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
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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 (ФF), the singlet oxygen quantum yields(ΦΔ), 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.
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