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Progress in Chemistry 2013, Vol. 25 Issue (06): 999-1011 DOI: 10.7536/PC120949 Previous Articles   Next Articles

• Review •

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: Revised: Online: Published:
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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

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Abstract

Reversible Diels-Alder Reaction