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化学进展 2013, Vol. 25 Issue (06): 999-1011 DOI: 10.7536/PC120949 前一篇   后一篇

• 综述与评论 •

可逆Diels-Alder反应

熊兴泉*, 江云兵   

  1. 华侨大学材料科学与工程学院 福建省高校功能材料重点实验室 厦门 361021
  • 收稿日期:2012-10-01 修回日期:2013-03-01 出版日期:2013-06-25 发布日期:2013-05-02
  • 通讯作者: 熊兴泉 E-mail:xxqluli@hqu.edu.cn
  • 基金资助:

    国家自然科学基金项目(No. 21004024);福建省自然科学基金项目(No. 2011J01046);福建省“高校新世纪优秀人才支持计划”(2012FJ-NCET-ZR03);福建省“高校杰出青年科研人才培育计划”(11FJPY02)和中央高校基本科研业务费“福建省杰出青年基金培育计划专项”基金资助

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Reversible Diels-Alder Reaction

Xiong Xingquan*, Jiang Yunbing   

  1. The Key Laboratory for Functional Materials of Fujian Higher Education, College of Materials Science & Engineering, Huaqiao University, Xiamen 361021, China
  • Received:2012-10-01 Revised:2013-03-01 Online:2013-06-25 Published:2013-05-02

通过高效的反应精确合成功能分子已成为现代化学发展的趋势之一。基于呋喃/马来酰亚胺 (MI) 之间的Diels-Alder(D-A)反应作为一种高效的和高选择性的点击反应, 克服了铜催化的叠氮/炔之间的1,3-偶极环化加成(CuAAC)反应中引起的金属污染等缺点, 为生物医药载体、功能性材料的制备提供更可行的途径。同时, 呋喃/MI 之间的D-A反应具备原料易得、反应条件温和及易发生retro D-A(rD-A)反应等优点, 在制备响应性材料领域备受关注。本文综述了近年基于呋喃/MI的可逆D-A反应在响应性聚合物合成、智能材料、生物分子及表面修饰等方面的应用, 并展望了D-A反应的发展前景。

关键词： 可逆D-A反应, 呋喃/MI, 智能材料, 生物大分子, 表面修饰

Synthesis of well-defined functional molecules through highly effective reactions has been one of development tendencies of modern chemistry. Diels-Alder (D-A) reaction between furan and maleimide (MI) derivatives as an important reaction of click chemistry provides a possible synthetic method for biomedicine carriers and functional materials, which overcomes the disadvantage of using toxic heavy metal in the copper catalyzed Huisgen type (3+2) dipolar cycloaddition reaction (CuAAC). In addition, the furan/MI D-A reaction has the following advantages, such as easily availability, mild reaction condition and thermal reversibility (retro Diels-Alder, rD-A), so it has been widely used to prepare environmentally responsive materials. In this paper, the applications of furan/MI D-A reaction in preparation of responsive polymers, smart materials, biomolecules and surface modification are emphasized. Furthermore, the prospects of D-A click reaction are also discussed. Contents
1 Introduction
2 Synthesis of topological polymers via D-A reaction
2.1 Synthesis of linear polymers via D-A reaction
2.2 Synthesis of star polymers via D-A reaction
3 Synthesis of self-repairing materials via D-A reaction
4 Synthesis of smart hydrogel via D-A reaction
5 Synthesis of smart materials via D-A reaction
6 Modification of biomacromolecules via D-A reaction
7 Surface modification via D-A reaction
8 Conclusions

Key words: reversible D-A reaction, furan/MI, smart materials, biomacromolecules, surface modification

中图分类号: 

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摘要

可逆Diels-Alder反应