2020
DOI: 10.1002/slct.202002440
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Energetic Triazolo‐Triazolo‐Furazano‐Pyrazines: A Promising Fused Tetracycle Building Block with Diversified Functionalities and Properties

Abstract: In this study, high energy materials (HEMs) derived from 1,2,4‐triazolo[3,4‐d]‐1,2,4‐triazolo[3,4‐f]furazano[3,4‐b]pyrazine (TTFP) substituted with −NH2, −NHNO2, −ONO2, −NO2, and −N3 explosophoric groups were designed and computationally characterized. Density functional calculations with B3PW91/6‐31G(d,p) method were used to explore the optimized structures, energetic properties, and sensitivity of TTFP derivatives. It is found that the TTFP is an effective molecular backbone for improving the energy content … Show more

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Cited by 8 publications
(2 citation statements)
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“…Common sp 2 nitrogen-containing moieties in energetic compounds include five- and six-membered heterocycles with one or more nitrogen on the ring (including triazoles, tetrazoles, pyrazines, and triazines). Pyridine was selected as a test case for an sp 2 nitrogen-containing aromatic ring that would likely yield coformers due to the large number of pyridine-containing hydrates in the CSD (over a thousand) and its predicted strong interactions with hydrogen peroxide . Additionally, despite the large number of hydrates, there are only two examples of organic peroxosolvates with a pyridine-containing coformer (SEMXIU and UKEFEV), and in only one case, 2,3,5,6-tetrakis­(pyridin-2-yl)­pyrazine, do close contacts exist between the pyridine sp 2 nitrogen and H 2 O 2 (the four pyridyl groups accept hydrogen bonds from H 2 O 2 ).…”
Section: Introductionmentioning
confidence: 99%
“…Common sp 2 nitrogen-containing moieties in energetic compounds include five- and six-membered heterocycles with one or more nitrogen on the ring (including triazoles, tetrazoles, pyrazines, and triazines). Pyridine was selected as a test case for an sp 2 nitrogen-containing aromatic ring that would likely yield coformers due to the large number of pyridine-containing hydrates in the CSD (over a thousand) and its predicted strong interactions with hydrogen peroxide . Additionally, despite the large number of hydrates, there are only two examples of organic peroxosolvates with a pyridine-containing coformer (SEMXIU and UKEFEV), and in only one case, 2,3,5,6-tetrakis­(pyridin-2-yl)­pyrazine, do close contacts exist between the pyridine sp 2 nitrogen and H 2 O 2 (the four pyridyl groups accept hydrogen bonds from H 2 O 2 ).…”
Section: Introductionmentioning
confidence: 99%
“…Meanwhile, its characteristics of high nitrogen and low hydrocarbon content make it have the dual effect of not only increasing the material density, but also achieving better oxygen balance easily. [ 3,4 ] Among them, the nitrogen content of tetrazine compounds reached 68.3% is a very effective structural unit in the design of high‐energy insensitive energy‐containing materials, tetrazine compounds have high thermal stability, high positive heats of formation (HOF) and low sensitivity, because of their powerful N–N and C–N bonds. [ 5‐8 ] With the increase of oxygen atoms coordinated with tetrazine, the density and properties of the molecule are improved, and the whole molecule tends to be stable.…”
Section: Introductionmentioning
confidence: 99%