有机化学 ›› 2016, Vol. 36 ›› Issue (1): 213-217.DOI: 10.6023/cjoc201508013 上一篇    下一篇

研究简报

萘氧桥香豆素-双核锌酞菁的合成与性能研究

曹杰, 廖超强, 杨玲, 张学俊   

  1. 中北大学理学院 太原 030051
  • 收稿日期:2015-08-11 修回日期:2015-09-02 出版日期:2016-01-25 发布日期:2015-09-15
  • 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. 51272239)、山西省自然科学基金(No. 2015011011)和山西省回国留学人员科研(No. 2015-078)资助项目.

Synthesis and Characterization of the Coumarin-Binuclear Zinc Phthalocyanine Formed by Droxynaphthyl Bridge

Cao Jie, Liao Chaoqiang, Yang Ling, Zhang Xuejun   

  1. College of Science, North University of China, Taiyuan 030051
  • Received:2015-08-11 Revised:2015-09-02 Online:2016-01-25 Published:2015-09-15
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 51272239), the National Natural Science Foundation of Shanxi Province (No. 2015011011) and the Shanxi Scholarship Council of China (No. 2015-078).

以1,5-二羟基萘、4-硝基邻苯二甲腈、间苯二酚、乙酰乙酸乙酯以及醋酸锌为主要原料, 合成了9(10),16(17),23(24)-三[4-甲基-7-香豆素氧基]-2(3)-(1,5-二氧基萘)双核锌酞菁(bi-CPc). 利用1H NMR、FT-IR、UV-Vis、元素分析、热重分析等手段对前驱体和bi-CPc的结构和性能进行 表征. 结果表明, bi-CPc的紫外可见吸收光谱表现出强烈的π-π*跃迁且在N,N-二甲基甲酰胺(DMF)溶液中以单体形式存在, 并且具有良好的热稳定性. 用循环伏安法研究了bi-CPc的氧化还原行为, 计算其LUMO和HOMO能级与纳米TiO2能级匹配. 通过进一步结构修饰, 有望作为性能良好的光敏染料用于太阳能电池.

关键词: 酞菁, 双核, 香豆素, 染料敏化太阳能电池

9(10),16(17),23(24)-Tris[4-methyl-coumarin-7-yloxy]-2(3)-(1,5-naphthalene) binuclear zinc phthalocyanine (bi-CPc) based 1,5-dihydroxynaphthalene, 4-nitro-phthalonitrile, resorcinol, ethyl acetoacetate and zinc acetate on raw material was synthesized. The structures and properties of precursors and bi-CPc were characterized by 1H NMR, FT-IR, UV-Vis, elemental analysis and thermogravimetric analysis. Results showed that strong π-π* transition was demonstrated by UV-Vis absorption spectrum of bi-CPc. At the same time, it existed in a form of monomer in solution of N,N-dimethylformamide (DMF) and possessed excellent thermal stability. Redox behavior of bi-CPc was researched by cyclic voltammetry (CV), and energy level of LUMO and HOMO of bi-CPc matched with energy level of nano-TiO2 after calculating. Through further structural modification, it is expected to use as photosensitive dye with excellent performance for solar cells.

Key words: phthalocyanine, binuclear, coumarin, dye-sensitized solar cells