Di(1<i>H</i>-tetrazol-5-yl)methane as Neutral Ligand in Energetic Transition Metal Complexes

Freis, Manuel; Klapötke, Thomas M.; Stierstorfer, Jörg; Szimhardt, Norbert

doi:10.1021/acs.inorgchem.7b00432

Cited by 47 publications

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References 33 publications

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“…In recent years, more and more research groups all over the world have been working intensively on new laser ignitable energetic materials . The laser initiation shows many advantages compared to conventional methods like mechanical stimuli or heat and investigated compounds do not require high sensitivities toward the customary stimuli.…”

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…The investigation of energetic coordinationc ompounds (ECC) is one of the most useful strategiesi nd iscovering new environmentally benign materials fori gnition and initiation mixtures. [1][2][3][4] Ignition implies the releasea nd transfer of energy in the form of heat, flame or subsonic shock waves. This is required for many differenta pplications such as ammunition or in gas generators (e.g.,a irbags, oxygen candles).…”

Section: Introductionmentioning

confidence: 99%

“…The use of late first row transition metals (Mn 2 + ,F e 2 + ,C o 2 + , Ni 2 + ,C u 2 + ,Z n 2 + )i sag ood compromise for: i) availability, ii)price, iii)density,i v) toxicity( only for Mn 2 + ,F e 2 + ,C u 2 + and Zn 2 + ), and v) the coordination ability to nitrogen-rich ligands because of low oxophilicity.U seful ECC contain:a )a metal cation, b) nitrogen-rich ligandsa nd c) coordinating or non-coordinating anions( either oxygen-rich such as NO 3 À ,C lO 4 À , N(NO 2 ) 2 À or nitrogen-rich such as N 3 À ,t etrazolates or triazolates). Various combinationsh ave been described in the literature.…”

Section: Introductionmentioning

confidence: 99%

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Methylsemicarbazide as a Ligand in Late 3d Transition Metal Complexes

Szimhardt

Stierstorfer

2018

Chemistry A European J

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Most ignition and initiation systems nowadays still contain poisonous chemicals such as lead styphnate and lead azide but also chromates and other compounds of high concern. Therefore, methylsemicarbazide (1, MSC), which can be prepared in a one-step reaction and in an extraordinary high yield of 95 %, has been evaluated as ligand in energetic coordination compounds. For the first time 25 new transition metal complexes (Mn , Ni , Co , Cu , and Zn ) using methylsemicarbazide (1) as the ligand were prepared and comprehensively analyzed by, for example, XRD, IR, EA, UV/Vis and DSC/DTA/TGA. Many show a strong energetic character, which can be tuned by using different anions such as Cl , SO , NO , ClO , picrate or styphnate. Selected compounds were additionally evaluated as lead-free primary explosives in initiation tests (nitropenta filled detonators) and in laser ignition systems. Especially compound 7 showed very promising results during these tests and could be a potential candidate for future applications.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Methylsemicarbazide as a Ligand in Late 3d Transition Metal Complexes

Szimhardt

Stierstorfer

2018

Chemistry A European J

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“…Loading more nitro groups and higher structural tension into a single molecule does improve explosive performance, but usually leads to complicated and not cost-effective synthetic procedures. By a trade-off of detonation performance and cost, HMX is regarded as the best military high-energetic explosives nowadays [7], although it is neither the most powerful one nor the cheapest one.Parallel to the intensive studies on molecule engineering on the backbone of nitrogen-rich organic energetic molecules [8,9], the exploration of advanced energetic materials extends to the crystal engineering on their energetic co-crystals [10-13], energetic salts [14][15][16][17][18][19][20], as well as coordination polymers or metal-organic frameworks [21][22][23][24][25][26][27]. The essential strategy is to control the intermolecular packing/linkage of the energetic organic fuel and oxidizer components in crystals by non-covalent interactions to modify/enhance the explosive performance and/or to reduce the sensitivity to a practicable level.…”

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Molecular perovskite high-energetic materials

et al. 2018

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Since the black powder, the first known explosive, was discovered by ancient Chinese in the seventh century, people have been finding powerful, stable, reliable and low-cost energetic materials for military equipment and civil industry. To obtain a better explosive performance, an efficient strategy is to load unstable chemical bonds [1][2][3], as well as to combine fuel with oxidizer components in a proper ratio for achieving sufficient combustion and rapid detonation [4][5][6]. An effective way is to incorporate fuel and oxidizer properties into a single molecule [7], as demonstrated by a series of classical organic nitro group/nitrogen-rich molecules, such as trinitrotoluene (TNT), pentaerythritol tetranitrate (PETN), cyclotrimethylene trinitramine (RDX), cyclotetramethylene tetranitramine (HMX), hexanitrohexaazaisowurtzitane (CL-20) and octanitrocubane (ONC) (Fig. S1). Loading more nitro groups and higher structural tension into a single molecule does improve explosive performance, but usually leads to complicated and not cost-effective synthetic procedures. By a trade-off of detonation performance and cost, HMX is regarded as the best military high-energetic explosives nowadays [7], although it is neither the most powerful one nor the cheapest one.Parallel to the intensive studies on molecule engineering on the backbone of nitrogen-rich organic energetic molecules [8,9], the exploration of advanced energetic materials extends to the crystal engineering on their energetic co-crystals [10-13], energetic salts [14][15][16][17][18][19][20], as well as coordination polymers or metal-organic frameworks [21][22][23][24][25][26][27]. The essential strategy is to control the intermolecular packing/linkage of the energetic organic fuel and oxidizer components in crystals by non-covalent interactions to modify/enhance the explosive performance and/or to reduce the sensitivity to a practicable level. However, for a specific energetic molecular component, it is highly challenging to predict/engineer the crystal structure of its co-crystals, salts, or metal-organic frameworks [10], and the examples with good detonation performance, high stability and low cost are still scarce.Here we present a promising solution, i.e., assembly of both low-cost organic fuel and oxidizer components into a closely packed, high-symmetry ternary compounds (vide infra), to achieve advanced energetic materials with a nice combination of high explosive power, high stability, and low cost. The presented materials belong to the so-called molecular perovskites [28] with a general formula of ABX 3 , which topologically mimic the cubic structure of the very well-known inorganic perovskites, the simplest high-symmetry structure for ternary compounds, but have at least one organic molecular component (usually A component). Recently, molecular perovskites have attracted growing attention, as illustrated by the extensive studies on methyl-ammonium lead iodide for high performance solar cells [29][30][31][32], and the phase transitions together with the ...

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Nitrogen‐rich Compounds with Multiple Azole Rings: Gas Generant, Enthalpy Enhancer and Applicable Cationic Component

2021

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Nitrogen‐rich polyazole derivatives were designed and synthesized from the commercially available 4,5‐dicyano‐2‐aminoimidazole. The relatively simple synthesis of multiple azole rings in desired compounds with good yields allows for an efficient scale‐up. All synthesized compounds were characterized by NMR and vibrational spectroscopy, elemental analysis, and DSC studies. The impact and friction sensitivities were measured by the BAM apparatus. The energy content of the target compounds was predicted by using density functional methods. Performing cautious characterization point out that these compounds offer a good combination of high nitrogen‐ and energy‐content with insensitivity towards friction and impact stimuli. These results indicate the superior potential of these nitrogen‐rich polyazole derivatives for enthalpy enhancement, gas generant, and cationic components in energetic salts.

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Di(1H-tetrazol-5-yl)methane as Neutral Ligand in Energetic Transition Metal Complexes

Cited by 47 publications

References 33 publications

Methylsemicarbazide as a Ligand in Late 3d Transition Metal Complexes

Methylsemicarbazide as a Ligand in Late 3d Transition Metal Complexes

Molecular perovskite high-energetic materials

Nitrogen‐rich Compounds with Multiple Azole Rings: Gas Generant, Enthalpy Enhancer and Applicable Cationic Component

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