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. 2014:2014:952632.
doi: 10.1155/2014/952632. Epub 2014 Sep 11.

Effect of Some Substituents Increasing the Solubility of Zn(II) and Al(III) Phthalocyanines on Their Photophysical Properties

A A Chernonosov  1 , E A Ermilov  2 , B Röder  2 , L I Solovyova  3 , O S Fedorova  1
Affiliations

Effect of Some Substituents Increasing the Solubility of Zn(II) and Al(III) Phthalocyanines on Their Photophysical Properties

A A Chernonosov et al. Bioinorg Chem Appl. 2014.

Abstract

Water solubility of phthalocyanines (Pcs) usually increases by the introduction of charged or carboxy substituents in the peripheral positions of the macrocycle. As a result, such structural changes influence their photophysical and photochemical properties as photosensitizers. Phthalocyanines substituted with four or eight terminal carboxyl groups and having in some cases additional eight positive charges (water soluble phthalocyanines) were studied in order to evaluate the spectroscopic and photophysical effects of these side residues on the chromophore properties. The quantum yield of singlet oxygen ((1)O2) generation, the triplet-triplet absorption, and the transient absorption spectra were measured and linked to the structure of the substituents. It was shown that charged substituents did not change the quantum yields of (1)O2 generation but decrease its lifetimes. The introduction of the charged substituents not only increases the water solubility but also significantly changes absorption, fluorescence, and transient absorption spectra of water soluble Pcs.

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Figures

Figure 1
Figure 1
Structures of the Pc complexes 1–4.
Figure 2
Figure 2
Normalized absorption spectra of the compounds containing PcZn(II) 2, 4 (a) and PcAl(III) 1, 3 (b). Normalized fluorescence spectra of the compounds containing PcZn(II) 2, 4 (c) and PcAl(III) 1, 3 (d).
Figure 3
Figure 3
Evolution-associated difference spectra that result from a global analysis on transient absorption experiments on compounds containing 2 and 4.
See this image and copyright information in PMC

References

    1. Ali H, van Lier JE. Porphyrins and phthalocyanines as photosensitizers and radiosensitizers. In: Kadish KM, Smith KM, Guilard R, editors. Handbook of Porphyrin Science with Applications to Chemistry, Physics, Materials Science, Engineering, Biology and Medicine. Singapore: World Scientific; 2010.
    1. Lukyanets EA. Phthalocyanines as photosensitizers in the photodynamic therapy of cancer. Journal of Porphyrins and Phthalocyanines. 1999;3(6-7):424–432.
    1. Bonnett R. Chemical Aspects of Photodynamic Therapy. Amsterdam, The Netherlands: Gordon and Breach Science Publishers; 2000.
    1. Levy JG. Photosensitizers in photodynamic therapy. Seminars in Oncology. 1994;21(6) supplemen 15:4–10. - PubMed
    1. Langlois R, Ali H, Brasseur N, Wagner JR, van Lier JE. Biological activities of phythalocyanines—IV. Type II sensitized photooxidation of L-tryptophan and cholesterol by sulfonated metallo phthalocyanines. Photochemistry and photobiology. 1986;44(2):117–123. - PubMed

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