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芳氧基取代酞菁锌的合成及光物理化学性质

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

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【作者】 刘宏张磊贾潇刘见永薛金萍

【Author】 LIU Hong ZHANG Lei JIA Xiao LIU Jian-Yong XUE Jin-Ping(Fujian Engineering Research Center for Drug and Diagnoses-Treat of Photodynamic Therapy/College of Chemistry and Chemical Engineering,Fuzhou University,Fuzhou 350002,China)

【机构】 福建省光动力治疗药物与诊疗工程技术研究中心,福州大学化学化工学院

【摘要】 合成得到3-(5-氨基-萘氧基)邻苯二甲腈(C18H11N3O)、4-(5-氨基-萘氧基)邻苯二甲腈(C18H11N3O)、3-联苯氧基邻苯二甲腈(C20H12N2O)及4-联苯氧基邻苯二甲腈(C20H12N2O)4种未见报导的取代邻苯二甲腈,以此为前躯体合成了四[α-(5-氨基-萘氧基)]酞菁锌(C72H44N12O4Zn)、四[β-(5-氨基-萘氧基)]酞菁锌(C72H44N12O4Zn)、四[α-(联苯氧基)]酞菁锌(C80H48N8O4Zn)和四[β-(联苯氧基)]酞菁锌(C80H48N8O4Zn)4种未见报导的芳氧基取代酞菁锌配合物。通过测定它们的紫外-可见吸收光谱、荧光发射光谱,获得其最大吸收波长及其摩尔消光系数、最大发射波长、荧光量子产率(ΦF)、单线态氧量子产率(ΦΔ)及光降解速率常数并与其类似物进行了比较,探讨了它们的光物理光化学性质的构效关系。研究结果表明四[α-(联苯氧基)]酞菁锌在红光区具有大的摩尔消光系数,且具有较高的ΦΔ,有望开发成为光动力治疗用光敏剂。

【Abstract】 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)(C72H44 N12O4Zn),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.

【基金】 国家科技部科技重大专项(No.2011ZX09101-001-04);国家自然科学基金(No.21101028,No.21201035);福建省科技厅重大项目(No.2009Y2004);福建省自然科学基金(No.2012J05021);福州大学科技发展基金(No.2011-XY-8)资助项目
  • 【文献出处】 无机化学学报 ,Chinese Journal of Inorganic Chemistry , 编辑部邮箱 ,2013年03期
  • 【分类号】O627.23
  • 【被引频次】11
  • 【下载频次】311
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