2,2′-Azobis(1,5′-bitetrazole) with a N₁₀ Chain and 1,5′-Bitetrazolate-2N-oxides: Construction of Highly Energetic Nitrogen-Rich Materials Based on C–N-Linked Tetrazoles

Abstract

A series of high-nitrogen compounds, including a unique molecule 2,2′-azobis(1,5′-bitetrazole) with a branched N 10 chain and 1,5′-bitetrazolate-2N-oxides, were synthesized successfully based on C−N-linked 1,5′-bistetrazoles using azo coupling of N-amine bonds and N-oxide introduction strategies. All compounds were characterized by NMR spectroscopy, IR spectroscopy, elemental analysis, and differential scanning calorimetry, in which the structures of five compounds were further determined by single-crystal X-ray diffraction analysis (2, T-N10B, 3a, 3b, and THX). The nitrogen contents of these five compounds range from 63.62 (THX) to 83.43% (T-N10B), which are much higher than that of . The heat of formation for the prepared compounds was calculated by using the Gaussian 09 program, with T-N10B having the highest value of 5.13 kJ g −1 , about 6 times higher than that of CL-20 (0.83 kJ g −1 ). The calculated detonation performances by EXPLO5 v6.05.04 show that THX has excellent detonation performance (D = 9581 m s −1 , P = 35.93 GPa) and a remarkable specific impulse (I sp = 284.9 s).

Self-Assembly and Controllable Regulation of 1,5′-Bitetrazolate-2N-oxide-Based EMOFs toward High Dimensionality

“…Then, an aqueous solution of 1,5′-bistetrazole was oxidized with potassium peroxymonopersulfatem (Oxone) at 40 °C for 3 days. The pH of the reaction solution was adjusted to 4–5 by adding an appropriate amount of acid, and the oxidation product obtained was HBTNO ( 1 , yield: 56%).…”

“…In our recent study, we reported a 1,5′-bitetrazolate-2 N -oxide (HBTNO) with two tetrazole rings, which has an excellent nitrogen–oxygen content, high energy density, and good stability . Based on these promising characteristics, we further explored the synthesis of EMOFs using Cu­(II), Co­(II), Zn­(II), and Ag­(I) (EMOFs 2 – 5 ) in combination with BTNO – anions.…”

Enhancing Conjugation Effect to Develop Nitrogen-Rich Energetic Materials with Higher Energy and Stability

“…However, high-energy properties often frequently give rise to diminished stability. Tetrazole is the ideal candidate for balancing “energy and stability” among nitrogen-rich heterocyclic compounds because of its high nitrogen content, enthalpy of formation, and tendency toward lower sensitivity. , Polycyclic tetrazoles have gained significant attention in recent years due to their higher nitrogen content and energy potential. − …”

Synthesis of Bridged Tetrazoles with Promising Properties and Potential Applications by a One‐Step Finkelstein Reaction

“…Various synthetic strategies have been described for creating new energetic materials, such as the introduction of ring and cage strain, or aiming to reach the highest possible nitrogen content. [5][6][7][8] In order to achieve these properties in a compound, the same energetic building blocks are often used. [1][2] Well-known examples are functionalization with nitro, nitrato, nitrimino and nitramino groups, or the addition of covalent azides.…”