Comparative photophysical investigation of oxygen and sulfur as covalent linkers on octaalkylamino substituted zinc(II) phthalocyanines

This work describes a systematic comparison of oxygen and sulfur as covalent linkers on octasubstituted zinc(II) phthalocyaninates. Most photophysical parameters that make phthalocyanines technologically relevant, e.g. molar absorption coefficients, fluorescence, triplet and singlet oxygen quantum y...

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Autor principal: Strassert, C.A
Otros Autores: Bilmes, Gabriel Mario, Awruch, J., Dicelio, L.E
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 2008
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Acceso en línea:Registro en Scopus
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Sumario:This work describes a systematic comparison of oxygen and sulfur as covalent linkers on octasubstituted zinc(II) phthalocyaninates. Most photophysical parameters that make phthalocyanines technologically relevant, e.g. molar absorption coefficients, fluorescence, triplet and singlet oxygen quantum yields, are essentially unaffected by the substitution. The energy content of the first triplet state was observed to be close to the first singlet state of molecular oxygen for both spacers, as follows from photoacoustic determinations. Nonetheless, a bathochromic shift of 30 nm in the absorption and emission maxima, and of 60 nm in the triplet-triplet absorption spectra were observed when alkyloxyl and alkylsulfanyl moieties were alternatively present. Fluorescence quantum yields proved to be much more sensitive towards aggregation than the absorption spectra. Therefore, a novel fluorescence data analysis provided aggregation parameters and photophysical properties of the monomeric species. It was observed that the tendency towards dimerization is slightly higher with sulfur linkers. These results set a foundation for the rational design of conveniently substituted phthalocyaninates with different connectors between the macrocycle and the side chains. © The Royal Society of Chemistry and Owner Societies.
Bibliografía:(1989) Phthalocyanines, Properties and Applications, Ed., 1-4. , C. C. Leznoff and R. Lever, VCH, New York, 1993
Ali, H., Van Lier, J.E., Metal complexes as photo - And radiosensitizers (1999) Chem. Rev., 99, pp. 2379-2450
Gregory, P., Industrial applications of phthalocyanines (2000) J. Porphyrins Phthalocyanines, 4, pp. 432-437
Abdurrahmanoglu, S., Zkaya, A.R., Bulut, M., Bekaroglu, Synthesis, characterization, and electrochemical and electrochromic properties of sandwich dilutetium tetraphthalocyanine (2004) Dalton Trans., pp. 4022-4029
Fukuda, T., Ishiguro, T., Kobayashi, N., Non-planar phthalocyanines with Q-bands beyond 800 nm (2005) Tetrahedron Lett., 46, pp. 2907-2909
Pandey, R.K., Recent advances in photodynamic therapy (2000) J. Porphyrins Phthalocyanines, 4, pp. 368-373
Peng, Y., Lin, Z., Huang, J., Chen, N., Photophysics of lanthanide double-decker compounds with mixed octaethylporphyrinato and 2,3-naphthalocyaninato ligands (2005) Dyes Pigm., 67, pp. 145-150
Zhang, Q., Chen, H., Liu, Y., Huang, D., Study on the transformation of metal-free phthalocyanine polymorph crystals by organic solvent treatment (2004) Dyes Pigm., 63, pp. 11-16
Kato, K., Takahashi, K., Suzuki, K., Sato, T., Shinbo, K., Kaneko, F., Shimizu, H., Ohta, S., Organic light emitting diodes with nanostructured ultrathin layers at the interface between electron- and hole-transport layers (2005) Curr. Appl. Phys., 5, pp. 321-326
Liu, Y., Yu, G., Li, Q., Zhu, D., Synthesis and characterization of new poly(cyanoterephthalylidene)s for light-emitting diodes (2001) Synth. Met., 122, pp. 401-408
Hongbing, Z., Wenzhe, C., Minquan, W., Study on the optical limiting mechanism of metallo-phthalocyanine/silica gel glass composites (2005) Mater. Lett., 59, pp. 1395-1399
Qu, S., Chen, Y., Wang, Y., Song, Y., Liu, S., Zhao, X., Wang, D., Enhanced optical limiting properties in a novel metallophthalocyanine complex (C12H25O)8PcPb (2001) Mater. Lett., 51, pp. 534-538
Komolov, A., Moller, P.J., Unoccupied electronic band structure of conjugated molecular films interfacing polycrystalline gold surface (2005) Appl. Surf. Sci., 244, pp. 573-577
Zdravkovski, D., Milletti, M.C., A comparison of structural and electronic characteristics among subphthalocyanine and phthalocyanine complexes (2005) J. Mol. Struct. (THEOCHEM), 717, pp. 85-89
Huang, W., Xiang, H., Gong, Q., Huang, Y., Huang, C., Jiang, J., Large and ultrafast third-order optical nonlinearity of heteroleptic triple-decker (phthalocyaninato) (porphyrinato) Sm(III) complexes (2003) Chem. Phys. Lett., 374, pp. 639-644
Ma, G., Guo, L., Mi, J., Liu, Y., Qian, S., Pan, D., Huang, Y., Femtosecond nonlinear optical response of metallophthalocyanine films (2001) Solid State Commun., 118, pp. 633-638
Makhseed, S., Bumajad, A., Ghanem, B., Masayib, K., McKeown, N.B., Macrodiscotic liquid crystals derived from planar phthalocyanine oligomers (2004) Tetrahedron Lett., 45, pp. 4865-4868
Kim, J.Y., Bard, A.J., Organic donor/acceptor heterojunction photovoltaic devices based on zinc phthalocyanine and a liquid crystalline perylene diimide (2003) Chem. Phys. Lett., 383, pp. 11-15
Miyata, T., Minami, T., Chlorine gas sensors with high sensitivity using Mg-phthalocyanine thin films (2005) Appl. Surf. Sci., 244, pp. 563-567
Altindal, A., Öztürk, Z.Z., Dabak, S., Bekaroglu, Ö., Halogen sensing using thin films of crosswise-substituted phthalocyanines (2001) Sens. Actuators, B, 77, pp. 389-394
Ding, X., Xu, H., Gas-sensing properties of asymmetrically substituted amphiphilic phthalocyanines (2000) Sens. Actuators, B, 65, pp. 108-110
Abdurrahmanoglu, S., Altindal, A., Özkaya, A.R., Bulut, M., Bekaroglu, Ö., Synthesis, characterization, and electrical and electrochemical properties of sandwich dilutetium tetraphthalocyanine (2004) Chem. Commun., pp. 2096-2097
Pepe, E., Abbas, O., Rebufa, C., Simon, M., Lacombe, S., Julliard, M., Supported photosensitizers for the visible light activation of phenols towards oxygen (2005) J. Photochem. Photobiol., a, 170, pp. 143-149
Haber, J., Pamin, K., Poltowicz, J., Cationic metalloporphyrins and other macrocyclic compounds in zeolite matrix as catalysts for oxidation with dioxygen (2004) J. Mol. Catal. A: Chem., 224, pp. 153-159
Cao, Y.C., Jiang, X.Z., Supported palladium phthalocyanine catalysts in hydrodechlorination of CCl2F2 (2002) J. Mol. Catal. A: Chem., 184, pp. 183-189
Komolov, A., Moller, P.J., Interface formation between Cu-phthalocyanine films and CdS and GaAs semiconductor surfaces (2004) Colloids Surf. a, 239, pp. 49-54
Heutz, S., Sullivan, P., Sanderson, B.M., Sultes, S.M., Jones, T.S., Influence of molecular architecture and intermixing on the photovoltaic, morphological and spectroscopic properties of CuPc-C60 heterojunctions (2004) Sol. Energy Mater. Sol. Cells, 83, pp. 229-245
Armstrong, N.R., Carter, C., Donley, C., Simmonds, A., Lee, P., Brumbach, M., Kippelen, B., Yoo, S., Interface modification of ITO thin films: Organic photovoltaic cells (2003) Thin Solid Films, 445, pp. 342-352
Sakamoto, K., Kato, T., Ohno-Okumura, E., Watanabe, M., Cook, M.J., Synthesis of novel cationic amphiphilic phthalocyanine derivatives for next generation photosensitizer using photodynamic therapy of cancer (2005) Dyes Pigm., 64, pp. 63-71
Somani, P.R., Radhakrishnan, S., Electrochromic materials and devices: Present and future (2003) Mater. Chem. Phys., 77, pp. 117-133
Clarkson, G.J., McKeown, N.B., Treacher, K.E., Synthesis and characterization of some novel phthalocyanines containing both oligo(ethyleneoxy) and alkyl or alkoxy side-chains: Novel unsymmetrical discotic mesogens (1995) J. Chem. Soc., Perkin Trans 1, pp. 1817-1923
Kasuga, K., Mihara, T., Nakao, T., Takahashi, K., Electrical conductivity of octakis(decyloxy) phthalocyaninato-copper(II) (1991) Inorg. Chim. Acta, 189, pp. 11-12
Hauschel, B., Jung, R., Hanack, M., Synthesis and Diels-Alder reactions of some new nickel (phthalocyanine)nickel complexes (1999) Eur. J. Inorg. Chem., pp. 693-703
Kandaz, M., Yarasir, M.N.U., Koca, A., Bekaroglu, Ö., Synthesis, characterization and electrochemistry of novel differently octasubstituted phthalocyanines (2002) Polyhedron, 21, pp. 255-263
Kudrevich, S., Brasseur, N., La Madeleine, C., Gilbert, S., Van Lier, J.E., Syntheses and photodynamic activities of novel trisulfonated zinc phthalocyanine derivatives (1997) J. Med. Chem., 40, pp. 3897-3904
Oldham, T.C., Phillips, D., Triplet-state photophysics of aluminium phthalocyanine sensitizer in murine cancer cells (2000) J. Photochem. Photobiol., B, 55, pp. 16-19
Urizzi, P., Allen, C.M., Langlois, R., Ouellet, R., La Madeleine, C., Van Lier, J.E., Low-density lipoprotein-bound aluminum phthalocyanine: Targeting tumor cells for photodynamic therapy (2001) J. Porphyrins Phthalocyanines, 5, pp. 154-160
Boyle, R.W., Leznoff, C.C., Van Lier, J.E., Biological activities of phthalocyanines-XVI. tetrahydroxy and tetraalkylhydroxy zinc phthalocyanines. Effect of alkyl chain length on in vitro and in vivo photodynamic activities (1993) Br. J. Cancer, 62, pp. 1177-1181
Hu, M., Brasseur, N., Zeki Yildiz, S., Van Lier, J.E., Leznoff, C.C., Hydroxyphthalocyanines as potential photodynamic agents for cancer therapy (1998) J. Med. Chem., 41, pp. 1789-1802
Leznoff, C.C., Vigh, S., Svirskaya, P.I., Greenberg, S., Drew, D.M., Ben-Hur, E., Rosenthal, I., Synthesis and photocytotoxicity of some new substituted phthalocyanines (1989) Photochem. Photobiol., 49, pp. 279-284
Fernández, D.A., Dicelio, L.E., Awruch, J., Synthesis and properties of two novel N-alkyl substituted phthalocyanines (1995) J. Heterocyclic Chem., 32, pp. 519-522
Rodriguez, M.E., Strassert, C.A., Dicelio, L.E., Awruch, J., Synthesis of novel alkylamino zinc(II) phthalocyanines (2001) J. Heterocyclic Chem., 38, pp. 387-389
Fernández, D.A., Awruch, J., Dicelio, L.E., Synthesis and photophysical properties of a new cationic water-soluble Zn phthalocyanine (1997) J. Photochem. Photobiol., B, 41, pp. 227-232
De Filippis, M.P., Dei, D., Fantetti, L., Roncucci, G., Synthesis of a new water - Soluble octa-cationic phthalocyanine derivative for PDT (2000) Tetrahedron Lett., 41, pp. 9143-9147
Segalla, A., Borsarelli, C.D., Braslavsky, S.E., Spikes, J.D., Roncucci, G., Dei, D., Chiti, G., Reddi, E., Photophysical, photochemical and antibacterial photosensitizing properties of a novel octacationic Zn(II)-phthalocyanine (2002) Photochem. Photobiol. Sci., 1, pp. 641-648
Leznoff, B.C., Black, L.S., Hiebert, A., Causey, P.W., Christendat, D., Lever, A.B.P., Red manganese phthalocyanines from highly hindered hexadecaalcoxyphthalocyanines (2006) Inorg. Chim. Acta, 359, pp. 2690-2699
Cook, M.J., Chambrier, I., Cracknell, S.J., Mayes, D.A., Russell, D.A., Octa-alkyl zinc phthalocyanines: Potential photosensitizers for use in the photodynamic therapy of cancer (1995) Photochem. Photobiol., 62, pp. 542-545
Gürsoy, S., Cihan, A., Kocak, M.B., Bekaroglu, Ö., Synthesis of new metal-free and metal-containing phthalocyanines with tertiary or quaternary aminoethyl substituents (2001) Monatsh. Chem., 132, pp. 819-819
Ceyhan, T., Altindal, A., Erbil, M.K., Bekaroglu, -., Synthesis, characterization, conduction and gas sensing properties of novel multinuclear metallo phthalocyanines (Zn, Co) with alkylthio substituents (2006) Polyhedron, 25, pp. 737-746
Yazici, A., Ates, D., Bekaroglu, Ö., Kobayashi, N., Synthesis and characterization of novel azo-bridged Zn(II) and Co(II) bisphthalocyanines (2006) J. Porphyrins Phthalocyanines, 10, pp. 1140-1144
Kimura, T., Suzuki, T., Takaguchi, Y., Yomogita, A., Wakahara, T., Akasaka, T., Preparation and electrochemical properties of 1,4,8,11,15,18,22,25 octaalkylphthalocyanines containing four trithiole rings (2006) Eur. J. Org. Chem., pp. 1262-1270
Strassert, C.A., Rodriguez, M.E., Dicelio, L.E., Awruch, J., A synthetic approach towards novel octa-substituted zinc (II) phthalocyanines with different solubility and photophysical properties (2005) J. Porphyrins Phthalocyanines, 9, pp. 361-367
Strassert, C.A., Dicelio, L.E., Awruch, J., Reduction of an amido zinc(II) phthalocyanine by diborane (2006) Synthesis, pp. 799-802
Fernández, D.A., Awruch, J., Dicelio, L.E., Photophysical and aggregation studies of t-butyl-substituted Zn phthalocyanines (1996) Photochem. Photobiol., 63, pp. 784-792
Bensasson, R., Land, E.J., A general method for measuring triplet-triplet extinction coefficients, singlet-triplet intersystem crossing efficiencies, and related parameters (1978) Photochem. Photobiol. Rev., 3, pp. 163-191
Jacques, P., Braun, A.M., Laser flash photolysis of phthalocyanines in solution and microemulsion (1981) Helv. Chim. Acta, 64, pp. 1800-1805
Lagorio, M.G., Dicelio, L.E., San, E., Roman, Visible and near-IR spectroscopic and photochemical characterization of substituted metallophthalocyanines (1993) J. Photochem. Photobiol., a, 72, pp. 153-161
Brsalavsky, S.E., Heibel, G.E., Time-resolved photothermal and photoacoustic methods applied to photoinduced processes (1992) Chem. Rev., 92, pp. 1381-1410
Murov, S.L., (1973) Handbook of Photochemistry, , Marcel Dekker Inc., New York
Terazima, M., Azumi, T., A time resolved photoacoustic method with pulsed laser excitation in the condensed phase: The relation between signal intensity and decay-rate constant. (1990) Bull. Chem. Soc. Jpn., 63, pp. 741-745
Marti, C., Jurgens, O., Cuenca, O., Casals, M., Nonell, S., Aromatic ketones as standards for singlet molecular oxygen O 2(1Δg) photosensitation. Time resolved photoacoustic and near-IR emission studies (1996) J. Photochem. Photobiol., a, 97, pp. 11-18
ISSN:1474905X
DOI:10.1039/b802709a