Synthesis, and single crystal structure of fully-substituted polynitrobenzene derivatives for high-energy materials

Yang, Wei; Lu, Huanchang; Liao, Longyu; Fan, Guijuan; Ma, Qing; Huang, Jingyun

doi:10.1039/c7ra13346d

Cited by 5 publications

(3 citation statements)

References 23 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The diazonium bond N4–N5 bond length of 1.095(2) Å is in the range of normal N≡N triple bond, which is almost equal to those of other previously reported diazonium inner salts (1.088(2) Å, 1.096(3) Å, 1.111(2) Å and 1.112(2) Å). Moreover, the diazonium group is coplanar with 1,2,4‐triazolate which can also attribute to one σ covalent bond and two π covalent bonds in the N≡N triple bond, comparing with non‐coplanar azido groups in 1,2,4‐triazole substituted polynitro‐benzene and 1,2,3‐triazole dendrictic esters . The packing diagram of 3 from Figure shows a “V” shape packing and no hydrogen bonding interaction obviously exists.…”

Section: Figurementioning

confidence: 98%

High Density Energetic Zwitterionic Diazonium 1,2,4‐Triazolate Resulting from an Interesting Bond Cleavage of E‐1,2‐Bis(3,4‐diamino‐1,2,4‐triazol‐5‐yl)‐ethane

Liao

et al. 2018

ChemistrySelect

Self Cite

View full text Add to dashboard Cite

An energetic zwitterion 5‐diazonium‐3‐trinitromethyl‐1,2,4‐triazolate (DTNMTz) was synthesized by an interesting bond cleavage of E‐1,2‐Bis(3,4‐diamino‐1,2,4‐triazol‐5‐yl)‐ethane. Its structure was confirmed by single‐crystal X‐ray diffraction. The physicochemical properties such as electrostatic potential, thermal properties and sensitivity towards impact, friction and electrostatic discharge were evaluated. Its heat of formation, detonation pressure and velocity were calculated. It is worth noting that this zwitterion behaves zero CO2 oxygen balance, and it has high density at ambient temperature (1.89 g cm−3), considerable detonation performance (D: 9317 m s−1, P: 37.6 GPa).

show abstract

Section: Figurementioning

confidence: 98%

High Density Energetic Zwitterionic Diazonium 1,2,4‐Triazolate Resulting from an Interesting Bond Cleavage of E‐1,2‐Bis(3,4‐diamino‐1,2,4‐triazol‐5‐yl)‐ethane

Liao

et al. 2018

ChemistrySelect

Self Cite

View full text Add to dashboard Cite

show abstract

“…The diazotization and conversion of triaminobenzenes have been reported [40]. Although 1,3,5-triaazidobenzenes are known and reported to be stable, most publications only deal with the theoretical calculations of these molecules [41][42][43][44][45][46][47][48], and there are only around 20 reported examples (including tetra/penta/hexa-azides) [40,43,44,[49][50][51][52][53][54][55].…”

Section: Diazotation and Azide Formationmentioning

confidence: 99%

Functionalized C3-Symmetric Building Blocks—The Chemistry of Triaminotrimesic Acid

et al. 2022

View full text Add to dashboard Cite

A series of C3-symmetric fully substituted benzenes were prepared based on alkyl triamino-benzene-tricarboxylates. Starting with a one step-synthesis, the alkyl triamino-benzene-tricarboxylates were synthesized using the corresponding cyanoacetates. The reactivity of these electronically sophisticated compounds was investigated by the formation of azides, the click reaction of the azides and a Sandmeyer-like reaction. Caused by the low stability of triaminobenzenes, direct N-alkylation was rarely reported. The use of the stable alkyl triamino-benzene-tricarboxylates allowed us total N-alkylation under standard alkylation conditions. The molecular structures of the C3-symmetric structures have been corroborated by an X-ray analysis.

show abstract

“…However, constrained by elemental composition, most of the polynitrophenyl compounds are unable to meet the future requirements due to their relatively low energy density. − In recent years, the combination of nitrogen heterocycles and polynitrophenyl skeleton has appeared as an effective means for the design of novel HREs (Scheme ). Owing to their activity toward nucleophiles, a number of nitrogen heterocycles such as imidazole, triazene, pyrazole, and triazole have been utilized to react with chloronitroarenes to yield highly thermostable EMs. − Although the inclusion of polynitrogen heterocycles into the conjugated system improves the heat of formation, it also results in reduced oxygen balance.…”

Section: Introductionmentioning

confidence: 99%

Highly Thermostable Insensitive Energetic Polynitrophenyl-Substituted Furazan (Furoxan)-Annelated Azepines

Liu¹,

Xiao

Duan³

et al. 2020

ACS Appl. Energy Mater.

View full text Add to dashboard Cite

Achieving high thermal stability and low mechanical sensitivity are two major goals in the development of energetic compounds. Six highly stable insensitive polynitrophenyl-substituted furazan (furoxan)-annelated azepines have been prepared and characterized in this work. All the involved compounds were characterized by 1H and 13C NMR spectroscopy, IR spectroscopy, and elemental analysis, and four of them were further supported by single-crystal X-ray diffraction investigations. Moreover, their thermal stabilities and mechanical sensitivities were evaluated. All energetic compounds exhibited excellent thermal stabilities with decomposition temperatures ranging from 290 to 333 °C. Compounds 1c and 2c exhibit extremely low mechanical sensitivity (IS >40 J and FS > 360 N). Based on experimental densities and calculated heat of formation, the detonation velocities and pressures for the energetic compounds were calculated using EXPLO5 (V6.04) with the corresponding results in the range of 26.4 to 29.9 GPa and 7979 m s–1 to 8356 m s–1. The detailed study based on Hirshfeld surfaces and electrostatic potential (ESP) analysis was used to illustrate the relationship between molecular structures and sensitivity of these compounds. The comprehensive performances of these materials are superior to those of the widely used heat-resistant explosive HNS (2,2′,4,4′,6,6′-hexanitrostilbene).

show abstract

Synthesis, and single crystal structure of fully-substituted polynitrobenzene derivatives for high-energy materials

Abstract: Novel energetic fully-substituted polynitrobenzene derivatives were synthesized from economical TCTNB and exhibit good thermal stabilities coupled with reasonable detonation performance.

Cited by 5 publications

References 23 publications

High Density Energetic Zwitterionic Diazonium 1,2,4‐Triazolate Resulting from an Interesting Bond Cleavage of E‐1,2‐Bis(3,4‐diamino‐1,2,4‐triazol‐5‐yl)‐ethane

High Density Energetic Zwitterionic Diazonium 1,2,4‐Triazolate Resulting from an Interesting Bond Cleavage of E‐1,2‐Bis(3,4‐diamino‐1,2,4‐triazol‐5‐yl)‐ethane

Functionalized C3-Symmetric Building Blocks—The Chemistry of Triaminotrimesic Acid

Highly Thermostable Insensitive Energetic Polynitrophenyl-Substituted Furazan (Furoxan)-Annelated Azepines

Contact Info

Product

Resources

About