From <i>N</i>‐Nitro to <i>N</i>‐Nitroamino: Preparation of High‐Performance Energetic Materials by Introducing Nitrogen‐Containing Ions

Yin, Ping; Shreeve, Jean’ne M.

doi:10.1002/ange.201507456

Cited by 26 publications

(6 citation statements)

References 34 publications

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“…High nitrogen energetic materials are an area of advanced high‐energy‐density materials (HEDMs) aimed at future defense and space sector needs [1]. At present time, bistriazole derivates have been intensively investigated as HEDMs, due to their high densities, high heats of formation, and high thermal stability [2–11]. The initial reactants of the bistriazole compounds reported in the above literature are Bis(5‐amino‐1H‐1,2,4‐triazol‐3‐yl) (BATZ) and Bis(5‐amino‐1H‐1,2,4‐triazol‐3‐yl)methane (BATZM) reported by Shreve and Charlesworth in 1956 [12], high nitrogen content and high thermal decomposition temperature (623 K and 566 K, respectively.)…”

Section: Introductionmentioning

confidence: 99%

“…are their most striking features. Based on them, the amino group even hydrogen on the triazole ring is replaced by other energetic groups (like nitro, nitroimino, trinitromethyl or dinitromethyl groups) through organic synthesis to obtain a series of energetic compounds and their salts with excellent performance [2–11]. Bis(3‐nitro‐1H‐1,2,4‐triazol‐5‐yl)methane (BNTZM) is a derivative of BATZM, the synthetic method is reported in [13].…”

Section: Introductionmentioning

confidence: 99%

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Crystal Structure, Thermal Behavior and Detonation Characterization of Bis(3‐nitro‐1H‐1,2,4‐triazol‐5‐yl)methane

Yan

Hong-ya

et al. 2020

Propellants Explo Pyrotec

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Bis(3‐nitro‐1H‐1,2,4‐triazol‐5‐yl)methane (BNTZM) was synthesized and the crystal structure was determined by X‐ray diffraction. It belongs to orthorhombic system with space group Fdd2. Its thermal behavior and non‐isothermal decomposition kinetics were studied with DSC and TG/DTG methods. The self‐accelerating decomposition temperature (TSADT), thermal ignition temperature (TTIT), and critical temperature of thermal explosion (Tb) are 540 K, 552 K, and 558 K, respectively. Its detonation velocity (D) and detonation pressure (P) were estimated using the nitrogen equivalent equation according to the experimental density. The above results of BNTZM were compared with those of Bis(5‐amino‐1H‐1,2,4‐triazol‐3‐yl)methane (BATZM) and 5,5'‐dinitroimino‐3,3’‐methylene‐1H‐1,2,4‐triazole (DNBTM), and the effect of amino, nitro and nitroimino group on them were discussed.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Crystal Structure, Thermal Behavior and Detonation Characterization of Bis(3‐nitro‐1H‐1,2,4‐triazol‐5‐yl)methane

Yan

Hong-ya

et al. 2020

Propellants Explo Pyrotec

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“…Conjugated energetic materials (CEMs) have emerged as promising candidates for photochemical direct optical initiation. Recently synthesized tetrazine- and tetrazole-based CEMs − have significant C–N and N–N content, giving them the advantage of high heats of formation and clean burning typically associated with high-nitrogen HEs while retaining the optical activity ubiquitous in conventional carbon-based conjugated materials. In fact, while most HEs are not photoactive and absorb only in the ultraviolet (UV) wavelength range, CEMs can have significant one-photon and TPA cross sections in the visible region that can be accessed by conventional lasers …”

Section: Introductionmentioning

confidence: 99%

Site-Specific Photodecomposition in Conjugated Energetic Materials

et al. 2018

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Nonadiabatic excited-state molecular dynamics (NEXMD) has been used to study photodecomposition in a class of recently synthesized bicyclic conjugated energetic materials (CEMs) composed of fused tetrazole and tetrazine derivatives with increasing oxygen substitutions. Modification by oxygen functionalization has already been demonstrated to increase the two-photon absorption intensity in the target CEMs while simultaneously improving oxygen balance. Photodecomposition mechanisms in materials that undergo nonlinear absorption could be used to achieve controlled, direct optical initiation. Here, we use NEXMD simulations to model the nonradiative relaxation and photodecomposition in CEMs following photoexcitation by a simulated Nd:YAG laser pulse. Excess electronic energy is quickly converted into vibrational energy on a sub-100 fs time scale resulting in bond dissociation. We find that, for the studied tetrazine derivatives, the bicyclic framework is an important structural feature that enhances the photochemical quantum yield and the high atomic oxygen content increases the relaxation lifetime and opens additional photodissociation pathways targeting the oxygen-substituted sites. The presented analysis scheme based on bond orders in the swarm of NEXMD trajectories is a useful tool for determining photochemical reactions.

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“…According to the literature [28], DABNT immediately decomposes without a melting-point. The DSC and TG curves of DABNT at different temperatures are shown in Figures 3 and 4.…”

Section: Non-isothermal Decomposition Propertiesmentioning

confidence: 97%

A Facile Synthesis of 3,3'-Dinitro-5,5'-Diamino-Bi-1,2,4-Triazole and Its Thermal Decomposition Study

Ma¹,

Lu²,

Qu³

et al. 2017

Cent. Eur. J. Energ. Mater.

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3,3'-Dinitro-5,5'-diamino-bi-1,2,4-triazole (DABNT) was synthesized by a facile method and its crystalline density was determined as 1.839 g·cm −3 at 293(2) K by X-ray diffraction. Its thermal decomposition kinetics and mechanism were studied by means of differential scanning calorimetry-thermogravimetry (DCS-TG), in situ thermolysis by rapid-scan Fourier transform infrared spectroscopy (RSFTIR) and simultaneous TG-IR technology. The results showed that the apparent activation energies obtained by the Kissinger, Ozawa and Starink methods were 122.9 kJ·mol , 118.4 kJ·mol −1 and 138.7 kJ·mol −1 , respectively. The decomposition reaction process of DABNT starts with the transformation from a primary amine to a secondary amine and then the loss of one nitro-group from the DABNT structure. Gaseous products, such as N2O and H2O, were detected from decomposition in the range of 50-300 °C. Density functional theory (DFT) calculations were further employed to illustrate the decomposition mechanism. The above-mentioned information on the synthesis and thermal behaviour is quite useful for the scale-up and evaluation of the thermal safety of DABNT.

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From N‐Nitro to N‐Nitroamino: Preparation of High‐Performance Energetic Materials by Introducing Nitrogen‐Containing Ions

Cited by 26 publications

References 34 publications

Crystal Structure, Thermal Behavior and Detonation Characterization of Bis(3‐nitro‐1H‐1,2,4‐triazol‐5‐yl)methane

Crystal Structure, Thermal Behavior and Detonation Characterization of Bis(3‐nitro‐1H‐1,2,4‐triazol‐5‐yl)methane

Site-Specific Photodecomposition in Conjugated Energetic Materials

A Facile Synthesis of 3,3'-Dinitro-5,5'-Diamino-Bi-1,2,4-Triazole and Its Thermal Decomposition Study

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