Synthesis and Study of Properties for Asymmetric Triphenylamine-Zinc Phthalocyanine

doi:10.6023/cjoc201206019

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (12): 2315-2321.DOI: 10.6023/cjoc201206019 Previous Articles Next Articles

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不对称三苯胺-锌酞菁的合成及性能研究

毛利军, 谭青龙, 辛冠琼, 韩明亮, 张学俊

中北大学理学院太原 030051

收稿日期:2012-06-19 修回日期:2012-08-01 发布日期:2012-08-10
通讯作者: 张学俊 E-mail:zhangxuejun@nuc.edu.cn
基金资助:
国家自然科学基金(No. 20871108)、山西省自然科学基金(No. 2011011022-4)资助项目.

Synthesis and Study of Properties for Asymmetric Triphenylamine-Zinc Phthalocyanine

Mao Lijun, Tan Qinglong, Xin Guanqiong, Han Mingliang, Zhang Xuejun

Department of Chemistry, College of Science, North University of China, Taiyuan 030051

Received:2012-06-19 Revised:2012-08-01 Published:2012-08-10
Supported by:
Project supported by the National Natural Science Foundation of China (No. 20871108) and the Natural Science Foundation of Shanxi Province (No. 2011011022-4).

Triphenylamine-zinc phthalocyanine (TQPc) that contains a bulky triphenylamine group and three 8-oxy-quinoline groups has been found to exhibit preferable performance. The first example of TQPc has been synthesized. Its zinc complexes of the well-known electron transport material displays enhanced electron-accepting ability relative to free- metallophthalocyanines, and can also be used as chemical sensors, liquid crystals, photodynamic therapy, data storage and non-linear optics. The triphenylamine-zinc phthalocyanine is synthesized by statistical condensation. The main chemicals are aminophenol, p-chloronitrobenzene, 8-hydroxyquinoline, 4-nitrophthalonitrile and zinc acetate. The fragment 4,4'-dinitro-4"-hydroxy- triphenylamine is synthesized by the reacting from aminophenol with p-chloronitrobenzene at the catalysis of anhydrous potassium carbonate. The gross yield is 27.5%, and its purity is 96.6%. In comparison with other methods, there are some advantages in this method: the materials are cheap and easily available, and the product can be used as a substituent for phthalocyanine. All compounds are characterized by ¹H NMR, IR spectra and elemental analysis. The electronic spectra of TQPc exhibits an intense π-π* transition of triphenylamine unit identity together with characteristic B bands of the phthalocyanine core. Energy transfer through oxy bridges has been confirmed by ultraviolet irradiation of triphenylamine. The aggregative behavior is studied in DMF and CH₂Cl₂. The results indicate that it is not aggregative in DMF, whereas forms dimer in CH₂Cl₂ at 0.223×10^-5～2.587×10^-5 mol/L. The equilibrium constant for the dimer is calculated at the same time, indicating that the less polar solvent is unfavorable for the presence of the monomer. The redox behavior is studied by cyclic voltammetry. Its level structure of energy band is calculated by cyclic voltammetry combined with differential voltammograms, this molecule has been found to have a low LUMO (-1.04 V vs SCE) and a deep HOMO (0.78 V vs SCE) energy level. The results indicate that it matches with the energy level of the nanocrystalline of TiO₂, and is thus very promising as an electron transport material for dye-sensitized solar cells.

Key words: phthalocyanine, 8-hydroxyquinoline, triphenylamine, photosensitive dyes, dimer

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Mao Lijun, Tan Qinglong, Xin Guanqiong, Han Mingliang, Zhang Xuejun. Synthesis and Study of Properties for Asymmetric Triphenylamine-Zinc Phthalocyanine[J]. Chin. J. Org. Chem., 2012, 32(12): 2315-2321.

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不对称三苯胺-锌酞菁的合成及性能研究

Synthesis and Study of Properties for Asymmetric Triphenylamine-Zinc Phthalocyanine

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