Acta Chimica Sinica ›› 2011, Vol. 69 ›› Issue (06): 673-679. Previous Articles     Next Articles

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  1. (浙江大学高分子科学与工程学系 高分子合成与功能构造教育部重点实验室
    硅材料国家重点实验室 杭州 310027)
  • 投稿日期:2010-10-27 修回日期:2010-11-25 发布日期:2010-11-25
  • 通讯作者: 施敏敏
  • 基金资助:


Synthesis and Energy Levels of Perylene Diimide Derivatives with the Substitutions of Secondary Amino Groups at Bay Positions

HU Xiao-Lian, SHI Min-Min, ZUO Li-Jian, FU Lei, DAI Shu-Lie, CHEN Hong-Zheng   

  1. (Department of Polymer Science and Engineering, Key Laboratory of Macromolecule Synthesis and Functionalization of Ministry of Education, State Key Lab of Silicon Materials, Zhejiang University, Hangzhou 310027)
  • Received:2010-10-27 Revised:2010-11-25 Published:2010-11-25
  • Contact: Min-Min SHI
  • Supported by:

    ;he Fundamental Research Funds for the Central Universities

A series of perylene diimide derivatives 2a2d with the substitutions of secondary amino groups at bay positions, were synthesized via simple Ullmann reaction, and their energy levels were characterized. From the UV-vis absorption spectra, it was found that, after the introduction of secondary amino into the bay position, the band gaps of perylene diimides became narrower, and the maximum absorption peaks were significantly red-shifted while compared to non-substituted parent compound. Thus, their absorption bands extended to the near-IR range. Through cyclic voltammetry, it was disclosed that 2a, 2c, and 2d exhibited both reversible reduction and oxidation processes, and their HOMO energy levels increased greatly, indicating bipolar semiconductive characteristics. Preliminary investigation of the application of bis-morpholine substituted perylene diimide 2d in organic photovoltaic devices was performed, and the results demonstrated that 2d could be used as both electron acceptor and electron donor.

Key words: bay position, secondary amino group, perylene diimide, energy level, photovoltaic property