偶氮桥联二呋咱:合成及其分子结构-熔点的构效关系
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摘要
偶氮桥联二呋咱是由两个相同的单呋咱环经偶氮桥联反应所构成的。它是一类热化学性能卓越的富氮高能密度材料,因具有高含氮量、低碳氢、良好的氧平衡、高生成焓并具有共轭结构等优点而备受关注,在高能炸药和固体火箭推进剂等领域有着重要的应用前景。本文从合成角度综述了近二十年来一些典型的偶氮桥联二呋咱类化合物(如3,3'-二氨基-4,4'-偶氮呋咱、3,3'-二硝基-4,4'-偶氮呋咱、偶氮桥联二呋咱卤化物和唑基偶氮桥联二呋咱等)的研究进展,系统讨论了不同侧链取代基对偶氮桥联二呋咱熔点性质的影响,其影响因素主要包括:氢键效应、诱导效应、平面性效应、侧链取代基的体积大小以及对称性作用。通过梳理其分子结构-熔点的构效关系,可为选择性设计和合成具有特定热化学性能的新型偶氮桥联呋咱类化合物提供理论参考。
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,lowcarbon 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 viewof 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.
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,lowcarbon 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 viewof 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.
引文
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[23]Batog L V,Konstantinova L S,Kulikov A S,Makhova N N.Russ.Chem.Bull.Int.Ed.,2013,62:1388.
[24]Sheremetev A B,Aleksandrova N S,Yudin I L.Mendeleev Commun.,2003,13:31.
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[32]Tang Y X,Gao H X,Imler G H,Parrishc D A,Shreeve J M.RSC Adv.,2016,6:91477.
[33]Leonard P W,Chavez D E,Pagoria P F,Parrish D L.Propellants Explos.Pyrotech.,2011,36:233.
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[35]高莉(Gao L),杨红伟(Yang H W),伍波(Wu B),程广斌(Cheng G B),吕春绪(LüC X).含能材料(Chinese Journal of Energetic Materials),2013,21:226.
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[39]Luk’yanov O A,Pokhvisneva G V,Ternikova T V,Shlykova NI.Russ.Chem.Bull.Int.Ed.,2012,61:360.
[40]Petrosyan V A,Frolovsky V A.Russ.Chem.Bull.Int.Ed.,2000,49:1421.
[41]Sheremetev A B,Lyalin B V,Kozeev A M,Palysaeva N V,Struchkova M I,Suponitsky K Y.RSC Adv.,2015,5:37617.
[42]Tselinskii I V,Mel’nikova S F,Zelenov M P.Zh.Org.Khim.,1996,32:766.
[43]Romanova T V,Zelenov M P,Mel’nikova S F,Tselinsky I V.Russ.Chem.Bull.Int.Ed.,2009,58:2188.
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