5,6-Fused bicyclic tetrazolo-pyridazine energetic materials

Sitong, Chen; Liu, Yuji; Feng, Yongan; Yang, Xianjin; Zhang, Qinghua

doi:10.1039/c9cc08782f

Cited by 83 publications

(60 citation statements)

References 27 publications

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“…Electrostatic potential (ESP) is a real and fundamentally significant physical property of compounds as it provides information about charge density distribution and molecular reactivity 5 , 32 . Hence, the surface electrostatic potential was taken into account in the analysis of electronic properties of the title compounds.…”

Section: Resultsmentioning

confidence: 99%

Screening for energetic compounds based on 1,3-dinitrohexahydropyrimidine skeleton and 5-various explosopheres: molecular design and computational study

Duan

Liu²,

Lu³

et al. 2020

Sci Rep

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In this paper, twelve 1,3-dinitrohexahydropyrimidine-based energetic compounds were designed by introducing various explosopheres into hexahydropyrimidine skeleton. Their geometric and electronic structures, heats of formation (HOFs), energetic performance, thermal stability and impact sensitivity were discussed. It is found that the incorporation of electron-withdrawing groups (–NO2, –NHNO2, –N3, –CH(NO2)2, –CF(NO2)2, –C(NO2)3) improves HOFs of the derivatives and all the substituents contribute to enhancing the densities and detonation properties (D, P) of the title compounds. Therein, the substitution of –C(NO2)3 features the best energetic performance with detonation velocity of 9.40 km s−1 and detonation pressure of 40.20 GPa. An analysis of the bond dissociation energies suggests that N–NO2 bond may be the initial site in the thermal decompositions for most of the derivatives. Besides, –ONO2 and –NF2 derivatives stand out with lower impact sensitivity. Characters with striking detonation properties (D = 8.62 km s−1, P = 35.08 GPa; D = 8.81 km s−1, P = 34.88 GPa), good thermal stability, and acceptable impact sensitivity (characteristic height H50 over 34 cm) lead novel compounds 5,5-difluoramine-1,3-dinitrohexahydropyrimidine (K) and 5-fluoro-1,3,5-trinitrohexahydropyrimidine (L) to be very promising energetic materials. This work provides the theoretical molecular design and a reasonable synthetic route of L for further experimental synthesis and testing.

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Section: Resultsmentioning

confidence: 99%

Screening for energetic compounds based on 1,3-dinitrohexahydropyrimidine skeleton and 5-various explosopheres: molecular design and computational study

Duan

Liu²,

Lu³

et al. 2020

Sci Rep

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“…Compared to monocyclic backbones, fused-ring backbones exhibit a higher number of modifiable chemical sites, which is conducive to the design of molecular structures. Numerous expected configurations can be constructed around these modifiable sites. − Tetrazolo[1,5- b ]pyridazine is one of the well-known fused-ring skeletons; based on this skeleton, several high-energy insensitive energetic compounds were prepared. , Most of these energetic compounds show high-energy insensitivity performance. The high performance and high nitrogen content make these compounds promising building blocks for self-assembly materials.…”

Section: Introductionmentioning

confidence: 99%

Self-Assembly of Nitrogen-Rich Heterocyclic Compounds with Oxidants for the Development of High-Energy Materials

Zheng

Chen

et al. 2021

ACS Appl. Mater. Interfaces

Self Cite

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The development of energetic materials with high energy and low sensitivity has attracted immense interests due to their widespread applications in aerospace technology and national defense. In this work, a promising self-assembly strategy was developed to prepare three high-energy materials (1–3) through the introduction of oxidant molecules into the crystal voids of the parent materials. The structures of these new materials were comprehensively examined by infrared spectroscopy, nuclear magnetic resonance (NMR) spectroscopy, and single-crystal X-ray diffraction. In these materials, three unique layer structures with hcb, sql, and interrupted sql topologies were observed, which were formed by the fused-ring-based energetic components. Windows with hexagonal, square, and rectangular structures were observed within these layer structures, which were occupied by H2O2, NO3 –, and ClO4 –, respectively. Oxidant molecules interacted with parent molecules via hydrogen bonds to form crystal structures of these materials. Moreover, the energetic property of these materials was estimated by computing methods. The calculation results revealed that these self-assembly materials exhibit excellent energetic properties. The highest energetic performance was observed for compound 3. The detonation velocity, detonation pressure, and specific impulse values were up to 9339 m·s–1, 42.5 GPa, and 308 s, respectively, which were greater than those of HMX. Furthermore, these materials exhibited good sensitivity, which was closely related to their unique crystal structures. The high performance of these materials indicated that the self-assembly strategy should be a promising method for the development of novel energetic materials.

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“…[21][22][23][24][25][26] In this latter category, heterocyclization reactions have been crucial to the realization of structures with improved kinetic stability and physical properties. [1][2][3][4][5][6][7][8][9][10][11][12][21][22][23][24][25][26] Among the most important cycloadditions is the so-called Huisgen [2+3] cycloaddition, which results in the joining of reactive and (frequently) impact sensitive azides with reactive alkynes into kinetically stable five-membered 1,2,3-triazole rings. [27][28][29] Azole based systems are of interest as novel high explosives due to the remarkable stability of the five-membered heteroaromatic ring, which makes this class of molecules generally more insensitive than energetic materials with comparable nitrogen content.…”

Section: Introductionmentioning

confidence: 99%

“…Novel cycloaddition reactions are of fundamental interest to synthetic chemistry, as (hetero)cyclic compounds play important roles in tuning stability, [1][2][3][4][5][6][7][8][9][10][11][12] electronic properties, [13][14][15] and biological activity of molecules. [16][17][18][19][20] Access to specic or novel approaches for cyclization are of fundamental interest for enhancing the synthetic chemist's toolbox.…”

Section: Introductionmentioning

confidence: 99%

Transition-metal-mediated reduction and reversible double-cyclization of cyanuric triazide to an asymmetric bitetrazolate involving cleavage of the six-membered aromatic ring

et al. 2021

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5,6-Fused bicyclic tetrazolo-pyridazine energetic materials

Abstract: Two 5,6-fused tetrazolo-pyridazine compounds were synthesized and characterized, which exhibited high thermal stability, excellent energetic properties and low mechanical sensitivity.

Cited by 83 publications

References 27 publications

Screening for energetic compounds based on 1,3-dinitrohexahydropyrimidine skeleton and 5-various explosopheres: molecular design and computational study

Screening for energetic compounds based on 1,3-dinitrohexahydropyrimidine skeleton and 5-various explosopheres: molecular design and computational study

Self-Assembly of Nitrogen-Rich Heterocyclic Compounds with Oxidants for the Development of High-Energy Materials

Transition-metal-mediated reduction and reversible double-cyclization of cyanuric triazide to an asymmetric bitetrazolate involving cleavage of the six-membered aromatic ring

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