High-Nitrogen Energetic Materials of 1,2,4,5-Tetrazine Family: Thermal and Combustion Behaviors

Sinditskii, Valery P.; Egorshev, V.Y.; Rudakov, Gennady F.; Филатов, С. Н.; Burzhava, Anna V.

doi:10.1007/978-3-319-27748-6_3

Cited by 10 publications

(5 citation statements)

References 53 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“… Derivatives of the title heterocycles with great application potential [ 3 , 4 , 7 , 12 , 13 , 17 ]. …”

Section: Schemes and Tablesmentioning

confidence: 99%

“…This unique ring contains four nitrogen atoms, which is the maximum content in a stable six-membered system. This specific structure has attracted scientists’ attention as an important candidate for high energy density materials (HEDMs, A, Scheme 1 ), as its thermal decomposition leads to ring opening and the release of a nitrogen molecule [ 1 , 2 , 3 ]. The high nitrogen content has also encouraged research into its biological activity (B, Scheme 1 ), which has resulted in compounds that have anti-tubercular, anti-cancer, or anti-malarial effects [ 4 , 5 , 6 ].…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis and Luminescent Properties of s-Tetrazine Derivatives Conjugated with the 4H-1,2,4-Triazole Ring

2022

View full text Add to dashboard Cite

New derivatives obtained by the combination of unique 1,2,4,5-tetrazine and 4H-1,2,4-triazole rings have great application potential in many fields. Therefore, two synthetic few-step methodologies, which make use of commercially available 4-cyanobenzoic acid (method A) and ethyl diazoacetate (method B), were applied to produce two groups of the aforementioned heterocyclic conjugates. In both cases, the target compounds were obtained in various combinations, by introducing electron-donating or electron-withdrawing substituents into the terminal rings, together with aromatic or aliphatic substituents on the triazole nitrogen atom. Synthesis of such designed systems made it possible to analyze the influence of individual elements of the structure on the reaction course, as well as the absorption and emission properties. The structure of all products was confirmed by conventional spectroscopic methods, and their luminescent properties were also determined.

show abstract

“… Derivatives of the title heterocycles with great application potential [ 3 , 4 , 7 , 12 , 13 , 17 ]. …”

Section: Schemes and Tablesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and Luminescent Properties of s-Tetrazine Derivatives Conjugated with the 4H-1,2,4-Triazole Ring

2022

View full text Add to dashboard Cite

show abstract

“…Note that the nonisothermal DSC trace of NTO collected at 5-10°C min À 1 shows only an exotherm that appears at 270-275°C. [50] Investigation of the thermal stability of tetrazine derivatives [51] has shown that the least stable group in the molecule is usually the substituent in the tetrazine cycle which decomposition controls decomposition of the whole molecule. Electron withdrawing properties of the tetrazine cycle, in its turn, tend to increase the thermal stability of the substituents.…”

Section: Thermal Stability Of Triazolotetrazinesmentioning

confidence: 99%

Synthesis and Physicochemical Properties of Energetic 1,2,4,5‐Tetrazinyl Derivatives of 5‐Nitro‐2,4‐dihydro‐1,2,4‐triazol‐3‐one

et al. 2021

Self Cite

View full text Add to dashboard Cite

By replacing the pyrazolyl fragment in 3,6-bis(3,5-dimethyl-1Hpyrazol-1-yl)-1,2,4,5-tetrazine with 3-nitro-1,2,4-triazol-5-one (NTO), both mono-and disubstitution products have been synthesized. Further interaction of the obtained compounds with O-and N-nucleophiles led to the preparation of a number of polynitrogen tetrazine derivatives, including 2-[6-amino-1,2,4,5-tetrazin-3-yl]-5-nitro-2,4-dihydro-3H-1,2,4-triazol-3-one and 5-nitro-2-[6-(1H-tetrazol-5-ylamino)-1,2,4,5-tetrazine-3-yl]-2,4-dihydro-3H-1,2,4-triazol-3-one. The reactions of nucleophilic substitution of symmetrically substituted tetrazine were shown to proceed more selectively. The resulting compounds were identified using 1 H, 13 CNMR spectroscopy, FTIR, LC-MS, and elemental analysis, as well as using X-ray diffraction analysis. The thermal stability of the new compounds was evaluated under isothermal and non-isothermal conditions and their energy characteristics were calculated. An unusual drop in stability was found on going from symmetrically substituted tetrazines to asymmetric ones.

show abstract

“…[3][4][5] Nitrogen-rich heterocyclic molecules particularly those of the tetrazine groups (sixmembered ring with four nitrogen atoms) are used in material sciences to make high density energy compounds, because their thermal decomposition leads to the ring opening, resulting in the formation of nitriles and nitrogen molecules. [6][7][8] Additionally, synthetic tetrazine derivatives have been used in molecular imaging. Examples included targeted labelling, delivery of radionuclide, and visualization of tumors in lung cells and mice; fluorescent label proteins on the surface and inside mammalian cells, [9][10][11][12] and covalent bonding of tetrazine molecules to the surface of cells to study cell-to-cell interactions 13 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and anticancer activity evaluation of some new 1,2,3,5-tetrazine derivatives attached to benzothiazole moiety

TSEMEUGNE¹,

Tsemeugne²,

Bah³

et al. 2022

Arkivoc

View full text Add to dashboard Cite

A series of novel tetrazine derivatives, containing benzothiazole framework, were prepared during the coupling reactions of some diazotized 2-aminobenzo[d]thiazole derivatives with p-acetaminophen. Their structures were elucidated based on NMR and MS spectrometry. The anticancer activity and the safety of the synthesized compounds along with the entire precursors were assessed against three human cancer cell lines and a normal cell line. All the synthesized compounds showed selective cytotoxic activity against the cancer cell lines used in comparison to the normal Vero cell line. Their IC50 values varied from 2.02 to 171.67 µM.

show abstract

High-Nitrogen Energetic Materials of 1,2,4,5-Tetrazine Family: Thermal and Combustion Behaviors

Cited by 10 publications

References 53 publications

Synthesis and Luminescent Properties of s-Tetrazine Derivatives Conjugated with the 4H-1,2,4-Triazole Ring

Synthesis and Luminescent Properties of s-Tetrazine Derivatives Conjugated with the 4H-1,2,4-Triazole Ring

Synthesis and Physicochemical Properties of Energetic 1,2,4,5‐Tetrazinyl Derivatives of 5‐Nitro‐2,4‐dihydro‐1,2,4‐triazol‐3‐one

Synthesis and anticancer activity evaluation of some new 1,2,3,5-tetrazine derivatives attached to benzothiazole moiety

Contact Info

Product

Resources

About