3,6,7-Triamino-[1,2,4]triazolo[4,3-b][1,2,4]triazole: A Non-toxic, High-Performance Energetic Building Block with Excellent Stability

A novel strategy for the design of energetic materials that uses fused amino‐substituted triazoles as energetic building blocks is presented. The 3,6,7‐triamino‐7H‐[1,2,4]triazolo[4,3‐b][1,2,4]triazolium (TATOT) motif can be incorporated into many ionic, nitrogen‐rich materials to form salts with ad...

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Published in	Chemistry : a European journal Vol. 21; no. 25; pp. 9219 - 9228
Main Authors	Klapötke, Thomas M., Schmid, Philipp C., Schnell, Simon, Stierstorfer, Jörg
Format	Journal Article
Language	English
Published	Weinheim WILEY-VCH Verlag 15.06.2015 WILEY‐VCH Verlag Wiley Subscription Services, Inc
Subjects	Alternative energy sources Cations Chemistry crystal structures energetic materials Friction Mathematical analysis Nitrates nitrogen Physicochemical properties Stability Stimuli Toxicity triazoles triazoles cations energetic materials crystal structures nitrogen
Online Access	Get full text
ISSN	0947-6539 1521-3765
DOI	10.1002/chem.201500982

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Abstract	A novel strategy for the design of energetic materials that uses fused amino‐substituted triazoles as energetic building blocks is presented. The 3,6,7‐triamino‐7H‐[1,2,4]triazolo[4,3‐b][1,2,4]triazolium (TATOT) motif can be incorporated into many ionic, nitrogen‐rich materials to form salts with advantages such as remarkably high stability towards physical or mechanical stimuli, excellent calculated detonation velocity, and toxicity low enough to qualify them as “green explosives”. Neutral TATOT can be synthesized in a convenient and inexpensive two‐step protocol in high yield. To demonstrate the superior properties of TATOT, 13 ionic derivatives were synthesized and their chemical‐ and physicochemical properties (e.g., sensitivities towards impact, friction and electrostatic discharge) were investigated extensively. Low toxicity was demonstrated for neutral TATOT and its nitrate salt. Both are insensitive towards impact and friction and the nitrate salt combines outstanding thermal stability (decomposition temperature=280 °C) with promising calculated energetic values. Triaminotriazolotriazolium (TATOT) nitrate (see figure) can be synthesized safely by a two‐step protocol. TATOT shows no aquatic toxicity, excellent stability towards thermal and physical stimuli, as well as good energetic performance. The TATOT cation is a “green”, inexpensive energetic building block and a promising alternative to currently used nitrogen‐rich cations, such as hydrazinium, hydroxylammonium, or guanidinium cations.
AbstractList	A novel strategy for the design of energetic materials that uses fused amino‐substituted triazoles as energetic building blocks is presented. The 3,6,7‐triamino‐7H‐[1,2,4]triazolo[4,3‐b][1,2,4]triazolium (TATOT) motif can be incorporated into many ionic, nitrogen‐rich materials to form salts with advantages such as remarkably high stability towards physical or mechanical stimuli, excellent calculated detonation velocity, and toxicity low enough to qualify them as “green explosives”. Neutral TATOT can be synthesized in a convenient and inexpensive two‐step protocol in high yield. To demonstrate the superior properties of TATOT, 13 ionic derivatives were synthesized and their chemical‐ and physicochemical properties (e.g., sensitivities towards impact, friction and electrostatic discharge) were investigated extensively. Low toxicity was demonstrated for neutral TATOT and its nitrate salt. Both are insensitive towards impact and friction and the nitrate salt combines outstanding thermal stability (decomposition temperature=280 °C) with promising calculated energetic values. Triaminotriazolotriazolium (TATOT) nitrate (see figure) can be synthesized safely by a two‐step protocol. TATOT shows no aquatic toxicity, excellent stability towards thermal and physical stimuli, as well as good energetic performance. The TATOT cation is a “green”, inexpensive energetic building block and a promising alternative to currently used nitrogen‐rich cations, such as hydrazinium, hydroxylammonium, or guanidinium cations. A novel strategy for the design of energetic materials that uses fused amino-substituted triazoles as energetic building blocks is presented. The 3,6,7-triamino-7H-[1,2,4]triazolo[4,3-b][1,2,4]triazolium (TATOT) motif can be incorporated into many ionic, nitrogen-rich materials to form salts with advantages such as remarkably high stability towards physical or mechanical stimuli, excellent calculated detonation velocity, and toxicity low enough to qualify them as "green explosives". Neutral TATOT can be synthesized in a convenient and inexpensive two-step protocol in high yield. To demonstrate the superior properties of TATOT, 13 ionic derivatives were synthesized and their chemical- and physicochemical properties (e.g., sensitivities towards impact, friction and electrostatic discharge) were investigated extensively. Low toxicity was demonstrated for neutral TATOT and its nitrate salt. Both are insensitive towards impact and friction and the nitrate salt combines outstanding thermal stability (decomposition temperature=280°C) with promising calculated energetic values. A novel strategy for the design of energetic materials that uses fused amino-substituted triazoles as energetic building blocks is presented. The 3,6,7-triamino-7H-[1,2,4]triazolo[4,3-b][1,2,4]triazolium (TATOT) motif can be incorporated into many ionic, nitrogen-rich materials to form salts with advantages such as remarkably high stability towards physical or mechanical stimuli, excellent calculated detonation velocity, and toxicity low enough to qualify them as "green explosives". Neutral TATOT can be synthesized in a convenient and inexpensive two-step protocol in high yield. To demonstrate the superior properties of TATOT, 13 ionic derivatives were synthesized and their chemical- and physicochemical properties (e.g., sensitivities towards impact, friction and electrostatic discharge) were investigated extensively. Low toxicity was demonstrated for neutral TATOT and its nitrate salt. Both are insensitive towards impact and friction and the nitrate salt combines outstanding thermal stability (decomposition temperature=280 °C) with promising calculated energetic values. A novel strategy for the design of energetic materials that uses fused amino‐substituted triazoles as energetic building blocks is presented. The 3,6,7‐triamino‐7 H ‐[1,2,4]triazolo[4,3‐b][1,2,4]triazolium (TATOT) motif can be incorporated into many ionic, nitrogen‐rich materials to form salts with advantages such as remarkably high stability towards physical or mechanical stimuli, excellent calculated detonation velocity, and toxicity low enough to qualify them as “green explosives”. Neutral TATOT can be synthesized in a convenient and inexpensive two‐step protocol in high yield. To demonstrate the superior properties of TATOT, 13 ionic derivatives were synthesized and their chemical‐ and physicochemical properties (e.g., sensitivities towards impact, friction and electrostatic discharge) were investigated extensively. Low toxicity was demonstrated for neutral TATOT and its nitrate salt. Both are insensitive towards impact and friction and the nitrate salt combines outstanding thermal stability (decomposition temperature=280 °C) with promising calculated energetic values. A novel strategy for the design of energetic materials that uses fused amino-substituted triazoles as energetic building blocks is presented. The 3,6,7-triamino-7H-[1,2,4]triazolo[4,3-b][1,2,4]tri azolium (TATOT) motif can be incorporated into many ionic, nitrogen-rich materials to form salts with advantages such as remarkably high stability towards physical or mechanical stimuli, excellent calculated detonation velocity, and toxicity low enough to qualify them as "green explosives". Neutral TATOT can be synthesized in a convenient and inexpensive two-step protocol in high yield. To demonstrate the superior properties of TATOT, 13 ionic derivatives were synthesized and their chemical- and physicochemical properties (e.g., sensitivities towards impact, friction and electrostatic discharge) were investigated extensively. Low toxicity was demonstrated for neutral TATOT and its nitrate salt. Both are insensitive towards impact and friction and the nitrate salt combines outstanding thermal stability (decomposition temperature=280 degree C) with promising calculated energetic values. Triaminotriazolotriazolium (TATOT) nitrate (see figure) can be synthesized safely by a two-step protocol. TATOT shows no aquatic toxicity, excellent stability towards thermal and physical stimuli, as well as good energetic performance. The TATOT cation is a "green", inexpensive energetic building block and a promising alternative to currently used nitrogen-rich cations, such as hydrazinium, hydroxylammonium, or guanidinium cations.
Author	Schnell, Simon Klapötke, Thomas M. Stierstorfer, Jörg Schmid, Philipp C.
Author_xml	– sequence: 1 givenname: Thomas M. surname: Klapötke fullname: Klapötke, Thomas M. email: tmk@cup.uni-muenchen.de organization: Department of Chemistry, Energetic Materials Research, Ludwig Maximilian University, Butenandtstr. 5-13 (D), 81377 München (Germany) – sequence: 2 givenname: Philipp C. surname: Schmid fullname: Schmid, Philipp C. organization: Department of Chemistry, Energetic Materials Research, Ludwig Maximilian University, Butenandtstr. 5-13 (D), 81377 München (Germany) – sequence: 3 givenname: Simon surname: Schnell fullname: Schnell, Simon organization: Department of Chemistry, Energetic Materials Research, Ludwig Maximilian University, Butenandtstr. 5-13 (D), 81377 München (Germany) – sequence: 4 givenname: Jörg surname: Stierstorfer fullname: Stierstorfer, Jörg organization: Department of Chemistry, Energetic Materials Research, Ludwig Maximilian University, Butenandtstr. 5-13 (D), 81377 München (Germany)
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Snippet	A novel strategy for the design of energetic materials that uses fused amino‐substituted triazoles as energetic building blocks is presented. The... A novel strategy for the design of energetic materials that uses fused amino-substituted triazoles as energetic building blocks is presented. The...
SourceID	proquest pubmed crossref wiley istex
SourceType	Aggregation Database Index Database Enrichment Source Publisher
StartPage	9219
SubjectTerms	Alternative energy sources Cations Chemistry crystal structures energetic materials Friction Mathematical analysis Nitrates nitrogen Physicochemical properties Stability Stimuli Toxicity triazoles
Title	3,6,7-Triamino-[1,2,4]triazolo[4,3-b][1,2,4]triazole: A Non-toxic, High-Performance Energetic Building Block with Excellent Stability
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