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Progress in Chemistry 2017, Vol. 29 Issue (5): 476-490 DOI: 10.7536/PC170209 Previous Articles   Next Articles

• Review •

Azo-Bridged Coupling Bisfurazan: Synthesis and Its Structure-Function Relationship Between Molecular Structure and Melting Point

Ruqin Liu1,2, Zhirong Suo2, Naizhen He2, Shuang Chen2, Ming Huang1*   

  1. 1. Institute of Chemical Materials, China Academy of Engineering Physics, Mianyang 621900, China;
    2. School of Materials Science and Engineering, Southwest University of Science and Technology, Mianyang 621010, China
  • Received: Revised: Online: Published:
  • Supported by:
    The work was supported by the Technology-Fundamental Research Project of State Administration of Science,Technology and Industry for National Defense of China (No.JSJL2015212A001).
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Azo-bridged coupling bisfurazan is formed by two same furazan rings via the azo-bridged coupling reaction. Azo-bridged coupling bisfurazan compounds are one of the nitrogen rich high-energy density materials with predominant thermal-chemical property, which have attracted great attention due to their excellent features such as high percentage of nitrogen, low carbon and hydrogen content, good oxygen balance, high formation enthalpy, and conjugated structure. And they have an optimistic and bright foreground for applying to the fields of high energetic explosive, as well as solid rocket propellant. The research advances of some azo-bridged coupling bisfurazan compounds, such as 3,3'-diamino-4,4'-azofurazan, 3,3'-dinitro-4,4'-azofurazan, azo-bridged coupling bisfurazan halide and azole substituted azo-bridged coupling bisfurazan, in recent 20 years were reviewed from a point view of synthetic methods in this paper. Effects of the side chain substituents on azo-bisfurazan melting point were discussed preliminarily based on the large amounts of melting point data from the literatures. Factors influencing azo-bisfurazan melting point mainly include hydrogen bonded effect, inductive effect, planarity effect, side chain substituent volume and symmetry effect. The structure-function relationship between azo-bisfurazan molecular structure and melting point was studied. This study could contribute to supporting a theoretical reference for the design and synthesis of the novel azo-bridged coupling furazan compounds with specified thermal-chemical performance.
1 Introduction
2 Synthesis of azo-bridged coupling bisfurazan
2.1 Diamino azofurazan and its derivatives
2.2 3,3'-Dinitro-4,4'-azofurazan (DNAzF)
2.3 Azofurazan halide
2.4 Cyano azofurazan and its derivatives
2.5 Azole substituted azofurazan
2.6 Other azo-bridged coupling bisfurazan
3 Structure-function relationship between molecular structure and melting point for azo-bridged coupling bisfurazan
3.1 The basic chemical structure and melting point data of azo-bridged coupling bisfurazan
3.2 Effect of simple substituent groups on melting point
3.3 Effect of the side chain heterocyclic substituents on melting point
3.4 Volume and planarity effect of the side chain substituents 3.5 Symmetry effect of the side chain substituents 4 Conclusion
Key words: high-energy density materials, azo-bridged coupling bisfurazan, synthesis, melting point, structure-function relationship

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