porphyrins and related rings
    • Edited by D. Dolphin, Academic Press, New York
    • Gouterman, M. (1978) Optical spectra and electronic structure of porphyrins and related rings. In The Porphyrins, Vol. III (Edited by D. Dolphin), pp. 1-165. Academic Press, New York.
    • (1978) The Porphyrins , vol.3 , pp. 1-165
    • Gouterman, M.1
  • 6
    • 0000129934 scopus 로고
    • Absorption and magnetic circular dichroism spectral properties of phthalocyanines. Part 1: Complexes of the dianion Pc(-2)
    • (Edited by C. C. Leznoff and A. B. P. Lever), VCH, Weinheim
    • Stillman, M. and T. Nyokong (1989) Absorption and magnetic circular dichroism spectral properties of phthalocyanines. Part 1: complexes of the dianion Pc(-2). In Phthalocyanines, Properties and Applications, Vol. 1 (Edited by C. C. Leznoff and A. B. P. Lever), pp. 133-289. VCH, Weinheim.
    • (1989) Phthalocyanines, Properties and Applications , vol.1 , pp. 133-289
    • Stillman, M.1    Nyokong, T.2
  • 7
    • 0042813364 scopus 로고
    • Spectra of porphyrins
    • Gouterman, M. (1961) Spectra of porphyrins. J. Mol. Spectrosc. 6, 138-163.
    • (1961) J. Mol. Spectrosc. , vol.6 , pp. 138-163
    • Gouterman, M.1
  • 9
    • 84887020267 scopus 로고
    • Über den einfluss von lösungsmitteln auf die absorptionsspektren gelöster absorbierender medien
    • Kundt, A. (1878) Über den einfluss von lösungsmitteln auf die absorptionsspektren gelöster absorbierender medien (On the influence of solvents on the absorption spectra of dissolved absorbing media). Poggendorfs Ann. Phys. Chem. 4, 34-54.
    • (1878) Poggendorfs Ann. Phys. Chem. , vol.4 , pp. 34-54
    • Kundt, A.1
  • 10
    • 17644402039 scopus 로고
    • Influence of the solvent on the absorption spectrum, reaction velocity and equilibrium
    • Scheibe, G., E. Felger and G. Rössler (1927) Influence of the solvent on the absorption spectrum, reaction velocity and equilibrium. Ber. Deutsch. Chem. Ges. 60, 1406-1419.
    • (1927) Ber. Deutsch. Chem. Ges. , vol.60 , pp. 1406-1419
    • Scheibe, G.1    Felger, E.2    Rössler, G.3
  • 11
    • 0001252287 scopus 로고
    • The effects of environment and aggregation on the absorption spectra of dyes
    • Sheppard, S. E. (1942) The effects of environment and aggregation on the absorption spectra of dyes. Rev. Mod. Phys. 14, 303-340.
    • (1942) Rev. Mod. Phys. , vol.14 , pp. 303-340
    • Sheppard, S.E.1
  • 12
    • 5844252510 scopus 로고
    • Solvatochromic dyes as solvent polarity indicators
    • Reichardt, C. (1994) Solvatochromic dyes as solvent polarity indicators. Chem. Rev. 94, 2319-2358.
    • (1994) Chem. Rev. , vol.94 , pp. 2319-2358
    • Reichardt, C.1
  • 14
    • 0039726458 scopus 로고
    • The solvatochromic comparison method. 6. The π* scale of solvent polarities
    • Kamlet, M. J., J. L. Abboud and R. W. Taft, (1977) The solvatochromic comparison method. 6. The π* scale of solvent polarities. J. Am. Chem. Soc. 99, 6027-6038.
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 6027-6038
    • Kamlet, M.J.1    Abboud, J.L.2    Taft, R.W.3
  • 17
    • 0000762919 scopus 로고
    • The basicities of the nitrogen atoms in the porphyrin nucleus; their dependence on some substituents of the tetrapyrrolic ring
    • Neuberger, A. and J. J. Scott (1952) The basicities of the nitrogen atoms in the porphyrin nucleus; their dependence on some substituents of the tetrapyrrolic ring. Proc. R. Soc. London, Ser. A 213, 307-326.
    • (1952) Proc. R. Soc. London, Ser. A , vol.213 , pp. 307-326
    • Neuberger, A.1    Scott, J.J.2
  • 19
    • 0000784626 scopus 로고
    • Dynamic coordination chemistry in metalloporphyrins
    • Chap. 6 (Edited by K. M. Smith), Elsevier, Amsterdam
    • Hambright, P. (1975) Dynamic coordination chemistry in metalloporphyrins. In Porphyrins and Metalloporphyrins, Chap. 6 (Edited by K. M. Smith), pp. 233-278. Elsevier, Amsterdam.
    • (1975) Porphyrins and Metalloporphyrins , pp. 233-278
    • Hambright, P.1
  • 20
    • 0022465198 scopus 로고
    • The photochemistry of haematoporphyrin and related systems
    • Pottier, R. and T. G Truscot (1986) The photochemistry of haematoporphyrin and related systems. Int. J. Radiat. Biol. 50, 421-452.
    • (1986) Int. J. Radiat. Biol. , vol.50 , pp. 421-452
    • Pottier, R.1    Truscot, T.G.2
  • 21
    • 0025441555 scopus 로고
    • Physical chemistry of porphyrins and their interactions with membranes: The importance of pH
    • Brault, D. (1990) Physical chemistry of porphyrins and their interactions with membranes: the importance of pH. J. Photochem. Photobiol. B: Biol. 6, 79-86.
    • (1990) J. Photochem. Photobiol. B: Biol. , vol.6 , pp. 79-86
    • Brault, D.1
  • 22
    • 0000967957 scopus 로고
    • Protonation equilibria of haematoporphyrin as studied by fluorescence lifetime analysis
    • Brault, D. and C. Vever-Bizet (1992) Protonation equilibria of haematoporphyrin as studied by fluorescence lifetime analysis. J. Chem. Soc. Faraday Trans. I 88, 1519-1524.
    • (1992) J. Chem. Soc. Faraday Trans. I , vol.88 , pp. 1519-1524
    • Brault, D.1    Vever-Bizet, C.2
  • 23
    • 0026545211 scopus 로고
    • Effects of pH on the binding of hematoporphyrin derivative to monolayer and bilayer membranes
    • Rich, M. R., G. Ferraro and S. S. Brody (1992) Effects of pH on the binding of hematoporphyrin derivative to monolayer and bilayer membranes. Biochim. Biophys. Acta 1104, 269-272.
    • (1992) Biochim. Biophys. Acta , vol.1104 , pp. 269-272
    • Rich, M.R.1    Ferraro, G.2    Brody, S.S.3
  • 24
    • 0027524765 scopus 로고
    • Interactions of dicarboxylic porphyrins with membranes in relation to their ionization state
    • Brault, D., C. Vever-Bizet and K. Kuzelova (1993) Interactions of dicarboxylic porphyrins with membranes in relation to their ionization state. J. Photochem. Photobiol. B: Biol. 20, 191-195.
    • (1993) J. Photochem. Photobiol. B: Biol. , vol.20 , pp. 191-195
    • Brault, D.1    Vever-Bizet, C.2    Kuzelova, K.3
  • 25
    • 0028872048 scopus 로고
    • Photophysical properties of porphyrins in biological membranes
    • Ricchelli, F. (1995) Photophysical properties of porphyrins in biological membranes. J. Photochem. Photobiol. B: Biol. 29, 109-118.
    • (1995) J. Photochem. Photobiol. B: Biol. , vol.29 , pp. 109-118
    • Ricchelli, F.1
  • 27
    • 0025618463 scopus 로고
    • The possible role of ionic species in selective biodistribution of photochemotherapeutic agents toward neoplastic tissue
    • Pottier, R. and J. C. Kennedy (1990) The possible role of ionic species in selective biodistribution of photochemotherapeutic agents toward neoplastic tissue. J. Photochem. Photobiol. B: Biol. 8, 1-16.
    • (1990) J. Photochem. Photobiol. B: Biol. , vol.8 , pp. 1-16
    • Pottier, R.1    Kennedy, J.C.2
  • 28
    • 0022255054 scopus 로고
    • Factors affecting the photokilling of Chinese hamster cells by phthalocyanines
    • Ben-Hur, E. and I. Rosenthal (1985) Factors affecting the photokilling of Chinese hamster cells by phthalocyanines. Radiat. Res. 103, 403-409.
    • (1985) Radiat. Res. , vol.103 , pp. 403-409
    • Ben-Hur, E.1    Rosenthal, I.2
  • 29
    • 0001046258 scopus 로고
    • The acid-base equilibria kinetics of copper ion incorporation and acid-catalyzed zinc ion displacement from the water-soluble porphyrin α,β,γ,δ-tetra(4-N-methylpyridyl)porphine
    • Hambright, P. and E. B. Fleischer (1970) The acid-base equilibria kinetics of copper ion incorporation and acid-catalyzed zinc ion displacement from the water-soluble porphyrin α,β,γ,δ-tetra(4-N-methylpyridyl)porphine. Inorg. Chem. 9, 1757-1761.
    • (1970) Inorg. Chem. , vol.9 , pp. 1757-1761
    • Hambright, P.1    Fleischer, E.B.2
  • 30
    • 0041803294 scopus 로고
    • Pulse radiolysis of porphyrin and ferriporphyrin solutions in 2-propanol-carbon tetrachloride systems. Protonation and ligand exchange kinetics
    • Brault, D. and P. Neta (1983) Pulse radiolysis of porphyrin and ferriporphyrin solutions in 2-propanol-carbon tetrachloride systems. Protonation and ligand exchange kinetics. J. Phys. Chem. 87, 3320-3327.
    • (1983) J. Phys. Chem. , vol.87 , pp. 3320-3327
    • Brault, D.1    Neta, P.2
  • 31
    • 0000437578 scopus 로고
    • Sequential protonation of meso-(p-(dimethylamino)phenyl) porphyrins: Charge transfer excited states producing hyperporphyrins
    • Ojadi, E. C. A., H. Linschitz, M. Gouterman, R. I. Walter, J. S. Lindsey, R. W. Wagner, P. R. Droupadi and W. Wang (1993) Sequential protonation of meso-(p-(dimethylamino)phenyl) porphyrins: charge transfer excited states producing hyperporphyrins. J. Phys. Chem. 97, 13 192-13 197.
    • (1993) J. Phys. Chem. , vol.97 , pp. 13192-13197
    • Ojadi, E.C.A.1    Linschitz, H.2    Gouterman, M.3    Walter, R.I.4    Lindsey, J.S.5    Wagner, R.W.6    Droupadi, P.R.7    Wang, W.8
  • 32
    • 0003898138 scopus 로고
    • Solvent effects on electronic states of phthalocyanines
    • Harazono, T. and I. Takagishi (1993) Solvent effects on electronic states of phthalocyanines. Bull. Chem. Soc. Jpn 66, 1016-1023.
    • (1993) Bull. Chem. Soc. Jpn , vol.66 , pp. 1016-1023
    • Harazono, T.1    Takagishi, I.2
  • 33
    • 0004122171 scopus 로고
    • Acid-base behaviour of phthalocyanine
    • Ledson, D. L. and M. V. Twingg (1975) Acid-base behaviour of phthalocyanine. Inorg. Chim. Acta 13, 43-46.
    • (1975) Inorg. Chim. Acta , vol.13 , pp. 43-46
    • Ledson, D.L.1    Twingg, M.V.2
  • 34
    • 0345697648 scopus 로고
    • Spectra of porphyrins and their acid salts
    • Aronof, S. and C. A. Weast (1941) Spectra of porphyrins and their acid salts. J. Org. Chem. 6, 550-557.
    • (1941) J. Org. Chem. , vol.6 , pp. 550-557
    • Aronof, S.1    Weast, C.A.2
  • 35
    • 17644381554 scopus 로고
    • Simultaneous dissociation of two protons. Acid-base equilibria of porphyrins
    • Walter, R. I. (1953) Simultaneous dissociation of two protons. Acid-base equilibria of porphyrins. J. Am. Chem. Soc. 75, 3860-3862.
    • (1953) J. Am. Chem. Soc. , vol.75 , pp. 3860-3862
    • Walter, R.I.1
  • 36
    • 17644421356 scopus 로고
    • The acid-base equilibria of porphyrins. Nonsimultaneous dissociation of two protons upheld
    • Scott, J. J. (1955) The acid-base equilibria of porphyrins. Nonsimultaneous dissociation of two protons upheld. J. Am. Chem. Soc. 77, 325-326.
    • (1955) J. Am. Chem. Soc. , vol.77 , pp. 325-326
    • Scott, J.J.1
  • 38
    • 0027604077 scopus 로고
    • Singlet oxygen generation by porphyrins and the kinetis of 9,10-dimethylanthracene photosensitization in liposomes
    • Gross, E., B. Ehrenberg and F. M. Johnson (1993) Singlet oxygen generation by porphyrins and the kinetis of 9,10-dimethylanthracene photosensitization in liposomes. Photochem. Photobiol. 57, 808-813.
    • (1993) Photochem. Photobiol. , vol.57 , pp. 808-813
    • Gross, E.1    Ehrenberg, B.2    Johnson, F.M.3
  • 40
    • 0000895490 scopus 로고
    • On the diffusion length of singlet oxygen in cells and tissue
    • Moan, J. (1990) On the diffusion length of singlet oxygen in cells and tissue. J. Photochem. Photobiol. B: Biol. 6, 343-344.
    • (1990) J. Photochem. Photobiol. B: Biol. , vol.6 , pp. 343-344
    • Moan, J.1
  • 41
    • 0025928204 scopus 로고
    • Quenching of singlet oxygen by human red cell ghosts
    • Kanofsky, J. R. (1991) Quenching of singlet oxygen by human red cell ghosts. Photochem. Photobiol. 53, 93-99.
    • (1991) Photochem. Photobiol. , vol.53 , pp. 93-99
    • Kanofsky, J.R.1
  • 42
    • 0027585670 scopus 로고
    • Time-resolved studies of singlet-oxygen emission from 11210 leukemia cells labeled with 5-(N-hexadecanoyl)amino eosin - A comparison with a one-dimensional model of singlet-oxygen diffusion and quenching
    • Baker, A. and J. R. Kanofsky (1993) Time-resolved studies of singlet-oxygen emission from 11210 leukemia cells labeled with 5-(N-hexadecanoyl)amino eosin - a comparison with a one-dimensional model of singlet-oxygen diffusion and quenching. Photochem. Photobiol. 57, 720-727.
    • (1993) Photochem. Photobiol. , vol.57 , pp. 720-727
    • Baker, A.1    Kanofsky, J.R.2
  • 43
    • 84989757489 scopus 로고
    • Singlet oxygen generation from liposomes: A comparison of time-resolved 1270 nm emission with singlet oxygen kinetics calculated from a one dimensional model of singlet-oxygen diffusion and quenching
    • Fu, Y. and J. R. Kanofsky (1995) Singlet oxygen generation from liposomes: a comparison of time-resolved 1270 nm emission with singlet oxygen kinetics calculated from a one dimensional model of singlet-oxygen diffusion and quenching. Photochem. Photobiol. 62, 692-702.
    • (1995) Photochem. Photobiol. , vol.62 , pp. 692-702
    • Fu, Y.1    Kanofsky, J.R.2
  • 44
    • 0000583506 scopus 로고    scopus 로고
    • Singlet-oxygen generation from liposomes: A comparison of 6 beta-cholesterol hydroperoxidc formation with predictions from a one-dimensional model of singlet-oxygen diffusion and quenching
    • Fu, Y., P. D. Sima and J. R. Kanofsky (1996) Singlet-oxygen generation from liposomes: a comparison of 6 beta-cholesterol hydroperoxidc formation with predictions from a one-dimensional model of singlet-oxygen diffusion and quenching. Photochem. Photobiol. 63, 468-476.
    • (1996) Photochem. Photobiol. , vol.63 , pp. 468-476
    • Fu, Y.1    Sima, P.D.2    Kanofsky, J.R.3
  • 45
    • 0001364502 scopus 로고
    • Chemistry of superoxide ion. Quenching of singlet oxygen
    • Guiraud, H. J. and C. S. Foote (1976) Chemistry of superoxide ion. Quenching of singlet oxygen. J. Am. Chem. Soc. 98, 1984-1986.
    • (1976) J. Am. Chem. Soc. , vol.98 , pp. 1984-1986
    • Guiraud, H.J.1    Foote, C.S.2
  • 46
    • 0017293852 scopus 로고
    • The quenching of iodide ion on singlet oxygen
    • Rosenthal, I. and A. Frimer (1976) The quenching of iodide ion on singlet oxygen. Photochem. Photobiol. 23, 209-211.
    • (1976) Photochem. Photobiol. , vol.23 , pp. 209-211
    • Rosenthal, I.1    Frimer, A.2
  • 47
    • 0015497808 scopus 로고
    • Nitrogen-hydrogen tautomerism in porphyrins and chlorins
    • Storm, C. B. and Y. Teklu (1972) Nitrogen-hydrogen tautomerism in porphyrins and chlorins. J. Am. Chem. Soc. 94, 1745-1747.
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 1745-1747
    • Storm, C.B.1    Teklu, Y.2
  • 49
    • 37049113275 scopus 로고
    • Dynamic proton and nitrogen-15 nuclear magnetic resonance of free-base 15N-porphyrins
    • Irving, C. S. and A. Lapidot (1977) Dynamic proton and nitrogen-15 nuclear magnetic resonance of free-base 15N-porphyrins. J. Chem. Soc. Chem. Commun. 184-186.
    • (1977) J. Chem. Soc. Chem. Commun. , pp. 184-186
    • Irving, C.S.1    Lapidot, A.2
  • 50
    • 33845281388 scopus 로고
    • Kinetic of tautomerism in 2-substituted 5,10,15,20-tetraphenylpophyrins: Directionality of proton transfer between the inner nitrogens
    • Crossley, M. J., L. D. Field, M. M. Harding and S. Sternhell (1987) Kinetic of tautomerism in 2-substituted 5,10,15,20-tetraphenylpophyrins: directionality of proton transfer between the inner nitrogens. J. Am. Chem. Soc. 109, 2335-2341.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 2335-2341
    • Crossley, M.J.1    Field, L.D.2    Harding, M.M.3    Sternhell, S.4
  • 52
    • 0026598535 scopus 로고
    • 1H NMR spectroscopy: Substituent effects and structure implications
    • 1H NMR spectroscopy: substituent effects and structure implications. J. Org. Chem. 57, 1833-1837.
    • (1992) J. Org. Chem. , vol.57 , pp. 1833-1837
    • Harding, M.M.1    Sternhell, S.2
  • 53
    • 0000198734 scopus 로고
    • 1H NMR N-H line shape analysis for meso-monosubstituted octaethylporphyrines: An indication of remarkably slow N-H tautomerism
    • 1H NMR N-H line shape analysis for meso-monosubstituted octaethylporphyrines: an indication of remarkably slow N-H tautomerism. J. Org. Chem. 57, 5796-5798.
    • (1992) J. Org. Chem. , vol.57 , pp. 5796-5798
    • Asakawa, M.1    Toi, H.2    Aoyama, Y.3    Ogoshi, H.4
  • 54
    • 9344252788 scopus 로고    scopus 로고
    • Observation of kinetic tritium isotope effects by dynamic NMR. The tautomerism of porphyrin
    • Braun, J., H. H. Limbach, P. G. Williams, H. Morimoto and D. E. Wemmer (1996) Observation of kinetic tritium isotope effects by dynamic NMR. The tautomerism of porphyrin. J. Am. Chem. Soc. 118, 7231-7232.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 7231-7232
    • Braun, J.1    Limbach, H.H.2    Williams, P.G.3    Morimoto, H.4    Wemmer, D.E.5
  • 55
    • 84989040092 scopus 로고
    • Solution phase proton and carbon-13-NMR studies of some 1,4,8,11,18,22,25-octaalkylphthalocyanines
    • Cook, M. J., S. J. Cracknell, G. R. Moore, M. J. Osborne and D. J. Williamson (1991) Solution phase proton and carbon-13-NMR studies of some 1,4,8,11,18,22,25-octaalkylphthalocyanines. Magn. Reson. Chem. 29, 1053-1060.
    • (1991) Magn. Reson. Chem. , vol.29 , pp. 1053-1060
    • Cook, M.J.1    Cracknell, S.J.2    Moore, G.R.3    Osborne, M.J.4    Williamson, D.J.5
  • 56
    • 0002225997 scopus 로고
    • Edited by E. F. Mooney, Academic Press, London
    • Sutherland, I. O. (1971) In Annual Reports in NMR Spectroscopy, Vol. 4 (Edited by E. F. Mooney), pp. 71-235. Academic Press, London. (See specifically p. 80)
    • (1971) Annual Reports in NMR Spectroscopy , vol.4 , pp. 71-235
    • Sutherland, I.O.1
  • 57
    • 0000086443 scopus 로고
    • NMR study of environment modulated proton tautomerism in crystalline and amorphous phthalocyanine
    • Wehrle, B. and H. H. Limbach (1989) NMR study of environment modulated proton tautomerism in crystalline and amorphous phthalocyanine. Chem. Phys. 136, 223-247.
    • (1989) Chem. Phys. , vol.136 , pp. 223-247
    • Wehrle, B.1    Limbach, H.H.2


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