高等学校化学学报

高等学校化学学报 ›› 2004, Vol. 25 ›› Issue (3): 454.

• 研究论文 • 上一篇    下一篇

新型有机电子受体氟代苝酰亚胺的合成与表征

施敏敏, 陈红征, 孙景志, 叶坚, 汪茫   

  1. 浙江大学高分子科学与工程学系, 硅材料国家重点实验室, 杭州 310027
  • 收稿日期:2003-01-09 出版日期:2004-03-24 发布日期:2004-03-24
  • 通讯作者: 汪　茫(1938出生),男,教授,博士生导师,主要从事有机半导体材料研究.E-mail;mwang@zju.edu.cn E-mail:mwang@zju.edu.cn
  • 基金资助:

    国家自然科学基金(批准号;50173021;50225312);教育部跨世纪人才基金(2001年)资助

Synthesis and Characterization of a Novel Electron Acceptor——Fluoroperylene Diimide

SHI Min-Min, CHEN Hong-Zheng, SUN Jing-Zhi, YE Jian, WANG Mang   

  1. State Key Lab of Silicon Materials, Department of Polymer Science and Engineering, Zhejiang University, Hangzhou 310027, China
  • Received:2003-01-09 Online:2004-03-24 Published:2004-03-24

PDF (PC)

被引次数

21

摘要： 设计和合成了一种新型有机电子受体N,N′-二(五氟代苯基)-3,4,9,10-苝四羧基二酰亚胺(DFPP),利用傅里叶红外光谱和核磁共振谱等方法表征了DFPP的分子结构,用紫外-可见吸收光谱、循环伏安法和电子自旋共振谱等手段证明了DFPP中极低的最低未占有轨道(LUMO)能级为-4.37eV.另外,还发现了DFPP薄膜的独特聚集态结构,五氟代苯基正好处于相邻分子苝环的正上方或正下方.

关键词: 电子受体, 氟代苝酰亚胺, 最低未占有轨道, 聚集态结构

Abstract: A novel electron acceptor, N,N′ diperfluorophenyl 3,4,9,10 perylenetetracarboxylic diimide (DFPP) with a good solubility and a high electron affinity was designed and prepared. Its molecular structure was characterized by FTIR and NMR measurements. As demonstrated by UV Vis, CV and ESR, the DFPP possessed much lower lowest unoccupied molecular orbital(LUMO) energy level of -4 37 eV, and the radical anion of DFPP could exist stoadily in the solution of DFPP in DMF because multiple strong electron withdrawing F atoms were introduced in the molecular structure of DFPP. Furthermore, through the simulation of the molecular conformation and the theoretical examinations of molecular interactions, the unique aggregate structure of DFPP was found; due to the disruption of the planarity of molecule structure and the increasing of intermolecular repulsion caused by the fluorination, and the radical anion of DFPP coule exist steadily in the solution of DFPP molecules stacked with the perfluorinated phenyl groups straightly above or below the perylene cores of the adjacent DFPP molecules.

Key words: Electron acceptor, Fluoroperylene diimide, LUMO, Aggregate structure

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