Synthesis, Characterization, and Energetic Properties of Diazido Heteroaromatic High-Nitrogen C−N Compound

Huynh, My Hang V.; Hiskey, Michael A.; Chávez, David E.; Naud, Darren L.; Gilardi, Richard

doi:10.1021/ja0509735

Cited by 298 publications

(189 citation statements)

References 39 publications

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“…In DSC, physical parameters like mass, heat flow, heat capacity and enthalpy [20] are measured with respect to time and temperature. This technique is useful for thermal studies of nitrogen rich energetic molecules.…”

Section: Differential Scanning Calorimetry (Dsc)mentioning

confidence: 99%

Design and Evaluation of the Thermal Properties of Di-, Tri- and Tetra-Azido-Esters

Kumar¹,

Kumar²,

Yamajala³

et al. 2017

Cent. Eur. J. Energ. Mater.

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A group of polycyclic and aliphatic azido-esters (as energetic plasticizers) have been synthesized by simple synthetic routes and their molecular structures were confirmed by spectroscopic techniques. In addition, their thermal and rheological properties have been determined utilizing DSC, TGA, viscosity, and contact angle. Computational studies of these plasticizers have been performed by means of DFT (B3LYP/6-31G*) to estimate possible stable structures, energies, heat of formation, bond dissociation energies, IR and NMR spectra etc. Their compatibility with glycidyl azide polymer (GAP) binder was studied to explore their applicability in propellants. All of these molecules are novel and have been synthesized with the possibility of scale up.

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Section: Differential Scanning Calorimetry (Dsc)mentioning

confidence: 99%

Design and Evaluation of the Thermal Properties of Di-, Tri- and Tetra-Azido-Esters

Kumar¹,

Kumar²,

Yamajala³

et al. 2017

Cent. Eur. J. Energ. Mater.

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“…Therefore, five-or six-membered nitrogen-containing heterocycles have been traditional sources of energetic materials. Triazole, tetrazole, and tetrazine derivatives have been investigated extensively as high-energy density materials (HEDMs) both theoretically and experimentally [19][20][21][22][23][24].…”

Section: Introductionmentioning

confidence: 99%

Decomposition Mechanisms of Nitrogen Rich Pyrotechnics, DHT, DIAT and DAAT

Gümüş¹,

Uygur²,

Gümüş³

2017

MOCR

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Abstract. The decomposition mechanism of nitrogen rich, environmentally friendly (green) pyrotechnics DHT (3,6-di(hydrazino)-1,2,4,5-tetrazine), DIAT (3,6-diazido-1,2,4,5-tetrazine) and DAAT (3,3-Azobis (6-amino-1,2,4,5-tetrazine) were investigated theoretically at the level of MP2/6-31G(d,p) level. The reaction coordinates for the decomposition were drawn and energy profile was built for all three. The decomposition products of these pyrotechnics are mainly nitrogen gas together with small carbon containing fragments. The reactants, intermediates, products were computed to be minima at the potential energy surface, on the other hand, the transition states were located on saddle points on the corresponding reactions.

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“…[19] Recently, these derivatives have also found numerous new applications ranging from optical waveguides [20] and data storage devices [21] to lightswitchable receptors [22] , and it is likely that new applications and discoveries will be made as the chemistries and structures are further refined. [23] In contrast, very few examples of the synthesis or utilization of (N-phenyl-N'- [1,3,5]triazinyl)diazenes [24,25] , and even less of bis- [1,3,5]triazinyl diazenes [26,27] , can be found in the literature. The main reason is probably the difficulty of synthesizing such compounds by using the traditional diazotization-coupling route, which is employed in the synthesis of various azobenzene compounds.…”

Section: Introductionmentioning

confidence: 99%

Preparation and characterization of bis‐[1,3,5]triazinyl diazenes and their utilization as flame retardants in polypropylene films

Tirri

Aubert

Pawelec

et al. 2014

J of Applied Polymer Sci

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A series of bis- [1,3,5]triazinyl diazenes and two metal complexes thereof were synthesized and tested as new flame retardants in polypropylene films. It was observed that electron withdrawing triazinyl ring substituents (i.e. Cl and phenyl moieties) improved the thermal stability of diazene compounds, whereas electron donating groups (i.e. methoxy, dimethylamino and ethylthio moieties) had a destabilizing effect. TGA, DTA/DSC, NMR and ATR-FTIR were used for the characterization. Quantum mechanical modeling (Gaussian 09) was also utilized to facilitate the interpretation of the NMR data. Bis-(4,6-dichloro-[1,3,5]triazin-2-yl)-diazene 1 and bis-(4,6-dimethoxy-[1,3,5]triazin-2-yl)-diazene 2 were found to be effective flame retardants in polypropylene films and DIN4102-1 B2 classification was reached already at a loading of 0.5 wt%. Interestingly, the copper complex of 2 showed even higher fire retardant activity than its precursor 2, whereas the corresponding zinc complex exhibited lower flame retardant efficacy than its precursor.

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Synthesis, Characterization, and Energetic Properties of Diazido Heteroaromatic High-Nitrogen C−N Compound

Cited by 298 publications

References 39 publications

Design and Evaluation of the Thermal Properties of Di-, Tri- and Tetra-Azido-Esters

Design and Evaluation of the Thermal Properties of Di-, Tri- and Tetra-Azido-Esters

Decomposition Mechanisms of Nitrogen Rich Pyrotechnics, DHT, DIAT and DAAT

Preparation and characterization of bis‐[1,3,5]triazinyl diazenes and their utilization as flame retardants in polypropylene films

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