5940-53-4Relevant articles and documents
Synthesis, characterization, and energetic properties of diazido heteroaromatic high-nitrogen C-N compound
Huynh, My Hang V.,Hiskey, Michael A.,Chavez, David E.,Naud, Darren L.,Gilardi, Richard D.
, p. 12537 - 12543 (2005)
The synthesis, characterization, and energetic properties of diazido heteroaromatic high-nitrogen C-N compound, 3,6-diazido-1,2,4,5-tetrazine (DiAT), are reported. Its normalized heat of formation (NδHf), experimentally determined using an additive method, is shown to be the highest positive NδHf compared to all other organic molecules. The unexpected azido-tetrazolo tautomerizations and irreversible tetrazolo transformation of DiAT are remarkable compared to all other polyazido heteroaromatic high-nitrogen C-N compounds, for example, 2,4,6-triazido-1,3,5- triazine; 4,4′,6,6′-tetra(azido)hydrazo-1,3,5-triazine; 4,4′,6,6′-tetra(azido)azo-1,3,5-triazine; and 2,5,8-tri(azido)-1,3, 4,6,7,9,9b-heptaazaphenalene (heptazine).
3,6-Di(azido)-1,2,4,5-tetrazine: A precursor for the preparation of carbon nanospheres and nitrogen-rich carbon nitrides
Huynh, My Hang V.,Hiskey, Michael A.,Archuleta, Jose G.,Roemer, Edward L.,Gilardi, Richard
, p. 5658 - 5661 (2004)
A high-nitrogen compound, 3,6-di(azido)-1,2,4,5-tetrazine, was used as precursor for the preparation of carbon nanospheres (see SEM picture) and nitrogen-rich carbon nitrides. The conversions into both carbon-based materials are simple, occur under mild conditions (low temperature, no applied pressure), and require no vacuum systems, extraction, carbonization, and purification.
Synthesis of the bi-heterocyclic parent ring system 1,2,4-triazolo[4,3- b][1,2,4,5]tetrazine and some 3,6-disubstituted derivatives
Chavez, David E.,Hiskey, Michael A.
, p. 1329 - 1332 (1998)
The synthesis of the previously unknown parent ring system was developed. Treatment of 3-hydrazino-1,2,4,5-tetrazine (4) with diethoxymethyl acetate gave the parent ring system. Similar treatment of 3-(3,5- dimethylpyrazol-1-yl)-6-hydrazino-1,2,4,5-tetrazine (2) with one carbon cyclizing reagents gave 3,6-di-substituted derivatives of the 1,2,4-tetrazine ring system.
TETRAZINE AND AZOLES BASED IONIC MATERIALS FOR PROPELLANTS AND ITS MANUFACTURING METHOD THEREOF
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Paragraph 0041-0043, (2021/08/10)
The present invention relates to an azole-based ionic material for tetrazine-based propellant and a manufacturing method thereof. An azole-based ionic material for a tetrazine-based propellant comprising tetrazine-based azole-based cations in which 1 or 2 azole-based cations are connected to each other based on tetrazine is provided.
Improved Synthesis and Thermochemical Properties of Amino- and Hydrazino-1,2,4,5-Tetrazines
Kon’kova, Tat’yana S.,Matyushin, Yurii N.,Miroshnichenko, Evgeniy А.,Palysaeva, Nadezhda V.,Sheremetev, Aleksei B.
, p. 1449 - 1453 (2020/12/07)
[Figure not available: see fulltext.] Improved protocols for the synthesis of 3,6-diamino- and 3,6-dihydrazino-1,2,4,5-tetrazines as well as 6-amino[1,2,4]triazolo[4,3-b]-[1,2,4,5]tetrazine were developed. Combustion energies were determined by the bomb calorimetry and the enthalpies of formation in the standard state were calculated for the compounds of this study. Based on the obtained data, the contribution of the 1,2,4,5-tetrazine moiety to the enthalpy of combustion of its derivatives was estimated.
s-Tetrazines as a New Electrode-Active Material for Secondary Batteries
Min, Dong Joo,Miomandre, Fabien,Audebert, Pierre,Kwon, Ji Eon,Park, Soo Young
, p. 503 - 510 (2019/01/04)
Because of the limitations of conventional metal-oxide-based electrodes, studies on organic redox-active materials as alternative electrodes for secondary batteries are emerging. However, reported organic electrode materials are still limited to a few kinds of organic redox groups. Therefore, the development of new redox-active groups for high-performance electrode materials is indispensable. Here, we evaluate s-tetrazine derivatives as a new electrode material in Li-ion batteries and study their charge/discharge mechanisms by ex situ XPS measurements. The porous carbon CMK-3 was introduced to encapsulate the s-tetrazines, which allowed 100 % utilization of the theoretical capacity and stable cycle performance of the s-tetrazines by preventing dissolution of the molecules into the electrolytes. This new class of redox-active group can pave the way for the next-generation of energy storage systems.
An Unusual Layered Crystal Packing Gives Rise to a Superior Thermal Stability of Energetic Salt of 3,6-Bishydrazino-1,2,4,5-tetrazine
Zhang, Gu-Dan,Wang, Zhen,Zhang, Jian-Guo
, p. 512 - 517 (2018/05/30)
Five energetic salts of 3,6-bishydrazino-1,2,4,5-tetrazine (BHT), namely (BHT)2(NTO)3 (3), (BHT)(BTT)·2H2O (4), (BHT)(DNP)2 (5), (BHT)(NATr)2 (6), and (BHT)(FOX-7)2 (7), were synthesized and fully characterized by elemental analysis, FT-IR, and mass spectra. The crystal structures of salts 3 and 4 were obtained and determined. Sensitivities towards outside stimuli and thermal behaviors of all the compounds were investigated, besides, thermodynamics of both 3 and 4 were calculated as well. The compounds 3–7 exhibit splendid thermal stabilities and satisfactory sensitivities simultaneously. Notably, unlike the previously known layered packing, compound 4 was found to adopt an unusual layered crystal packing with arch layers alternately arranged upward or downward. It may play an important role in contributing to its superior thermal stability (350 °C), providing an enlightening thinking to design new highly thermal stable energetic materials.
Single-molecule magnet behaviour in a tetranuclear DyIII complex formed from a novel tetrazine-centered hydrazone Schiff base ligand
Lacelle,Brunet,Pialat,Holmberg,Lan,Gabidullin,Korobkov,Wernsdorfer,Murugesu
supporting information, p. 2471 - 2478 (2017/03/08)
Two analogous tetranuclear lanthanide complexes have been synthesized with the general formula [Ln4(vht)4(MeOH)8](NO3)4·aMeOH·bH2O, where H2vht = (3,6-bis(vanillidenehydrazinyl)-1,2,4,5-tetrazine) and Ln = DyIII (1), GdIII (2). These complexes are characterized by several techniques; including single-crystal X-ray diffraction, SQUID magnetometry and single-crystal micro-SQUID hysteresis loop measurements. Elucidation of the crystal structure of the complexes shows that the lanthanide ions are bridged by a tetrazine ring, a rare bridging moiety for lanthanide ions. Magnetic studies reveal that both 1 and 2 exhibit weak ferromagnetic exchange interactions between Ln ions, and 1 displaying Single-Molecule Magnet (SMM) behaviour with a magnetisation reversal barrier of Ueff = 158 K (τ0 = 1.06 × 10?7 s).
Synthesis of a tetrazine-based catecholamide derivative and its evaluation as a chelating agent for removal of Cd(II), Co(II), and Cu(II)
Lei, Shan,Jin, Bo,Peng, Rufang,Zhang, Qingchun,Chu, Shijin
, p. 2384 - 2392 (2017/08/02)
The synthesis and structural characterization of a tetrazine-based catecholamide (CAM) ligand, N,N′-bis(N″-(aminoethyl)-2,3-bis(hydroxy)benzamide)-1,2,4,5-tetrazine-3,6-diamine (5), were investigated. All compounds were characterized by 1H NMR spectroscopy, 13C NMR spectroscopy, and FTIR spectroscopy. The protonation equilibria of 5 and complexation capacities (log βpqr) of Cd2+, Co2 +, and Cu2+ complexes of 5 were evaluated through potentiometric titration and spectrophotometric titration, respectively. Species independent pM value (=?log [M]free) was used to compare metal affinities with the final sequence Cu2+?>?Cd2+?>?Co2+. Results show that 5 has potential for heavy metal removal.
A tetrazine templated method for the synthesis of ternary conjugates
Venkateswara Rao, Boddu,Dhokale, Snehal,Rajamohanan, Pattuparambil R.,Hotha, Srinivas
supporting information, p. 10808 - 10810 (2013/11/06)
Conjugation is an important reaction that enables coupling of molecules. Many protocols exist for the synthesis of binary conjugates from two different molecules or for the polyvalent display of a single molecule. There aren't many methods for the synthesis of ternary conjugates. However, methods for ternary conjugation are important for understanding the interplay of interactions between three biomolecules (or any three molecules per se). A strategy for ternary bioconjugation using inverse electron demand Diels-Alder reaction with tetrazine is studied. Ternary conjugation was demonstrated by the reaction of a model glyco-peptide binary conjugate with a fluorescent tagged olefin. The Royal Society of Chemistry 2013.
