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Published in:
Design and Conception of Photosensitisers Read chapter Read first chapter

2012 | OriginalPaper | Chapter

4. Photochemical and Photophysical Characterization

Author : Mahmut Durmuş

Published in: Photosensitizers in Medicine, Environment, and Security

Publisher: Springer Netherlands

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Abstract

This chapter highlights the photophysical and photochemical parameters of photosensitizers, with a focus on the different measuring and calculation methods. Singlet oxygen generation, photodegradation quantum yield, fluorescence quantum yield and lifetime and triple state quantum yield and lifetime of the photosensitizers are detailed and data regarding these parameters for photosensitizing phthalocyanines are summarized. The effects of number and position of substituents, nature of central metal and solvents on these parameters of phthalocyanine photosensitizers are also given in Table 4.1.

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previous chapter The Contribution of Theoretical Chemistry to the Drug Design in Photodynamic Therapy
next chapter Sensitization of Singlet Oxygen Formation in Aqueous Media
Literature
1.
Tedesco AC, Rotta JCG, Lunardi CN (2003) Synthesis, photophysical and photochemical aspects of phthalocyanines for photodynamic therapy. Curr Org Chem 7:187–196
2.
Ali H, van Lier JE (1999) Metal complexes as photo- and radiosensitizers. Chem Rev 99:2379–2450
3.
Moan J, Peng Q (2003) An outline of the history of PDT. In: Patrice T (ed) Photodynamic therapy. The Royal Society of Chemistry, Cambridge, pp 1–18
4.
Dougherty TJ (1984) Photodynamic therapy (PDT) of malignant tumors. Crit Rev Oncol Hematol 2:83–116
5.
Rousset N, Bourr L, Thibaud S (2003) Sensitizers in photodynamic therapy. In: Patrice T (ed) Photodynamic therapy. The Royal Society of Chemistry, Cambridge, pp 59–80
6.
Okura I (2000) Photosensitization of porphyrins and phthalocyanines. Gordon and Breach Science Publishers, Amsterdam
7.
Phillips D (1995) The photochemistry of sensitisers for photodynamic therapy. Pure Appl Chem 67:117–126
8.
Bonnett R (1995) Photosensitizers of the porphyrin and phthalocyanine series for photodynamic therapy. Chem Soc Rev 24:19–33
9.
Redmond RW (2008) Photophysics and photochemistry in photodynamic therapy. In: Hamblin MR, Mroz P (eds) Advances in photodynamic therapy: basic, translational, and clinical. Artech House, Boston and London, pp 41–58
10.
Zorlu Y, Dumoulin F, Durmuş M, Ahsen V (2010) Comparative studies of photophysical and photochemical properties of solketal substituted platinum(II) and zinc(II) phthalocyanine sets. Tetrahedron 66:3248–3258
11.
Grossweiner LI, Jones LR, Grossweiner JB, Rogers BHG (2005) The science of phototherapy: an introduction. Springer, Dordrecht
12.
Bonnett R (2000) Chemical aspects of photodynamic therapy. Gordon and Breach Science, Amsteldijk, pp 199–222
13.
Patterson MS, Madsen SJ, Wilson R (1990) Experimental tests of the feasibility of singlet oxygen luminescence monitoring in vivo during photodynamic therapy. J Photochem Photobiol B Biol 5:69–84
14.
Foley S, Jones G, Liuzzi R, McGarvey DJ, Perry HM, Truscott TG (1997) The synthesis and photophysical properties of polyether substituted phthalocyanines of potential use in photo­dynamic therapy. J Chem Soc Perkin Trans 29:1725–1730
15.
Rosenthal I, Ben-Hur E (1995) Role of oxygen in the phototoxicity of phthalocyanines. Int J Radiat Biol 67:85–91
16.
Ogunsipe A, Chen JY, Nyokong T (2004) Photophysical and photochemical studies of zinc(II) phthalocyanine derivatives—effects of substituents and solvents. New J Chem 28:822–827
17.
Kuznetsova NA, Gretsova NS, Derkacheva VM, Mikhalenko SA, Solov’eva LI, Yuzhakova OA, Kaliya OL, Luk’yanets EA (2002) Generation of singlet oxygen with anionic aluminum phthalocyanines in water. Russ J Gen Chem 72:300–306
18.
Shen T, Yuan ZL, Xu HY (1989) Fluorescent properties of phthalocyanines. Dyes Pigm 11:77–80
19.
Maree D, Nyokong T, Suhling K, Phillips D (2002) Effects of axial ligands on the photophysical properties of silicon octaphenoxyphthalocyanine. J Porphyrins Phthalocyanines 6:373–376
20.
Maree S, Phillips D, Nyokong T (2002) Synthesis, photophysical and photochemical studies of germanium and tin phthalocyanine complexes. J Porphyrins Phthalocyanines 6:17–25
21.
Atilla D, Durmuş M, Gürek AG, Ahsen V, Nyokong T (2007) Synthesis, photophysical and photochemical properties of poly(oxyethylene)-substituted zinc phthalocyanines. Dalton Trans 2007:1235–1243
22.
Seotsanyana-Mokhosi I, Kuznetsova N, Nyokong T (2001) Photochemical studies of tetra-2,3-pyridinoporphyrazines. J Photochem Photobiol A Chem 140:215–222
23.
Ogunsipe A, Maree D, Nyokong T (2003) Solvent effects on the photochemical and fluorescence properties of zinc phthalocyanine derivatives. J Mol Struct 650:131–140
24.
Fernandez JM, Bilgin MD, Grossweiner LI (1997) Singlet oxygen generation by photo­dynamic agents. J Photochem Photobiol B Biol 37:131–140
25.
Grossweiner LI (1995) Photodynamic therapy. J Laser Appl 7:51–57
26.
Moan J, Wold E (1979) Detection of singlet oxygen production by ESR. Nature 279:450–451
27.
Lavi R, Sinyakov M, Samuni A, Shatz S, Friedmann H, Shainberg A, Breitbart H, Lubart R (2004) ESR detection of 1O2 reveals enhanced redox activity in illuminated cell cultures. Free Radic Res 38:893–902
28.
Schnurpfeil G, Sobbi AK, Spiller W, Kliesch H, Wöhrle D (1997) Photo-oxidative stability and its correlation with semi-empirical MO calculations of various tetraazaporphyrin derivatives in solution. J Porphyrins Phthalocyanines 1:159–167
29.
Ozoemena K, Kutznetsova N, Nyokong T (2001) Comparative photosensitised transformation of polychlorophenols with different sulphonated metallophthalocyanine complexes in aqueous medium. J Mol Catal A Chem 176:29–40
30.
Spiller W, Kliesch H, Wöhrle D, Hackbarth S, Roder B, Schnurpfeil G (1998) Singlet oxygen quantum yields of different photosensitizers in polar solvents and micellar solutions. J Porphyrins Phthalocyanines 2:145–158
31.
Ozoemena K, Kutznetsova N, Nyokong T (2001) Photosensitized transformation of 4-chlorophenol in the presence of aggregated and non-aggregated metallophthalocyanines. J Photochem Photobiol A Chem 139:217–224
32.
Ferry-Forgues S, Lavabre D (1999) Are fluorescence quantum yields so tricky to measure? A demonstration using familiar stationery products. J Chem Educ 76:1260–1264
33.
Fu J, Li XY, Ng DKP, Wu C (2002) Encapsulation of phthalocyanines in biodegradable poly(sebacic anhydride) nanoparticles. Langmuir 18:3843–3847
34.
Strickler SJ, Berg RA (1962) Relationship between absorption intensity and fluorescence lifetime of molecules. J Chem Phys 37:814–822
35.
Kubát P, Mosinger J (1996) Photophysical properties of metal complexes of meso-tetrakis(4-sulphonatophenyl)porphyrin. J Photochem Photobiol A Chem 96:93–97
36.
Seotsanyana-Mokhosi I, Chen JY, Nyokong T (2005) Synthesis, photophysicochemical studies of adjacently tetrasubstituted binaphthalo-phthalocyanines. J Porphyrins Phthalocyanines 9:316–325
37.
Ogunsipe A, Nyokong T (2005) Effects of central metal on the photophysical and photochemical properties of non-transition metal sulfophthalocyanine. J Porphyrins Phthalocyanines 9:121–129
38.
Ogunsipe A, Nyokong T (2005) Photophysical and photochemical studies of sulphonated non-transition metal phthalocyanines in aqueous and non-aqueous media. J Photochem Photobiol A Chem 173:211–220
39.
Ogunsipe A, Nyokong T (2005) Photophysicochemical consequences of bovine serum albumin binding to non-transition metal phthalocyanine sulfonates. Photochem Photobiol Sci 4:510–516
40.
Kaneko Y, Nishimura Y, Takane N, Arai T, Sakuragi H, Kobayashi N, Matsuhaga PC, Tokumaru K (1997) Violet emission observed from phthalocyanines. J Photochem Photobiol A Chem 106:177–183
41.
Darwent JR, Douglas P, Harriman A, Poter G, Richoux M (1982) Metal phthalocyanines and porphyrins as photosensitizers for reduction of water to hydrogen. Coord Chem Rev 44:83–126
42.
Kuznetsova NA, Gretsova NS, Derkacheva VM, Kaliya OL, Lukyanets EA (2003) Sulfonated phthalocyanines: aggregation and singlet oxygen quantum yield in aqueous solutions. J Porphyrins Phthalocyanines 7:147–154
43.
Grofcsik A, Baranyai P, Bitter I, Csokai V, Kubinyi M, Szegletes K, Tatai J, Vidóczy T (2004) Triple state properties of tetrasubstituted zinc phthalocyanine derivatives. J Mol Struct 704:11–15
44.
Ogunbayo TB, Nyokong T (2010) Photophysical and photochemical properties of Ni(II), Pd(II) and Pt(II) aryloxo and alkylthio derivatised phthalocyanine. J Mol Struct 973:96–103
45.
Çamur M, Bulut M, Kandaz M, Güney O (2009) Synthesis, characterization and fluorescence behavior of new fluorescent probe phthalocyanines bearing coumarin substituents. Polyhedron 28:233–238
46.
Canlıca M, Nyokong T (2010) Synthesis and photophysical properties of 1,1′-binaphthol substituted phthalocyanines. Inorg Chim Acta 363:3384–3389
47.
Choi CF, Huang JD, Lo PC, Fong WP, Ng DKP (2008) Glycosylated zinc(II) phthalocyanines as efficient photosensitisers for photodynamic therapy. Synthesis, photophysical properties and in vitro photodynamic activity. Org Biomol Chem 6:2173–2181
48.
Swarts JC, Maree DM (2006) The observation of room temperature delayed fluorescence in various non-peripherally substituted phthalocyanines. J Porphyrins Phthalocyanines 11:613–617
49.
Choi CF, Tsang PT, Huang JD, Chan EYM, Ko WH, Fong WP, Ng DKP (2004) Synthesis and in vitro photodynamic activity of new hexadeca-carboxy phthalocyanines. Chem Commun 2004:2236–2237
50.
Topal SZ, Yuksel F, Gürek AG, Ertkin K, Yeniguel B, Ahsen V (2009) Spectroscopic probing of acid–base properties and photocharacterization of phthalocyanines in organic solvents and polymer matrices. J Photochem Photobiol A Chem 202:205–213
51.
Makarov S, Litwinski C, Ermilov EA, Suvorova O, Röder B, Wöhrle D (2006) Synthesis and photophysical properties of annulated dinuclear and trinuclear phthalocyanines. Chem Eur J 12:1468–1474
52.
Seotsanyana-Mokhosi I, Nyokong T (2005) Photophysical properties of a water-soluble adjacently substituted bisnaphthalophthalocyanine. J Porphyrins Phthalocyanines 9:476–483
53.
Nombona N, Chidawanyika W, Nyokong T (2011) Photophysical behaviour of asymmetrically substituted metal free, Mg and Zn phthalocyanines in the presence of folic acid. Polyhedron 30:654–659
54.
Gilat SL, Ebbeseb TW (1993) Photophysics of lithium phthalocyanines and their radicals. J Phys Chem 97:3551–3554
55.
Tau P, Nyokong T (2007) Comparative photocatalytic efficiency of oxotitanium(IV) ­phthalocyanines for the oxidation of 1-hexene. J Mol Cat A Chem 273:149–155
56.
Tau P, Nyokong T (2006) Synthesis, electrochemical and photophysical properties of phthalocyaninato oxotitanium(IV) complexes tetra-substituted at the α and β positions with arylthio groups. Dalton Trans 2006:4482–4490
57.
Erdoğmuş A, Nyokong T (2009) Synthesis, photophysical and photochemical properties of novel soluble tetra[4-(thiophen-3yl)-phenoxy]phthalocyaninato zinc(II) and Ti(IV)O complexes. Inorg Chim Acta 362:4875–4883
58.
Atilla D, Durmuş M, Yılmaz Ö, Gürek AG, Ahsen V, Nyokong T (2007) Synthesis, photophysical and photochemical properties of poly(oxyethylene)-substituted phthalocyaninato oxotitanium(IV) complexes. Eur J Inorg Chem 2007:3573–3581
59.
Tau P, Nyokong T (2006) Synthesis and photophysical properties of octa-substituted phthalocyaninato oxotitanium(IV) derivatives. J Porphyrins Phthalocyanines 10:1040–1048
60.
Erdoğmus A, Durmuş M, Ugur AL, Avciata O, Avciata U, Nyokong T (2010) Synthesis, photophysics, photochemistry and fluorescence quenching studies on highly soluble substituted oxo-titanium(IV) phthalocyanine complexes. Synth Met 160:1868–1876
61.
Masilela N, Nyokong T (2010) The synthesis and photophysical properties of novel cationic tetra pyridiloxy substituted aluminium, silicon and titanium phthalocyanines in water. J Lumin 130:1787–1793
62.
Masilela N, Idowu M, Nyokong T (2009) Photophysical, photochemical and electrochemical properties of water soluble silicon, titanium and zinc phthalocyanines. J Photochem Photobiol A Chem 201:91–97
63.
Tau P, Nyokong T (2007) Spectroscopic characterisation and interactions of sulfonated titanium and tantalum phthalocyanines with methyl viologen. Inorg Chim Acta 360:2615–2622
64.
Tretyakova IN, Chemii VY, Tomachynski LA, Volkov SV (2007) Synthesis and luminescent properties of new zirconium(IV) and hafnium(IV) phthalocyanines with various carbonic acids as out-planed ligands. Dyes Pigm 75:67–72
65.
Bishop SM, Beeby A, Parker AW, Foley MSC, Philips D (1995) The preparation and photophysical measurement of perdeutero zinc phthalocyanine. J Photochem Photobiol A Chem 90:39–44
66.
Kuznetsova N, Gretsova N, Kalmykova E, Makarova E, Dashkevich S, Negrimovskii V, Kaliya O, Luk’yanets E (2000) Relationship between the photochemical properties and structure of pophyrins and related compounds. Russ J Gen Chem 70:133–140
67.
Gürol I, Durmuş M, Ahsen V, Nyokong T (2007) Synthesis, photophysical and photochemical properties of substituted zinc phthalocyanines. Dalton Trans 2007:3782–3791
68.
Zhang X, Xu H (1993) Influence of halogenation and aggregation on photosensitizing properties of zinc phthalocyanine (ZnPc). J Chem Soc Faraday Trans 89:3347–3351
69.
Ogunsipe A, Durmuş M, Atilla D, Gürek AG, Ahsen V, Nyokong T (2008) Synthesis, photophysical and photochemical studies on long chain zinc phthalocyanine derivatives. Synth Met 158:839–847
70.
Łapok L, Schnurpfeil G, Gerdes R, Gorun SM, Suvorova O, Kudryavtseva GS, Wöhrle D (2009) Synthesis of charged triazatetrabenzcorroles, phthalocyanines and tetrapyridylporphyrin, and their activities in the co-sensitized photooxidation of 2-mercaptoethanol. J Porphyrins Phthalocyanines 13:346–357
71.
Li H, Jensen TJ, Fronczek FR, Vicente MGH (2008) Syntheses and properties of a series of cationic water-soluble phthalocyanines. J Med Chem 51:502–511
72.
Beveridge AC, Bench BA, Gorun SM, Diebold GJ (2003) Evaluation of photodynamic therapy agents through transient grating measurements. J Phys Chem A 107:5138–5143
73.
Idowu M, Nyokong T (2009) Interaction of water-soluble CdTe quantum dots with octacarboxy metallophthalocyanines: a photophysical and photochemical study. J Lumin 129:356–362
74.
Idowu M, Nyokong T (2008) Photosensitizing properties of octacarboxy metallophthalocyanines in aqueous medium and their interaction with bovine serum albumin. J Photochem Photobiol A Chem 200:396–401
75.
Matlaba P, Nyokong T (2002) Synthesis, electrochemical and photochemical properties of unsymmetrically substituted zinc phthalocyanine complexes. Polyhedron 21:2463–2472
76.
Maree S, Nyokong T (2001) Syntheses and photochemical properties of octasubstituted ­phthalocyaninato zinc complexes. J Porphyrins Phthalocyanines 5:782–792
77.
Ke MR, Huang JD, Weng SM (2009) Comparison between non-peripherally and peripherally tetra-substituted zinc (II) phthalocyanines as photosensitizers: Synthesis, spectroscopic, photochemical and photobiological properties. J Photochem Photobiol A Chem 201:23–31
78.
Nishida M, Momotake A, Shinohara Y, Nishimura Y, Arai T (2007) Synthesis and photophysical properties of water-soluble dendrimers bearing a phthalocyanine core. J Porphyrins Phthalocyanines 11:448–454
79.
Erdoğmuş A, Nyokong T (2010) Synthesis of zinc phthalocyanine derivatives with improved photophysicochemical properties in aqueous media. J Mol Struct 977:26–38
80.
Erdoğmuş A, Moeno S, Litwinski C, Nyokong T (2010) Photophysical properties of newly synthesized fluorinated zinc phthalocyanines in the presence of CdTe quantum dots and the accompanying energy transfer processes. J Photochem Photobiol A Chem 210:200–208
81.
Bıyıklıoğlu Z, Durmuş M, Kantekin H (2010) Synthesis, photophysical and photochemical properties of quinoline substituted zinc (II) phthalocyanines and their quaternized derivatives. J Photochem Photobiol A Chem 211:32–41
82.
Erdoğmuş A, Ogunsipe A, Nyokong T (2009) Synthesis, photophysics and photochemistry of novel tetra(quinoxalinyl)phthalocyaninato zinc(II) complexes. J Photochem Photobiol A Chem 205:12–18
83.
Erdoğmuş A, Nyokong T (2010) Novel, soluble, FluXoro functional substituted zinc phthalocyanines; synthesis, characterization and photophysicochemical properties. Dyes Pigm 86:174–181
84.
Akpe V, Brismar H, Nyokong T, Osadebe PO (2010) Photophysical and photochemical parameters of octakis (benzylthio) phthalocyaninato zinc, aluminium and tin: red shift index concept in solvent effect on the ground state absorption of zinc phthalocyanine derivatives. J Mol Struct 984:1–14
85.
Liu JY, Jiang XJ, Fong WP, Ng DKP (2008) Highly photocytotoxic 1,4-dipegylated zinc(II) phthalocyanines. Effects of the chain length on the in vitro photodynamic activities. Org Biomol Chem 6:4560–4566
86.
Liu JY, Lo PC, Fong WP, Ng DKP (2009) Effects of the number and position of the substituents on the in vitro photodynamic activities of glucosylated zinc(II) phthalocyanines. Org Biomol Chem 7:1583–1591
87.
Seotsanyana-Mokhosi I, Nyokong T (2004) Synthesis and photochemical studies of substituted adjacent binaphthalophthalocyanines. J Porphyrins Phthalocyanines 4:1214–1221
88.
Seotsanyana-Mokhosi I, Nyokong T (2003) Photochemical studies of binuclear phenoxysubstituted phthalocyanines containing catecholate bridges. J Porphyrins Phthalocyanines 7:167–175
89.
Bishop M, Beeby A, Meunier H, Parker AW, Foley MSC, Phillips D (1996) The photophysics of disulfonated metallophthalocyanines upon complexation with fluoride. J Chem Soc Faraday Trans 92:2689–2695
90.
Siejak A, Wrobel D, Siejak P, Olejarz B, Ion RM (2009) Spectroscopic and photoelectric investigations of resonance effects in selected sulfonated phthalocyanines. Dyes Pigm 83:281–290
91.
Lang K, Wagnerová DM, Engst P, Kubát P (1994) Quenching of the triplet-state of metallophthalocyanines by dioxygen in the presence of bovine serum-albumin. Z Phys Chem 187:213–221
92.
Owens JW, Robins M (2001) Phthalocyanine photophysics and photosensitizer efficiency on human embryonic lung fibroblasts. J Porphyrins Phthalocyanines 5:460–464
93.
Idowu M, Nyokong T (2009) Study of the photophysical behavior of tetrasulfonated metallophthalocyanines in the presence of CdTe quantum dots. Polyhedron 28:891–896
94.
Idowu M, Nyokong T (2009) Synthesis, photophysical and photochemical studies of water soluble cationic zinc phthalocyanine derivatives. Polyhedron 28:416–424
95.
Segalla A, Borsarelli CD, Braslavsky SE, Spikes JD, Roncucci G, Dei D, Chiti G, Jori G, Reddi E (2002) Photophysical, photochemical and antibacterial photosensitizing properties of a novel octacationic Zn(II)-phthalocyanine. Photochem Photobiol Sci 1:641–648
96.
Lo PC, Zhao B, Duan W, Fong WP, Ko WH, Ng DKP (2007) Synthesis and in vitro ­photodynamic activity of mono-substituted amphiphilic zinc(II) phthalocyanines. Bioorg Med Chem Lett 17:1073–1077
97.
Makarov DA, Yuzhakova OA, Silvika LK, Kuznetsova N, Negrimovsky VM, Kaliya O, Lukyanets EA (2007) Cationic Zn and Al phthalocyanines: synthesis, spectroscopy and photosensitizing properties. J Porphyrins Phthalocyanines 11:586–595
98.
Strassert CA, Bilmes GM, Awruch J, Dicello LE (2008) Comparative photophysical investigation of oxygen and sulfur as covalent linkers on octaalkylamino substituted zinc(II) phthalocyanines. Photochem Photobiol Sci 7:738–747
99.
Duan W, Lo PC, Duan L, Fong WP, Ng DKP (2010) Preparation and in vitro photodynamic activity of amphiphilic zinc(II) phthalocyanines substituted with 2-(dimethylamino)ethylthio moieties and their N-alkylated derivatives. Bioorg Med Chem Lett 18:2672–2677
100.
Dupouy EA, Lazzeri D, Durantini EN (2004) Photodynamic activity of cationic and non-charged Zn(II) tetrapyridinoporphyrazine derivatives: biological consequences in human erythrocytes and Escherichia coli. Photochem Photobiol Sci 3:992–998
101.
Marti C, Nonell S, Nicolau M, Torres T (2000) Photophysical properties of neutral and cationic tetrapyridinoporphyrazines. Photochem Photobiol 71:53–59
102.
Durmuş M, Nyokong T (2008) Photophysicochemical and fluorescence quenching studies of benzyloxyphenoxy-substituted zinc phthalocyanines. Spectrochim Acta A 69:1170–1177
103.
Durmuş M, Ahsen V, Nyokong T (2007) Photophysical and photochemical studies of long chain-substituted zinc phthalocyanines. J Photochem Photobiol A Chem 186:323–329
104.
Li H, Nguyen N, Fronczek FR, Vicente MGH (2009) Syntheses and properties of octa-, tetra-, and di-hydroxy-substituted phthalocyanines. Tetrahedron 65:3357–3363
105.
Gürol İ, Durmuş M, Ahsen V (2010) Photophysical and photochemical properties of fluorinated and non-fluorinated n-propanol-substituted zinc phthalocyanines. Eur J Inorg Chem 2010:1220–1230
106.
Shinohara H, Tsaryova O, Schnurpfeil G, Wöhrle D (2006) Differently substituted phthalocyanines: comparison of calculated energy levels, singlet oxygen quantum yields, photo-oxidative stabilities, photocatalytic and catalytic activities. J Photochem Photobiol A Chem 184:50–57
107.
Chidawanyika W, Ogunsipe A, Nyokong T (2007) Syntheses and photophysics of new phthalocyanine derivatives of zinc, cadmium and mercury. New J Chem 31:377–384
108.
Moeno S, Nyokong T (2009) Opposing responses elicited by positively charged phthalocyanines in the presence of CdTe quantum dots. J Photochem Photobiol A Chem 201:228–236
109.
Durmuş M, Yaman H, Göl C, Ahsen V, Nyokong T (2011) New water-soluble zinc phthalocyanines: synthesis, photophysical, photochemical and bovine serum albumin binding properties. Dyes Pigm 91:153–163
110.
Saydan N, Durmuş M, Dizge MG, Yaman H, Gürek AG, Antunes E, Nyokong T, Ahsen V (2009) Water soluble phthalocyanines mediated photodynamic effect on mesothelioma cells. J Porphyrins Phthalocyanines 13:681–690
111.
Chidawanyika W, Nyokong T (2009) The synthesis and photophysicochemical pro­perties of low-symmetry zinc phthalocyanine analogues. J Photochem Photobiol A Chem 206:169–176
112.
Tau P, Ogunsipe AO, Maree S, Maree MD, Nyokong T (2003) Influence of cyclodextrins on the fluorescence, photostability and singlet oxygen quantum yields of zinc phthalocyanine and naphthalocyanine complexes. J Porphyrins Phthalocyanines 7:439–446
113.
Ogunsipe AO, Nyokong T (2004) Effects of substituents and solvents on the photochemical properties of zinc phthalocyanine complexes and their protonated derivatives. J Mol Struct 689:89–97
114.
Atilla D, Saydan N, Durmuş M, Gürek AG, Khan T, Rück A, Walt H, Nyokong T, Ahsen V (2007) Synthesis and photodynamic potential of tetra- and octa-triethyleneoxysulfonyl substituted zinc phthalocyanines. J Photochem Photobiol A Chem 186:298–307
115.
Tuncel S, Dumoulin F, Gailer J, Sooriyaarachchi M, Atilla D, Durmuş M, Bouchu D, Savoie H, Boyle RW, Ahsen V (2011) A set of highly water-soluble tetraethyleneglycol-substituted Zn(II) phthalocyanines: synthesis, photochemical and photophysical properties, interaction with plasma proteins and in vitro phototoxicity. Dalton Trans. doi:10.​1039/​c0dt01260b
116.
FitzGerald S, Farren C, Stanley CF, Beeby A, Bryce MR (2002) Fluorescent phthalocyanine dimers – a steady state and flash photolysis study. Photochem Photobiol Sci 1:581–587
117.
Zhao Z, Ogunsipe AO, Maree MD, Nyokong T (2005) Synthesis and photophysical properties of a covalently linked porphyrin-phthalocyanine conjugate. J Porphyrins Phthalocyanines 9:186–197
118.
Yslas EI, Rivarola V, Durantini EN (2004) Synthesis and photodynamic activity of zinc(II) phthalocyanine derivatives bearing methoxy and trifluoromethylbenzyloxy substituents in homogeneous and biological media. Bioorg Med Chem 13:39–46
119.
Cormick MP, Rovera M, Durantini EN (2008) Synthesis, spectroscopic properties and photodynamic activity of a novel Zn(II) phthalocyanine substituted by fluconazole groups. J Photochem Photobiol A Chem 194:220–229
120.
Beeby A, FitzGerald S, Stanley CF (2001) A photophysical study of protonated (tetra-tert-butylphthalocyaninato) zinc. J Chem Soc Perkin Trans 2:1978–1982
121.
Ozoemena K, Nyokong T (2003) Synthesis, spectroscopy and photochemistry of octasubstituted thiol-derivatized phthalocyaninatozinc(II) complexes. Inorg Chem Commun 6:1192–1195
122.
Hone DC, Walker PI, Evans-Gowing R, FitzGerald S, Beeby A, Chambrier I, Cook MJ, Russell DA (2002) Generation of cytotoxic singlet oxygen via phthalocyanine-stabilized gold nanoparticles: a potential delivery vehicle for photodynamic therapy. Langmuir 18:2985–2987
123.
Kaestner L, Cesson M, Kassab K, Christensen T, Edminson PD, Cook MJ, Chambrier I, Jori G (2003) Zinc octa-n-alkyl phthalocyanines in photodynamic therapy: photophysical properties, accumulation and apoptosis in cell cultures, studies in erythrocytes and topical application to Balb/c mice skin. Photochem Photobiol Sci 2:660–667
124.
Al-Raqa SY (2006) Synthesis, photochemical and photophysical properties of novel unsymmetrically substituted zinc(II) phthalocyanines. J Porphyrins Phthalocyanines 10:55–62
125.
Khene S, Cammidge AN, Cook MJ, Nyokong T (2007) Electrochemical and photophysical characterization of nonperipherally-octaalkyl substituted dichlorotin(IV) phthalocyanine and tetrabenzotriazaporphyrin compounds. J Porphyrins Phthalocyanines 11:761–770
126.
Makarov SG, Suvorova O, Litwinski C, Ermilov EA, Roeder B, Tsaryova O, Dülcks T, Wöhrle D (2007) Linear and rectangular trinuclear phthalocyanines. Eur J Inorg Chem 2007:546–552
127.
Chidawanyika W, Nyokong T (2009) Spectroscopic and photophysicochemical behaviour of novel cadmium phthalocyanine derivatives tetra-substituted at the alpha and beta positions. J Photochem Photobiol A Chem 202:99–106
128.
Chidawanyika W, Antunes E, Nyokong T (2008) Synthesis and solvent effects on the photophysicochemical properties of novel cadmium phenoxy phthalocyanines. J Photochem Photobiol A Chem 195:183–190
129.
Yanık H, Aydın D, Durmuş M, Ahsen V (2009) Peripheral and non-peripheral tetra substituted aluminium, gallium and indium phthalocyanines: synthesis, photophysics and photochemistry. J Photochem Photobiol A Chem 206:18–26
130.
Brannon JH, Magde D (1980) Picosecond laser photophysics. Group 3A phthalocyanines. J Am Chem Soc 102:62–65
131.
Simpson MSC, Beeby A, Bishop SM, MacRobert AJ, Parker AW, Phillips D (1992) Time-resolved spectroscopic studies of sulphonated aluminium phthalocyanine triplet states. Proc SPIE 1640:520–529
132.
Oldham TC, Eigenbrot IV, Crystal B, Phillips D (1996) Photophysics of photosensitizing dyes in living cell suspensions. Proc SPIE 2625:266–277
133.
Foley MSC, Beeby A, Parker AW, Bishop SM, Phillips D (1997) Excited triplet state photophysics of the sulphonated aluminium phthalocyanines bound to human serum albumin. J Photochem Photobiol B Biol 38:10–17
134.
Beeby A, Parker AW, Simpson MSC, Phillips D (1992) The effect of solvent deuteration on the photophysics of sulphonated aluminium phthalocyanine. J Photochem Photobiol B Biol 16:73–81
135.
Lacey JA, Phillips D, Milgrom LR, Yahioglu G, Rees RD (1998) Photophysical studies of some 5,10,15,20-tetraarylethynylporphyrinatozinc(II) complexes as potential lead compounds for photodynamic therapy. Photochem Photobiol 67:97–100
136.
Idowu M, Chen JY, Nyokong T (2008) Photoinduced energy transfer between water-soluble CdTe quantum dots and aluminium tetrasulfonated phthalocyanine. New J Chem 32:290–296
137.
Durmuş M, Nyokong T (2007) Synthesis, photophysical and photochemical properties of tetra and octa-substituted gallium and indium phthalocyanines. Polyhedron 26:3323–3335
138.
Masilela N, Nyokong T (2010) The synthesis and photophysical properties of water soluble tetrasulfonated, octacarboxylated and quaternised 2, (3)-tetra-(2 pyridiloxy) Ga phthalocyanines. Dyes Pigm 84:242–248
139.
Durmuş M, Nyokong T (2007) The synthesis, fluorescence behaviour and singlet oxygen studies of new water-soluble cationic gallium(III) phthalocyanines. Inorg Chem Commun 10:333–338
140.
Ogunsipe A, Nyokong T, Durmuş M (2007) Photophysical, photochemical and bovine serum albumin binding studies on water-soluble gallium(III) phthalocyanine derivatives. J Porphyrins Phthalocyanines 11:635–644
141.
Çamur M, Ahsen V, Durmuş M (2011) The first comparison of photophysical and photochemical properties of non-ionic, ionic and zwitterionic gallium (III) and indium (III) phthalocyanines. J Photochem Photobiol A Chem 219:217–227
142.
Durmuş M, Nyokong T (2007) Synthesis, photophysical and photochemical properties of aryloxy tetra-substituted gallium and indium phthalocyanine derivatives. Tetrahedron 63:1385–1394
143.
Chauke V, Nyokong T (2008) Photocatalytic oxidation of 1-hexene using GaPc and InPc octasubstituted derivatives. J Mol Catal A Chem 289:9–13
144.
Moeno S, Nyokong T (2009) Solvent and central metal effects on the photophysical and photochemical properties of peripherally tetra mercaptopyridine substituted metallophthalocyanines. J Photochem Photobiol A Chem 203:204–210
145.
Durmuş M, Ahsen V (2010) Water-soluble cationic gallium and indium phthalocyanines for photodynamic therapy. J Inorg Biochem 104:297–309
146.
Chauke V, Ogunsipe A, Durmuş M, Nyokong T (2007) Novel gallium(III) phthalocyanine derivatives–synthesis, photophysics and photochemistry. Polyhedron 26:2663–2671
147.
Chen Y, Araki Y, Fujitsuka M, Hanack M, Ito O, O’Flaherty SM, Blau WJ (2004) Photophysical studies on axially substituted indium and gallium phthalocyanines upon UV–Vis laser irradiation. Solid State Commun 131:773–778
148.
Chen Y, Hanack M, Araki Y, Ito O (2005) Axially modified gallium phthalocyanines and naphthalocyanines for optical limiting. Chem Soc Rev 34:517–529
149.
Chen Y, O’Flaherty S, Fujitsuka M, Hanack M, Subramanian LR, Ito O, Blau WJ (2002) Synthesis, characterization, and optical-limiting properties of axially substituted gallium(III) naphthalocyanines. Chem Mater 14:5163–5168
150.
Durmuş M, Nyokong T (2007) Synthesis, photophysical and photochemical studies of new water-soluble indium(III) phthalocyanines. Photochem Photobiol Sci 6:659–668
151.
Durmuş M, Erdoğmuş A, Ogunsipe A, Nyokong T (2009) The synthesis and photophysicochemical behaviour of novel water-soluble cationic indium(III) phthalocyanine. Dyes Pigm 82:244–250
152.
Chauke V, Durmuş M, Nyokong T (2007) Photochemistry, photophysics and nonlinear optical parameters of phenoxy and tert-butylphenoxy substituted indium(III) phthalocyanines. J Photochem Photobiol A Chem 192:179–187
153.
Li YS, Zaidi SIA, Rodgers MAJ, Mukhtar H, Kenney ME, Oleinick NL, He J, Hedy E, Larkin HE, Rihter BD (1997) The synthesis, photophysical and photobiological properties and in vitro structure-activity relationships of a set of silicon phthalocyanine pdt photosensitizers. Photochem Photobiol 65:581–586
154.
Jiang XJ, Yeung SL, Lo PC, Fong WP, Ng DKP (2011) Phthalocyanine-polyamine conjugates as highly efficient photosensitizers for photodynamic therapy. J Med Chem 54:320–330
155.
Jiang XJ, Lo PC, Yeung SL, Fong WP, Ng DKP (2010) A pH-responsive fluorescence probe and photosensitiser based on a tetraamino silicon(IV) phthalocyanine. Chem Commun 46:3188–3190
156.
Lo PC, Huang JD, Cheng DYY, Chan EYM, Fong WP, Ko WH, Ng DKP (2004) New amphiphilic silicon(iv) phthalocyanines as efficient photosensitizers for photodynamic therapy: synthesis, photophysical properties, and in vitro photodynamic activities. Chem Eur J 10:4831–4838
157.
Lo PC, Chan CMH, Liu JY, Fong WP, Ng DKP (2007) Highly photocytotoxic glucosylated silicon(IV) phthalocyanines. Effects of peripheral chloro substitution on the photophysical and photodynamic properties. J Med Chem 50:2100–2107
158.
Farren C, FitzGerald S, Bryce MR, Beeby A, Batsanov AS (2002) Synthesis, structure and optical characterisation of silicon phthalocyanine bis-esters. J Chem Soc Perkin Trans 2:59–66
159.
Jiang XJ, Huang JD, Zhu YJ, Tang FX, Ng DKP, Sun JC (2006) Preparation and in vitro photodynamic activities of novel axially substituted silicon (IV) phthalocyanines and their bovine serum albumin conjugates. Bioorg Med Chem Lett 16:2450–2453
160.
Liu JY, Ermilov EA, Röder B, Ng DKP (2009) Switching the photo-induced energy and electron-transfer processes in BODIPY–phthalocyanine conjugates. Chem Commun 1517–1519
161.
Ermilov EA, Liu JY, Ng DKP, Röder B (2009) Spectroscopic study of electron and energy transfer in novel silicon phthalocyanine—boron dipyrromethene triads. Phys Chem Chem Phys 11:6430–6440
162.
Lee PPS, Lo PC, Chan EYM, Fong WP, Ko WH, Ng DKP (2005) Synthesis and in vitro photodynamic activity of novel galactose-containing phthalocyanines. Tetrahedron Lett 46:1551–1554
163.
Maree DM, Kuznetsova N, Nyokong T (2001) Silicon octaphenoxyphthalocyanines: photostability and singlet oxygen quantum yields. J Photochem Photobiol A Chem 140:117–125
164.
Huang JD, Wang S, Lo PC, Fong WP, Ko WH, Ng DKP (2004) Halogenated silicon(IV) phthalocyanines with axial poly(ethylene glycol) chains. Synthesis, spectroscopic properties, complexation with bovine serum albumin and in vitro photodynamic activities. New J Chem 28:348–354
165.
Lo PC, Wang S, Zeug A, Meyer M, Roder B, Ng DKP (2003) Preparation and photophysical properties of halogenated silicon(IV) phthalocyanines substituted axially with poly(ethylene glycol) chains. Tetrahedron Lett 44:1967–1970
166.
Idowu M, Nyokong T (2008) Photophysical and photochemical properties of tetrasulfonated silicon and germanium phthalocyanine in aqueous and non-aqueous media. J Photochem Photobiol A Chem 197:273–280
167.
Idowu M, Nyokong T (2009) Photophysicochemical and fluorescence quenching studies of tetra- and octa-carboxy substituted silicon and germanium phthalocyanines. J Photochem Photobiol A Chem 204:63–68
168.
Gunaratne T, Kennedy VO, Kenney ME, Rodgers MAJ (2004) Photophysics of octabutoxy phthalocyaninato-Ni(II) in toluene: ultrafast experiments and DFT/TDDFT studies. J Phys Chem A 108:2576–2582
169.
Idowu M, Nyokong T (2008) Synthesis, photophysics and photochemistry of tin(IV) phthalocyanine derivatives. J Photochem Photobiol A Chem 199:282–290
170.
Modibane D, Nyokong T (2008) Synthesis and photophysical properties of lead phthalocyanines. Polyhedron 27:1102–1110
171.
Modibane KD, Nyokong T (2009) Synthesis, photophysical and nonlinear optical properties of microwave synthesized 4-tetra and octa-substituted lead phthalocyanines. Polyhedron 28:1475–1480
172.
Modibane D, Nyokong T (2009) Synthesis, photophysical and photochemical properties of octa-substituted antimony phthalocyanines. Polyhedron 28:479–484
173.
Isago H, Miura K, Oyama Y (2008) Synthesis and properties of a highly soluble dihydoxo(tetra-tert-butylphthalocyaninato)antimony(V) complex as a precursor toward water-soluble phthalocyanines. J Inorg Biochem 102:380–387
174.
Antunes E, Nyokong T (2009) Synthesis and photophysical behavior of axially substituted phthalocyanine, tetrabenzotriazaporphyrin, and triazatetrabenzcorrole phosphorous complexes. J Porphyrins Phthalocyanines 13:153–160
175.
Gerhardt SA, Lewis JW, Zhang JZ, Bonnett R, McManus KA (2003) Photophysical behaviour of an opp-dibenzoporphyrin (2, 12-diethyl-3,13-dimethyldibenzo[g, q]porphyrin) in micelles and organic solvents. Photochem Photobiol Sci 2:934–938
176.
Nyokong T (2007) Effects of substituents on the photochemical and photophysical properties of main group metal phthalocyanines. Coord Chem Rev 251:1707–1722
177.
Stuzhin PA (1999) Azaporphyrins and phthalocyanines as multicentre conjugated ampholites. J Porphyrins Phthalocyanines 3:500–513
178.
Lukyanets EA (1999) Phthalocyanines as photosensitizers in the photodynamic therapy of cancer. J Porphyrins Phthalocyanines 3:424–432
179.
Daziano JP, Steenken S, Chabannon C, Mannoni P, Chanon M, Julliard M (1996) Photophysical and redox properties of a series of phthalocyanines: relation with their photodynamic activities on TF-1 and Daudi leukemic cells. Photochem Photobiol 64:712–719
180.
Tran Thi TH, Desforge C, Thiec C, Gaspard S (1989) Singlet-singlet and triplet-triplet intramolecular transfer processes in a covalently linked porphyrin-phthalocyanine heterodimer. J Phys Chem 93:1226–1233
181.
Mack J, Stillman MJ (2003) Electronic structures of metal phthalocyanine and porphyrin complexes from analysis of the UV-Visible absorption and magnetic circular dichroism spectra and molecular orbital calculations. In: Kadish KM, Smith KM, Guilard R (eds) The porphyrin handbook, vol 16. Academic Press, New York, pp 43–113
Metadata
Title
Photochemical and Photophysical Characterization
Author
Mahmut Durmuş
Copyright Year
2012
Publisher
Springer Netherlands
Book
Photosensitizers in Medicine, Environment, and Security

Print ISBN: 978-90-481-3870-8

Electronic ISBN: 978-90-481-3872-2

Copyright Year: 2012

DOI
https://doi.org/10.1007/978-90-481-3872-2_4