Synthesis of linear and hyperbranched tetrazine-based polyhetarylene assemblies with high nitrogen content

Sagot, E.; Roux, A. Le; Soulivet, C.; Pasquinet, Éric; Poullain, Didier; Girard, Elzéar; Palmas, P.

doi:10.1016/j.tet.2007.07.097

Cited by 23 publications

(12 citation statements)

References 46 publications

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“…Sagot et al [275] have reported the efficient synthesis of poly(2,6-pyridinediyl-dihydro-stetrazinylene) (295) from pyridine-2,6-diamidrazone (294) under MW-activation. The reaction conditions were optimized, and the best result was obtained by the application of an irradiation power of 40 W at 150 °C for 20 min to give the polymer in a 47% yield (Scheme 68).…”

Section: Six-membered Heterocycles With Three or Four Nitrogen: Triazmentioning

confidence: 99%

Microwave-Assisted Synthesis of Bioactive Six-Membered Heterocycles and Their Fused Analogues

et al. 2016

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This review describes the formation of six-membered heterocyclic compounds and their fused analogues under microwave activation using modern organic transformations including cyclocondensation, cycloaddition, multicomponents and other modular reactions. The review is divided according to the main heterocycle types in order of increasing complexity, starting with heterocyclic systems containing one, two and three heteroatoms and their fused analogues. Recent microwave applications are reviewed, with special focus on the chemistry of bioactive compounds. Selected examples from the 2006 to 2015 literature are discussed.

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Section: Six-membered Heterocycles With Three or Four Nitrogen: Triazmentioning

confidence: 99%

Microwave-Assisted Synthesis of Bioactive Six-Membered Heterocycles and Their Fused Analogues

et al. 2016

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“…The macromolecules DHTZ-HM, DHTZ-TM and DHTZ-MB were synthesized by reacting DHTz with various bi-substituted isocyanates in polar aprotic solvents at 20 C for 48 h (Scheme 1).…”

Section: Selectivity In Cyclization Vs Polymerizationmentioning

confidence: 99%

“…[18][19][20] In fact, the synthesis of polymers based on triazole and triazine moieties could be traced back to 1950s. [21][22][23] The tetrazole and tetrazine could be even better moieties for constructing energetic polymers due to their higher nitrogen content.…”

mentioning

confidence: 99%

“…[21][22][23] The tetrazole and tetrazine could be even better moieties for constructing energetic polymers due to their higher nitrogen content. [24][25][26] It has been shown that the tetrazole-and tetrazine-based energetic polymers are usually more thermally stable and less sensitive. Therefore, such nitrogenrich polymers could be very promising candidates for energetic applications.…”

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confidence: 99%

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Novel nitrogen-rich energetic macromolecules based on 3,6-dihydrazinyl-1,2,4,5-tetrazine

et al. 2015

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Nitrogen-rich energetic macromolecules were synthesized by reacting dihydrazinyl-1,2,4,5-tetrazine (DHTz) with various diisocyanates. It has been shown that polymerization or cyclization reactions could take place depending on solvent systems and reaction conditions. The formed macrocycles and polymers were comprehensively characterized by IR, NMR, high resolution MS and SEM, while the thermal stability was studied by DSC. The energetic properties of our new compounds were investigated by bomb calorimetry, along with calculations using the EXPLO-5 code. It was found that macrocycle C-DHTZ-TM and corresponding polymer P-DHTZ-TM prepared on a basis of DHTZ and tetramethylene diisocyanate have larger heats of combustion than RDX, GAP and polyGLYN. C-DHTZ-TM has a comparable density and larger detonation velocity than TNT. The nitrogen content of C-DHTZ-TM and P-DHTZ-TM is larger than 47%. The thermal stability of DHTz-based energetic macromolecules was found to be higher than currently used energetic polymers including GAP, polyNIMMO and polyGLYN.The ADN based compositions bonded by 60% (by weight) of P-DHTZ-HM and P-DHTZ-MB polymers have higher theoretical specific impulse than that bonded by polyGLYN. Therefore, our new compounds could be promising ingredients as energetic binders or fillers. Moreover, all of the macrocycles have potential to be used as energetic gelators in gel propellants.

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“…Diamidrazone 23 was used as the monomer in a microwave-assisted polycondensation to give the poly(2,6-pyridinediyl-dihydro-stetrazinylene) 24 which was further oxidized to the desired tetrazine polymer 25 using sodium nitrite/aq. AcOH [ 26 ] (Figure 12). Following the same strategy, the previously unknown 1,3,5-triazine-2,4,6-triamidrazone 26 was subjected to polycondensation to yield the hyperbranched polymer 27.…”

Section: Synthesis Of Tetrazine-based Polymers Via Polycondensationmentioning

confidence: 99%

Nitrogen-Rich Polymers as Candidates for Energetic Applications

Pasquinet¹

2012

New Polymers for Special Applications

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Synthesis of linear and hyperbranched tetrazine-based polyhetarylene assemblies with high nitrogen content

Cited by 23 publications

References 46 publications

Microwave-Assisted Synthesis of Bioactive Six-Membered Heterocycles and Their Fused Analogues

Microwave-Assisted Synthesis of Bioactive Six-Membered Heterocycles and Their Fused Analogues

Novel nitrogen-rich energetic macromolecules based on 3,6-dihydrazinyl-1,2,4,5-tetrazine

Nitrogen-Rich Polymers as Candidates for Energetic Applications

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