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化学进展 2018, Vol. 30 Issue (5): 658-672 DOI: 10.7536/PC171220 前一篇   后一篇

• 综述 •

含有七元碳环的有机共轭分子在光电材料中的应用

史丹丹1,2, 张西沙1, 张德清1,2*   

  1. 1. 中国科学院化学研究所 北京分子科学国家实验室 有机固体重点实验室 分子科学科教卓越中心 北京 100190;
    2. 中国科学院大学化学学院 北京 100049
  • 收稿日期:2017-12-12 修回日期:2018-01-16 出版日期:2018-05-15 发布日期:2018-04-25
  • 通讯作者: 张德清e-mail:dqzhang@iccas.ac.cn E-mail:dqzhang@iccas.ac.cn
  • 基金资助:
    中国科学院B类先导专项（No.XDB12010300）和国家自然科学基金项目（No.21602225，21661132006）资助
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Application of Organic Conjugated Frameworks Containing Seven-Membered Carbon Rings in Optoelectronic Materials

Dandan Shi1,2, Xisha Zhang1, Deqing Zhang1,2*   

  1. 1. Beijing National Laboratory for Molecular Sciences, Organic Solids Key Laboratory, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China;
    2. School of Chemistry, University of Chinese Academy of Sciences, Beijing 100049, China
  • Received:2017-12-12 Revised:2018-01-16 Online:2018-05-15 Published:2018-04-25
  • Supported by:
    The work was supported by the Strategic Priority Research Program of the CAS (No.XDB12010300) and the National Natural Science Foundation of China (No. 21602225, 21661132006).
苯环是构成有机光电材料的主要单元，非苯系的七元环共轭体系则在有机光电材料中应用较少，直到最近几年才开始受到关注。由于七元环的前线轨道与六元环的明显差异和七元环容易被氧化而形成稳定的芳香性环庚三烯正离子的特点，它的引入可能给有机材料带来特殊的性能和应用。本文首先从历史的角度回顾了七元共轭碳环的发现、合成与结构研究。然后，对七元碳环共轭分子的结构骨架进行了分类，并对这些结构骨架的合成方法进行了总结。对七元碳环共轭分子在近红外吸收、有机场效应晶体管、有机太阳能电池、刺激-响应等领域的应用进行了重点介绍，并对该领域的发展前景进行了展望。
关键词： 七元碳环, 有机共轭骨架, 光电材料, 合成, 性能
Benzene is one of the most widely used units in organic opto-electronic materials. Different from six-membered benzene, seven-membered carbon conjugated system has seen much less applications in opto-electronic materials. Until recently, some attention has been paid to this field. Because of its different molecular orbital characteristic from benzene and easiness to be oxidized, seven-membered carbon ring conjugated system may introduce special and interesting properties to organic opto-electronic materials. In this paper, the conjugated seven-membered carbon rings are reviewed from the point of discovery, synthesis and structural investigation. Then, the skeleton types containing seven-membered carbon rings are analyzed and the synthetic methods for these skeleton types are demonstrated. The applications of conjugated molecules containing seven-membered carbon rings in near infrared absorptive materials, organic field effect transistors, organic solar cells and stimuli-responsive systems are introduced. In the end, the future developments of this field are discussed.
Contents
1 Introduction
2 Conjugated frameworks containing 7-membered carbon ring
3 Representative synthetic methods for conjugated molecules containing 7-membered carbon ring
3.1 Cyclo-addition and electro-cyclization reactions
3.2 Friedel-Crafts reaction
3.3 Condensation reaction
3.4 Scholl-type oxidative coupling reaction
3.5 Metal mediated alkene or alkyne cyclization
3.6 Functionalization of 7-membered ring
4 Application of conjugated molecules containing 7-membered carbon ring in near infrared absorption systems
5 Application of conjugated molecules containing 7-membered carbon ring in organic field effect transistors
5.1 Azulene based systems
5.2 Non-azulene based systems
6 Application of conjugated molecules containing 7-membered carbon ring in organic solar cells
7 Application of conjugated molecules containing 7-membered carbon ring in stimuli-responsive systems
7.1 Azulene based systems
7.2 Non-azulene based systems
8 Conclusion and outlook
Key words: seven-membered carbon ring, organic conjugated frameworks, opto-electronic materials, synthesis, property

中图分类号: 

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