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化学进展 2017, Vol. 29 Issue (2/3): 216-230 DOI: 10.7536/PC160717 前一篇   后一篇

• 综述 •

水溶性苝酰亚胺类材料的合成及其生物应用

吴锦钧1, 杨震1, 焦剑梅2, 孙鹏飞1*, 范曲立1, 黄维1,2*   

  1. 1. 南京邮电大学 有机电子与信息显示国家重点实验室培育基地 信息材料与纳米技术研究院 江苏先进生物与化学制造协同创新中心 南京 210023;
    2. 南京工业大学 江苏省柔性电子重点实验室 先进材料研究院 江苏先进生物与化学制造协同创新中心 南京 211816
  • 收稿日期:2016-07-18 修回日期:2016-12-21 出版日期:2017-02-15 发布日期:2017-02-27
  • 通讯作者: 孙鹏飞, 黄维 E-mail:iampfsun@njupt.edu.cn;wei-huang@njtech.edu.cn
  • 基金资助:
    国家自然科学基金项目（No.61378081，21574064，51503103），江苏省自然科学基金青年基金项目（No.BK20150843），南京邮电大学引进人才科研启动基金项目（No.NY215017）和南京邮电大学科研基金项目（No.NY211003）资助
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The Synthesis and Biological Applications of Water-Soluble Perylene Diimides

Jinjun Wu1, Zhen Yang1, Jianmei Jiao2, Pengfei Sun1*, Quli Fan1, Wei Huang1,2*   

  1. 1. Key Lab for Organic Electronics and Information Displays & Institute of Advanced Materials, Jiangsu National Synergetic Innovation Center for Advanced Materials, Nanjing University of Posts and Telecommunications, Nanjing 210023, China;
    2. Key Lab of Flexible Electronics & Institute of Advanced Materials, Jiangsu National Synergetic Innovation Center for Advanced Materials, Nanjing Tech University, Nanjing 211816, China
  • Received:2016-07-18 Revised:2016-12-21 Online:2017-02-15 Published:2017-02-27
  • Supported by:
    The work was supported by the National Natural Science Foundation of China (No. 61378081, 21574064, 51503103), the Jiangsu Provincial Natural Science Foundation for Youth (No. BK20150843), and NUPTSF (No. NY215017, NY211003).
3，4，9，10-苝四甲酰二亚胺及其衍生物（PDIs）因其光、热、化学稳定性好，荧光量子效率高的优点，已经在有机场效应晶体管（OFET）、有机太阳能电池（OPV）、染料激光和有机电致发光器件（OLED）等方面使用，但其自身结构容易π-π堆积，导致水溶性差，限制了其在生物领域的进一步运用。因此，对PDIs进行修饰，获得可以用于生物体的水溶性PDIs显得尤为重要。本文综述了对PDIs进行水溶性修饰的各种方法：使用阴离子取代基、阳离子取代基和非离子取代基等在PDIs酰亚胺的氮原子位置或者湾位置进行修饰，利用取代基的水溶性、静电排斥作用或者空间位阻效应来实现PDIs的水溶性。同时，进一步阐述了水溶性PDIs在新型荧光探针、光声成像、化学治疗和光动态治疗等方面的应用。
关键词： 3,4,9,10-苝四甲酰二甲胺, 水溶性, 修饰, 生物应用
Perylene diimide and its derivatives (PDIs) have been widely used as organic field-effect transistor (OFET), organic photovoltaic cell (OPV), dye laser and organic light emitting diode (OLED) in the field of optoelectronic materials due to their photo, thermal, chemical stability and high fluorescence quantum yields. However, because of their inherent structure, PDIs have poor water-solubility and easily form aggregates, which has limited their applications in biological fields. So, it's essential to synthesize water-soluble PDIs. This paper systematically presents the synthetic methods for obtaining water-soluble PDIs by introducing anionic substituent, cationic substituent or non-ionic substituent into the imide-position or bay-region of PDIs. Some of these substituents are water-soluble, and the others will achieve the water-solubility of PDIs through electrostatic repulsion or steric hindrance. In addition, several novel biological applications have been listed, such as chemotherapy,photodynamic therapy and fluorescence imaging.PDIs can also be used as a promising photo-acoustic contrast agents due to their good light absorption and photostability.

Contents
1 Introduction
2 Modification of PDIs
3 Modification of water-soluble PDIs
3.1 Anionic substituent
3.2 Cationic substituent
3.3 Non-ionic substituent
4 Biological application of water-soluble PDIs
4.1 Fluorescence probe
4.2 Contrast agent of photo-acoustic imaging
4.3 Chemotherapy
4.4 Photo-sensitizer of photodynamic therapy
5 Conclusion

Key words: PDIs, water-soluble, modify, biological application

中图分类号: 

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