Highly soluble 7-oxy-3-(4-methoxyphenyl)coumarin bearing zinc phthalocyanines: Synthesis and investigation of photophysical and photochemical properties

Jones, 1985, Solvent effects on emission yield and lifetime for coumarin laser dyes. Requirements for a rotatory decay mechanism, J. Phys. Chem., 89, 294, 10.1021/j100248a024 Murray, 1982 Marshall, 1994, An updated review of the clinical development of coumarin (1,2-benzopyrone) and 7-hydroxycoumarin, J. Cancer Res. Clin. Oncol., 120, 39, 10.1007/BF01377124 Moran, 1993, The effect of coumarin and 7-hydroxycoumarin on the growth of human tumor cell lines, J. Irish Coll. Phys. Surg., 22, 41 Thornes, 1989, Prevention of early recurrence of high risk malignant melanoma by coumarin, Eur. J. Surg. Oncol., 15, 431 Raev, 1990, Antitumor activity of some coumarin derivatives, Die Pharmazie, 45, 696 Maucher, 1994, Antitumor activity of coumarin and 7-hydroxycoumarin against 7,12-dimethylbenz[α]anthracene-induced rat mammary carcinomas, J. Cancer Res. Clin. Oncol., 120, 502, 10.1007/BF01191806 Thornes, 1994, Treatment with coumarin to prevent or delay recurrence of malignant melanoma, J. Cancer Res. Clin. Oncol., 120, 32, 10.1007/BF01377122 Mohler, 1992, Phase II evaluation of coumarin (1,2-benzopyrone) in metastatic prostatic carcinoma, Prostate, 20, 123, 10.1002/pros.2990200208 Kolodziej, 1997, Structure–cytotoxicity relationships of a series of natural and semisynthetic simple coumarins as assessed in two human tumour cell lines, Z. Naturforsch., 52, 240, 10.1515/znc-1997-3-416 Walter, 2010, Porphyrins and phthalocyanines in solar photovoltaic cells, J. Porphyrins Phthalocyanines, 14, 759, 10.1142/S1088424610002689 Loi, 2003, Long-lived photoinduced charge separation for solar cell applications in phthalocyanine–fulleropyrrolidine dyad thin films, J. Mater. Chem., 13, 700 2003, vols. 15–20 Beck, 1991, Lösliche (tetraethylphthalocyaninato)eisen(II)- und-cobalt(II)-Verbindungen, Chem. Ber., 124, 2315, 10.1002/cber.19911241026 Dumoulin, 2010, Synthetic pathways to water-soluble phthalocyanines, Coord. Chem. Rev., 254, 2792, 10.1016/j.ccr.2010.05.002 Dudkowiak, 2006, Photophysical studies of tetratolylporphyrin photosensitizers for potential medical applications, J. Mol. Struct., 792–793, 93, 10.1016/j.molstruc.2005.12.052 Staskowiak, 2004, Spectral properties of stilbazolium merocyanines – potential sensitizers in photodynamic therapy and diagnosis. Part I. Merocyanines in model systems, J. Photochem. Photobiol. A: Chem., 163, 127, 10.1016/S1010-6030(03)00439-8 Wröbel, 2006, Porphyrins and phthalocyanines – functional molecular materials for optoelectronics and medicine, Mol. Cryst. Liq. Cryst., 448, 15, 10.1080/15421400500377354 Frackowiak, 2003, Applications of photothermic methods in photodynamic therapy, J. Phys. IV, 109, 33, 10.1051/jp4:20030649 Staskowiak, 2005, Photostability and the yield of triplet state generation of bacteriochlorophyll c and bacteriopheophytin c in solution, Spectrochim. Acta A, 61, 2033, 10.1016/j.saa.2004.08.004 Rosenthal, 1991, Phthalocyanines as photodynamic sensitizers, Photochem. Photobiol., 53, 859, 10.1111/j.1751-1097.1991.tb09900.x Rosenthal, 1996, 4, 481 Ben-Hur, 1985, The phthalocyanines: a new class of mammalian cells photosensitizers with a potential for cancer phototherapy, Int. J. Radiat. Biol., 47, 145, 10.1080/09553008514550211 Bishop, 1995, The preparation and photophysical measurements of perdeutero zinc phthalocyanine, J. Photochem. Photobiol. A: Chem., 90, 39, 10.1016/1010-6030(95)04095-W Esenpınar, 2010, Tetra-3-[(2-diethylamino)ethyl]-7-oxo-4-methyl coumarin-substituted zinc phthalocyanines: synthesis, characterization and aggregation effects on photophysical/photochemical properties, J. Photochem. Photobiol. A: Chem., 213, 171, 10.1016/j.jphotochem.2010.05.021 Louati, 1985, Electrochemical reduction of new, good electron acceptors: the metallooctacyanophthalocyanines, Inorg. Chem., 24, 1175, 10.1021/ic00202a012 Wöhrle, 1988, Octabutoxyphthalocyanine, a new electron donor, J. Chem. Soc. Dalton Trans., 549, 10.1039/DT9880000549 Hale, 1987, The electronic structure of substituted phthalocyanines: a Hartree-Fock-Slater study of octacyano- and octafluoro-substituted (phthalocyaninato)silicon dihydroxide, J. Am. Chem. Soc., 109, 5943, 10.1021/ja00254a007 Schlettwein, 1994, Correlation of frontier orbital positions and conduction type of molecular semiconductors as derived from ups in combination with electrical and photoelectrochemical experiments, J. Phys. Chem., 98, 11771, 10.1021/j100096a023 Meier, 1986, Correlation of chemical structure to photoconductivity: octacyano- and octamethoxy-substituted zinc phthalocyanine, J. Phys. Chem., 90, 6349, 10.1021/j100281a057 Maree, 2001, Syntheses and photochemical properties of octasubstituted phthalocyaninato zinc complexes, J. Porphyrins Phthalocyanines, 5, 782, 10.1002/jpp.388 Law, 1997, Synthesis and spectroscopic properties of octasubstituted (phthalocyaninato)titanium(IV) complexes, Inorg. Chim. Acta, 256, 147, 10.1016/S0020-1693(96)05420-5 Kobayashi, 2003, Substituent effect on the electronic and fluorescence spectra of metal-free and zinc phthalocyanines, Chem. Eur. J., 9, 5123, 10.1002/chem.200304834 Ferencz, 1995, Synthesis and spectroscopic properties of phthalocyanine dimers in solution, Chem. Phys. Lett., 245, 23, 10.1016/0009-2614(95)00978-D Michelsen, 1996, Unsymmetrically substituted benzonaphthoporphyrazines: a new class of cationic photosensitizers for the photodynamic therapy of cancer, Photochem. Photobiol., 64, 694, 10.1111/j.1751-1097.1996.tb03126.x Perrin, 1989 Bhandari, 1949, Studies in the 3-phenyl coumarin series. Part 1. Synthesis of some new members of the series, J. Sci. Ind. Res., 8B, 189 Young, 1990, Synthesis and characterization of di-disubstituted phthalocyanines, J. Org. Chem., 55, 2155, 10.1021/jo00294a032 George, 1995, Synthesis of 3-nitrophthalonitrile and tetra-alpha-substituted phthalocyanines, J. Heterocyclic Chem., 32, 495, 10.1002/jhet.5570320219 Wöhrle, 1993, A simple synthesis of 4,5-disubstituted 1,2-dicyanobenzenes and 2,3,9,10,16,17,23,24-octasubstituted phthalocyanines, Synthesis, 2, 194, 10.1055/s-1993-25825 Maree, 2002, Effects of axial ligands on the photophysical properties of silicon octaphenoxyphthalocyanine, J. Porphyrins Phthalocyanines, 6, 373, 10.1142/S1088424602000452 Ogunsipe, 2004, Photophysical and photochemical studies of zinc(II) phthalocyanine derivatives – effects of substituents and solvents, New J. Chem., 28, 822, 10.1039/B315319C Strickler, 1962, Relationship between absorption intensity and fluorescence lifetime of molecules, J. Chem. Phys., 37, 814, 10.1063/1.1733166 Du, 1998, PhotochemCAD: a computer-aided design and research tool in photochemistry, Photochem. Photobiol., 68, 141 Seotsanyana-Mokhosi, 2001, Photochemical studies of tetra-2,3-pyridinoporphyrazines, J. Photochem. Photobiol. A: Chem., 140, 215, 10.1016/S1010-6030(01)00427-0 Spliller, 1998, Singlet oxygen quantum yields of different photosensitizers in polar solvents and micellar solutions, J. Porphyrins Phthalocyanines, 2, 145, 10.1002/(SICI)1099-1409(199803/04)2:2<145::AID-JPP60>3.0.CO;2-2 Rose, 1964 Atilla, 2007, Synthesis, photophysical and photochemical properties of poly(oxyethylene)-substituted zinc phthalocyanines, Dalton Trans., 12, 1235, 10.1039/B617773E Gürol, 2010, Photophysical and photochemical properties of fluorinated and nonfluorinated n-propanol-substituted zinc phthalocyanines, Eur. J. Inorg. Chem., 8, 1220, 10.1002/ejic.200901096 Stillman, 1989, vol. 1 Nyokong, 2010, vol. 7, 247 Nyokong, 2007, Effects of substituents on the photochemical and photophysical properties of main group metal phthalocyanines, Coord. Chem. Rev., 251, 1707, 10.1016/j.ccr.2006.11.011 Anderson, 1985, Electronic and redox properties of stacked-ring silicon pthalocyanines from molecular orbital theory, J. Am. Chem. Soc., 107, 192, 10.1021/ja00287a034 Engelkamp, 2000, Molecular materials based on crown ether functionalized phthalocyanines, J. Porphyrins Phthalocyanines, 4, 454, 10.1002/1099-1409(200008)4:5<454::AID-JPP261>3.0.CO;2-D Yang, 1985, Dimerization of cobalt(II) tetrasulfonated phthalocyanine in water and aqueous alcoholic solutions, Inorg. Chem., 24, 1765, 10.1021/ic00206a011 Schutte, 1993, Aggregation of an octasubstituted phthalocyanine in dodecane solution, J. Phys. Chem., 97, 6069, 10.1021/j100124a047 Osburn, 1996, Novel amphiphilic phthalocyanines: formation of Langmuir–Blodgett and cast thin films, Langmuir, 12, 4784, 10.1021/la960032t Dominquez, 2001, Polyethyleneoxide-capped phthalocyanines: limiting phthalocyanine aggregation to dimer formation, J. Porphyrins Phthalocyanines, 5, 582, 10.1002/jpp.365 Martin, 1991, Effects of ligands, solvent, and variable sulfonation on dimer formation of aluminum and zinc phthalocyaninesulfonates, Inorg. Chem., 30, 3305, 10.1021/ic00017a016 Li, 1999, Efficient synthesis of light-harvesting arrays composed of eight porphyrins and one phthalocyanine, J. Org. Chem., 64, 9101, 10.1021/jo991102e Zorlu, 2010, Comparative studies of photophysical and photochemical properties of solketal substituted platinum(II) and zinc(II) phthalocyanine sets, Tetrahedron, 66, 3248, 10.1016/j.tet.2010.02.079 Saka, 2011, Solvent and central metal effects on the photophysical and photochemical properties of 4-benzyloxybenzoxy substituted phthalocyanines, J. Organomet. Chem., 696, 913, 10.1016/j.jorganchem.2010.10.024 Durmuş, 2007, Photophysical and photochemical studies of long chain-substituted zinc phthalocyanines, J. Photochem. Photobiol. A: Chem., 186, 323, 10.1016/j.jphotochem.2006.08.025 Atilla, 2007, Synthesis, photophysical and photochemical properties of poly(oxyethylene)-substituted phthalocyaninato oxotitanium(IV) complexes, Eur. J. Inorg. Chem., 3573, 10.1002/ejic.200700057 Murov, 1993