Novel high performance energetic materials of fluorine-containing 2,6-dinitro-4-(trifluoromethyl)phenol derivatives with substituted azoles

Balachandar, K.; Thangamani, Arumugam

doi:10.1016/j.jfluchem.2021.109801

Cited by 3 publications

(3 citation statements)

References 32 publications

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“…It is unexpected that the thermal decomposition temperatures of DFTNAN is 55 °C lower than that of TNAN since fluorinated compounds usually show considerably higher thermal stability and lower sensitivities due to the C-F bond [ 16 , 17 ]. However, in Reichel’s work [ 18 ], fluorination leads to an energetically destabilizing effect of methyl nitrate and its fluorinated derivatives, which is caused by the shorter C-O and N-O bonds in molecular structures.…”

Section: Resultsmentioning

confidence: 99%

Probing the Reaction Mechanisms of 3,5-Difluoro-2,4,6-Trinitroanisole (DFTNAN) through a Comparative Study with Trinitroanisole (TNAN)

Jiao

et al. 2022

Materials

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To probe the thermal decomposition mechanisms of a novel fluorinated low-melting-point explosive 3,5-difluoro-2,4,6-trinitroanisole (DFTNAN), a comparative study with trinitroanisole (TNAN) was performed under different heating conditions. The thermal decomposition processes and initial reactions were monitored by DSC-TG-FTIR-MS and T-jump-PyGC-MS coupling analyses, respectively. The results show that fluorine decreased the thermal stability of the molecular structure, and the trigger bond was transferred from the ortho-nitro group of the ether to the para-nitro group. The possible reaction pathway of DFTNAN after the initial bond breakage is the rupture of the dissociative nitro group with massive heat release, which induces the ring opening of benzene. Major side reactions include the generation of polycyclic compounds and fluorine atom migration. Fluorine affects the thermal stability and changes the reaction pathway, and fluorinated products appear in the form of fluorocarbons due to the high stability of the C-F bond.

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Section: Resultsmentioning

confidence: 99%

Probing the Reaction Mechanisms of 3,5-Difluoro-2,4,6-Trinitroanisole (DFTNAN) through a Comparative Study with Trinitroanisole (TNAN)

Jiao

et al. 2022

Materials

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“…The trifluoromethyl moiety (CF 3 ) is a significant group in organic synthesis and drug chemistry, as well as in the realm of energetic materials [39,82–85] . The introduction of the trifluoromethyl group increases the density, enhances the thermal stability, and improves sensitivity owing to the excellent properties of the three fluorine atoms bonded to the carbon center [86–88] . The improvement of the detonation performance of trifluoromethyl group‐based materials is yet to be fully explored, unlike the F and NF 2 substituted trinitromethyl groups discussed earlier.…”

Section: Trifluoromethyl Group Based Energetic Materialsmentioning

confidence: 99%

“…[39,[82][83][84][85] The introduction of the trifluoromethyl group increases the density, enhances the thermal stability, and improves sensitivity owing to the excellent properties of the three fluorine atoms bonded to the carbon center. [86][87][88] The improvement of the detonation performance of trifluoromethyl group-based materials is yet to be fully explored, unlike the F and NF 2 substituted trinitromethyl groups discussed earlier. Therefore, a common strategy utilized to construct trifluoromethyl group-based energetic materials is to introduce both a trifluoromethyl moiety and detonation groups or rings.…”

Section: Trifluoromethyl Group Based Energetic Materialsmentioning

confidence: 99%

Fluorine‐Containing Functional Group‐Based Energetic Materials

Guo

Qin

Chen

et al. 2023

The Chemical Record

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Molecules featuring fluorine‐containing functional groups exhibit outstanding properties with high density, low sensitivity, excellent thermal stability, and good energetic performance due to the strong electron‐withdrawing ability and high density of fluorine. Hence, they play a pivotal role in the field of energetic materials. In light of current theoretical and experimental reports, this review systematically focuses on three types of energetic materials possessing fluorine‐containing functional groups F‐ and NF2‐ substituted trinitromethyl groups (C(NO2)2F, C(NO2)2NF2), trifluoromethyl group (CF3), and difluoroamino and pentafluorosulfone groups (NF2, SF5) and investigates the synthetic methods, physicochemical parameters, and energetic properties of each. The incorporation of fluorine‐containing functional moieties is critical for the development of novel high energy density materials, and is rapidly being adopted in the design of energetic materials.

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On-line Raman spectroscopy combined with multivariate curve resolution-alternating least squares (MCR-ALS) to investigate the synthesis mechanism of 3,5-diamino-1,2,4-triazole (DAT)

Han

Guo

et al. 2023

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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Novel high performance energetic materials of fluorine-containing 2,6-dinitro-4-(trifluoromethyl)phenol derivatives with substituted azoles

Cited by 3 publications

References 32 publications

Probing the Reaction Mechanisms of 3,5-Difluoro-2,4,6-Trinitroanisole (DFTNAN) through a Comparative Study with Trinitroanisole (TNAN)

Probing the Reaction Mechanisms of 3,5-Difluoro-2,4,6-Trinitroanisole (DFTNAN) through a Comparative Study with Trinitroanisole (TNAN)

Fluorine‐Containing Functional Group‐Based Energetic Materials

On-line Raman spectroscopy combined with multivariate curve resolution-alternating least squares (MCR-ALS) to investigate the synthesis mechanism of 3,5-diamino-1,2,4-triazole (DAT)

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