journal article·2019-12-23

Energetic and Fluorescent Azole-Fused 4-Amino-1,2,3-triazine-3-N-oxides

Yongxing Tang, Gregory H. Imler, Damon A. Parrish, Jean’ne M. Shreeve

ACS Applied Energy Materials· Volume 2· Issue 12
Publisher page

Abstract

Nitrogen-rich heterocyclic fused molecules are of considerable significance in the fields of synthetic and materials chemistry. Here, an efficient strategy for the synthesis of azole fused 4-amino-1,2,3-triazine N-oxides (4-6) via the diazotization reactions of o-amino–aminohydroximoyl nitrogen-rich heterocyclic rings is reported. In addition, several energetic salts (7–12) based on these fused compounds were prepared. These compounds not only show promising properties as energetic materials but also exhibit green fluorescence due to the presence of the triazine N-oxide moiety. The mechanism of the ring-expansion reaction has been explored by the isolation and confirmation of compound 14. They have good detonation performance, especially the hydrazinium salt of 9 with a high density of 1.800 g cm–3, a detonation velocity of 9385 m s–1, as well as a detonation pressure of 33.6 GPa.
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Research context

OpenAlex topics: Energetic Materials and Combustion · Chemical Reactions and Mechanisms · Chemical Reaction Mechanisms

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

Affiliations

Department of Chemistry, University of Idaho, Moscow, Idaho 83844-2343 United States

Nanjing University of Science and Technology, Nanjing, Jiangsu 210094 China

Naval Research Laboratory, 4555 Overlook Avenue, Washington, D.C. 20375 United States

Funding

Office of Naval Research · Defense Threat Reduction Agency

References (32)

Show source-provided references
1. 10.1021/cr200039c10.1021/cr200039c ↗
2. 10.1021/ja103525v10.1021/ja103525v ↗
3. 10.1021/jacs.7b0878910.1021/jacs.7b08789 ↗
4. 10.1021/acsami.9b0836310.1021/acsami.9b08363 ↗
5. 10.1021/ja310384y10.1021/ja310384y ↗
6. 10.1021/ic400919n10.1021/ic400919n ↗
7. 10.1021/ja800712e10.1021/ja800712e ↗
8. 10.1021/cg501267f10.1021/cg501267f ↗
9. 10.1021/cg501048v10.1021/cg501048v ↗
10. 10.1021/jacs.5b0071410.1021/jacs.5b00714 ↗
11. 10.1021/acs.cgd.6b0140910.1021/acs.cgd.6b01409 ↗
12. 10.1038/s41467-018-04897-z10.1038/s41467-018-04897-z ↗
13. 10.1021/acsaem.9b0004910.1021/acsaem.9b00049 ↗
14. 10.1002/anie.20160872310.1002/anie.201608723 ↗
15. 10.1021/ja01497a05010.1021/ja01497a050 ↗
16. 10.3969/j.issn.1006-9941.2013.01.00510.3969/j.issn.1006-9941.2013.01.005 ↗
17. 10.1039/C5DT03044G10.1039/C5DT03044G ↗
18. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision E.01; Gaussian, Inc.: Wallingford, CT, 2004.
19. Sućeska, M. EXPLO5, version 6.01; Brodarski Institute, Zagreb, Croatia, 2013.
20. 2009
21. b13.4.2 Test 3 (a)(ii) BAM Fallhammer, pp 75.
22. c13.5.1 Test 3 (b)(i): BAM friction apparatus, pp 104.
23. 10.1021/ja00123a00110.1021/ja00123a001 ↗
24. 10.1021/jp070702b10.1021/jp070702b ↗
25. NIST Chemistry WebBook, NIST Standard Reference Database Number 69, June 2005, Linstrom, P. J., Mallard, W. G., Eds. National Institute of Standards and Technology: Gaithersburg, MD, 2005; pp 20899 (http://webbook.nist.gov).
26. Bruker. APEX3, v2015.5-2; Bruker AXS Inc.: Madison, Wisconsin, USA, 2015.
27. Bruker. SAINT, v8.34A; Bruker AXS Inc.: Madison, Wisconsin, USA, 2013.
28. Bruker. XPREP, v2014/2; Bruker AXS Inc.: Madison, Wisconsin, USA, 2014.
29. Bruker. SADABS, v2014/5; Bruker AXS Inc.: Madison, Wisconsin, USA, 2014.
30. Sheldrick, G. M. SHELXL-2014/7; University of Göttingen: Germany, 2014.
31. 10.1021/ja01603a03310.1021/ja01603a033 ↗
32. Keller G. · Bulletin de la Societe Chimique de France · 1975 · 1219