Parent 1,4-dihydro-[1,2,3]triazolo[4,5-d][1,2,3]triazole and its derivatives as precursors for the design of promising high energy density materials

被引:0
|
作者
Kuznetsova, Agata N. [1 ,2 ]
Leonov, Nikita E. [1 ]
Anikin, Oleg V. [1 ]
Klenov, Michael S. [1 ]
Churakov, Aleksandr M. [1 ]
Strelenko, Yurii A. [1 ]
Novikov, Roman A. [1 ]
Fedyanin, Ivan V. [3 ]
Pivkina, Alla N. [4 ]
Kon'kova, Tatiana S. [4 ]
Sinditskii, Valery P. [5 ]
Smirnova, Anastasia D. [5 ]
Tartakovsky, Vladimir A. [1 ]
机构
[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, 47 Leninsky Prospect, Moscow 119991, Russia
[2] Lomonosov Moscow State Univ, Dept Chem, 1 Leninskie Gory, Moscow 119991, Russia
[3] Russian Acad Sci, AN Nesmeyanov Inst Organoelement Cpds, 28 Vavilova St, Moscow 119991, Russia
[4] Russian Acad Sci, NN Semenov Fed Res Ctr Chem Phys, 4 Kosygin St, Moscow 119991, Russia
[5] Mendeleev Univ Chem Technol, 9 Miusskaya Sq, Moscow 125047, Russia
基金
俄罗斯科学基金会;
关键词
FUSED HETEROCYCLE; 3,3'-AZOBIS(6-AMINO-1,2,4,5-TETRAZINE); PERFORMANCE; BEHAVIOR; 2-OXIDE; SALTS; NITRO;
D O I
10.1039/d4nj04427d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The design of novel high energy density materials (HEDMs) is still one of the significant challenges in the field of applied chemistry. Newly discovered scaffolds are rare, but they open up new possibilities for HEDM design. Herein, a simple and effective two-step approach to previously unknown 1,4-dihydro-[1,2,3]triazolo[4,5-d][1,2,3]triazole (1) is presented. This compound is an individual energetic material (d = 1.84 g cm-3, , Tonset = 193 degrees C (all experimental values), D = 8.5 km s-1, P = 34 GPa (calculated ones)), but may also serve as a scaffold for the synthesis of structurally diversified related compounds. The precursors of triazolo-triazole 1 are previously unknown 5-amino-4-diazo-4H-1,2,3-triazolium chloride (4) and 5-amino-4-diazo-4H-1,2,3-triazole (5), which can also serve as starting materials for the synthesis of a variety of novel heterocycles. For example, the diazo compound 5 was used for the regioselective synthesis of a 2,5-disubstituted triazolo-triazole 10 bearing an N4-tripoid fragment. Overall, the developed approach to triazolo-triazole 1, 5-amino-4-diazo-4H-1,2,3-triazolium chloride (4) and 5-amino-4-diazo-4H-1,2,3-triazole (5) is expected to make these high nitrogen systems more accessible and affordable for the design of nitrogen containing fused heterocycles.
引用
收藏
页码:311 / 320
页数:10
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