Citation: LIU Hong, ZHANG Lei, JIA Xiao, LIU Jian-Yong, XUE Jin-Ping. Synthesis and Photophysical/Photochemical Properties of Aryloxy Substituted Phthalocyanine Zinc Complex[J]. Chinese Journal of Inorganic Chemistry, ;2013, 29(3): 486-492. doi: 10.3969/j.issn.1001-4861.2013.00.062 shu

Synthesis and Photophysical/Photochemical Properties of Aryloxy Substituted Phthalocyanine Zinc Complex

1.
Fujian Engineering Research Center for Drug and Diagnoses-Treat of Photodynamic Therapy/College of Chemistry and Chemical Engineering, Fuzhou University, Fuzhou 350002, China

Received Date: 23 July 2012
Available Online: 25 September 2012
Fund Project: 国家科技部科技重大专项(No.2011ZX09101-001-04) (No.2011ZX09101-001-04)国家自然科学基金(No.21101028,No.21201035) (No.21101028,No.21201035)福建省科技厅重大项目 (No.2009Y2004) (No.2009Y2004)福建省自然科学基金(No.2012J05021) (No.2012J05021)福州大学科技发展基金(No.2011-XY-8)资助项目。 (No.2011-XY-8)

Four new substituted phthalonitriles such as 3-(5-aminonaphthoxy) phthalonitrile(C₁₈H₁₁N₃O), 4-(5-aminonaphthoxy) phthalonitrile(C₁₈H₁₁N₃O), 3-biphenyloxy-phthalonitrile(C₂₀H₁₂N₂O) and 4-biphenyloxy-phthalonitrile(C₂₀H₁₂N₂O) have been synthesized, which are converted into the corresponding phthalocyanine-zinc(Ⅱ) complexes with aryloxy substitunents:tetra-alpha-(5-aminonaphthoxy) phthalocyanines zinc(Ⅱ) (C₇₂H₄₄N₁₂O₄Zn), tetra-β-(5-aminonaphthoxy) phthalocyanines zinc(Ⅱ)(C₇₂H₄₄N₁₂O₄Zn), tetra-alpha-biphenyloxy-phthalocyanines zinc(Ⅱ)(C₈₀H₄₈N₈O₄Zn) and tetra-β-biphenyloxy-phthalocyanines zinc(Ⅱ)(C₈₀H₄₈N₈O₄Zn). Their maximum absorption wavelength, molar extinction coefficient, emission wavelength, fluorescence quantum yields (Ф_F), the singlet oxygen quantum yields(Φ_Δ), and photodegradation constant(k) have been measured by the UV-Vis absorption and fluorescence spectra. The structure-activity relationship have been discussed in comparision with their analogues. The results show that tetra-alpha-biphenyloxy-phthalocyanines zinc(Ⅱ) has large extinction coefficient in the red visible region of the light with relatively higher singlet oxygen quantum yield, it is a promising photosensitizer for use in photodynamic therapy.
- photodynamic therapy;substituted phthalocyanine;photophysical property;photochemical property
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