Thermal stabilization of energetic materials by the aromatic nitrogen-rich 4,4′,5,5′-tetraamino-3,3′-bi-1,2,4-triazolium cation

Journal of Materials Chemistry A

Volumn 3, Issue 6, 2015, Pages 2658-2668

  Klapötke, Thomas M ^a   Schmid, Philipp C ^a   Schnell, Simon ^a   Stierstorfer, Jörg ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; DIFFERENTIAL THERMAL ANALYSIS; ELECTRIC DISCHARGES; ELECTROSTATIC DEVICES; ELECTROSTATIC DISCHARGE; ELECTROSTATICS; EXPLOSIVES; FRICTION; INORGANIC COMPOUNDS; MASS SPECTROMETRY; NEGATIVE IONS; NITROGEN; POSITIVE IONS; SINGLE CRYSTALS; TEMPERATURE; THERMOANALYSIS; X RAY DIFFRACTION;

DETONATION PARAMETER; ELECTRICAL DISCHARGES; ENTHALPY OF FORMATION; ENVIRONMENTALLY BENIGN; HIGH TEMPERATURE STABILITY; SINGLE CRYSTAL X-RAY DIFFRACTION; TEMPERATURE STABLE; THERMAL STABILIZATION;

CHEMICAL COMPOUNDS;

EID: 84922110021     PISSN: 20507488     EISSN: 20507496     Source Type: Journal    
DOI: 10.1039/c4ta05964f     Document Type: Article

References (56)

1. (a) W. E. Bachmann and J. C. Sheehan, J. Am. Chem. Soc., 1949, 71, 1842-1845;
2. (b) E. P. Burrows and E. E. Brueggemann, J. Chromatogr., 1985, 329, 285-289;
3. (c) A. T. Nielsen, A. P. Chafin, S. L. Christian, D. W. Moore, M. P. Nadler, R. A. Nissan, D. J. Vanderah, R. D. Gilardi, C. F. George and J. L. Flippen-Anderson, Tetrahedron, 1998, 54, 11793-11812.
4. T. Fendt, N. Fischer, T. M. Klapötke and J. Stierstorfer, Inorg. Chem., 2011, 50, 1447-1458.
5. (a)H. Gao and J.M. Shreeve, Chem. Rev., 2011, 111, 7377-7436;
6. (b) R. Haiges, S. Schneider, T. Schroer and K. O. Christe, Angew. Chem., 2004, 116, 5027-5032;
7. Angew. Chem., Int. Ed., 2004, 43, 4919-4924;
8. (c) D. E. Chavez, M. A. Hiskey, D. L. Naud and D. Parrish, Angew. Chem., 2008, 120, 8431-8433;
9. Angew. Chem., Int. Ed., 2008, 47, 8307-8309;
10. (d) M. B. Talawar, R. Sivabalan, T. Mukundan, H. Muthurajan, A. K. Sikder, B. R. Gandhe and A. Subhananda Rao, J. Hazard. Mater., 2009, 161, 589-607;
11. (e) O. S. Bushuyev, P. Brown, A. Maiti, R. H. Gee, G. R. Peterson, B. L. Weeks and L. J. Hope-Weeks, J. Am. Chem. Soc., 2012, 134, 1422-1425;
12. (f) C. Li, L. Liang, K. Wang, C. Bian and J. Zhang, J. Mater. Chem. A, 2014, 2, 18097-18105.
13. (a) D. Fischer, T. Klapötke and J. Stierstorfer, Angew. Chem., 2014, 126, 8311-8314;
14. Angew. Chem., Int. Ed., 2014, 53, 8172-8175;
15. (b) M. Göbel and T. M. Klapötke, Z. Anorg. Allg. Chem., 2007, 633, 1006-1017;
16. (c) M. Härtel, T. M. Klapötke, D. Piercey and J. Stierstorfer, Z. Anorg. Allg. Chem., 2012, 638, 2008-2014.
17. T. M. Klapötke, P. Mayer, C. M. Sabaté, J. M. Welch and N. Wiegand, Inorg. Chem., 2008, 47, 6014-6027.
18. D. E. Chavez, M. A. Hiskey and R. D. Gilardi, Angew. Chem., 2000, 112, 1861-1863;
19. Angew. Chem., Int. Ed., 2000, 39, 1791-1793.
20. (a) A. Hammerl, M. A. Hiskey, G. Holl, T. M. Klapötke, K. Polborn, J. Stierstorfer and J. J. Weigand, Chem. Mater., 2005, 17, 3784-3793;
21. (b) L. Liang, K. Wang, C. Bian, L. Ling and Z. Zhou, Chem.-Eur. J., 2013, 19, 14902-14910;
22. (c) L. Liang, H. Huang, K. Wang, C. Bian, J. Song, L. Ling, F.- Zhao and Z. Zhou, J. Mater. Chem., 2012, 22, 21954-21964.
23. (a) A. A. Dippold and T. M. Klapötke, J. Am. Chem. Soc., 2013, 135, 9931-9938;
24. (b) J. Zhang and J. M. Shreeve, J. Am. Chem. Soc., 2014, 136, 4437-4445;
25. (c) M. Göbel, K. Karaghiosoff, T. M. Klapötke, D. G. Piercey and J. Stierstorfer, J. Am. Chem. Soc., 2010, 132, 17216-17226;
26. (d) J. Song, Z. Zhou, X. Dong, H. Huang, D. Cao, L. Liang, K. Wang, J. Zhang, F. Chen and Y. Wu, J. Mater. Chem., 2012, 22, 3201-3209.
27. R. Centore, A. Carella and S. Fusco, Struct. Chem., 2011, 22, 1095-1103.
28. H. Östmark, U. Bemm, A. Lenglet, R. Sandén and N. Wingborg, J. Energ. Mater., 2000, 18, 123-138.
29. R. J. Schmidt, J. C. Battaro and P. E. Penwell, The Development of New Protecting/Leaving Groups and Application to the Synthesis of Cage Nitramines, SRI International Project 6654, ADA261496, 1993.
30. A. Dippold and T. M. Klapötke, Chem.-Eur. J., 2012, 18, 16742-16753.
31. A. A. Dippold and T. M. Klapötke, Chem.-Asian J., 2013, 8, 1463-1471.
32. A. Rheingold, J. Cronin and T. Brill, Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 1987, 43, 402-404.
33. A. Katrusiak, Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 1994, 50, 1161-1163.
34. S. H. Kim and J. S. Kim, Bull. Korean Chem. Soc., 2013, 34, 2503-2506.
35. T. M. Klapötke, A. Preimesser and J. Stierstorfer, Z. Anorg. Allg. Chem., 2012, 638, 1278-1286.
36. N. Fischer, D. Fischer, T. M. Klapötke, D. G. Piercey and J. Stierstorfer, J. Mater. Chem., 2012, 22, 20418-20422.
37. N. Fischer, T. Klapötke, M. Reymann and J. Stierstorfer, Eur. J. Inorg. Chem., 2013, 2167-2180.
38. J. P. Agrawal, High Energy Materials, Wiley-VCH, Weinheim, 1st edn, 2010, p. 189.
39. K. Shipp, J. Org. Chem., 1964, 29, 2620-2623.
40. H. Östmark, A. Helte, T. Carlsson, R. Adolfsson, L. Bodin, C. Eldstäter, H. Edvinsson, J. Lundgreen and H. Örnhed, FOI Technical Report, N-guanylurea dinitramide (FOX-12): properties 2007, FOI-R-2312-SE, Project no. E20503.
41. T. M. Klapötke, J. Stierstorfer and A. U. Wallek, Chem. Mater., 2008, 20, 4519-4530.
42. D. Fischer, private communication.
43. M. Göbel and T. M. Klapötke, Z. Anorg. Allg. Chem., 2007, 633, 1006-1017.
44. (a) T. M. Klapötke and J. Stierstorfer, Chem. Phys., 2008, 10, 4340-4346;
45. (b) T.M. Klapötke and J. Stierstorfer, Eur. J. Inorg. Chem., 2008, 26, 4055-4062;
46. (c) T. M. Klapötke and J. Stierstorfer, Dalton Trans., 2009, 4, 643-653;
47. (d) T. M. Klapötke, F. A. Martin, N. T. Mayr and J. Stierstorfer, Z. Anorg. Allg. Chem., 2010, 636, 2555-2564;
48. (e) J. C. Oxley, J. L. Smith and H. Chen, Thermochim. Acta, 2002, 384, 91-99.
49. U. Teipel, T. Heintz and H. H. Krause, Propellants, Explos., Pyrotech., 2000, 25, 81-85.
50. J. Köhler and R. Meyer, Explosivstoffe, Wiley-VCH, Weinheim, 9th edn, 1998, pp. 166-168.
51. M. Sućeska, EXPLO5.06 program, Zagreb, Croatia, 2013.
52. C. Xue, J. Sun, B. Kang, Y. Liu, X. Liu, G. Song and Q. Xue, Propellants, Explos., Pyrotech., 2010, 35, 333-338.
53. G. I. Sunahara, S. Dodard, M. Sarrazin, L. Paquet, G. Ampleman, S. Thiboutot, J. Hawari and A. Y. Renoux, Ecotoxicol. Environ. Saf., 1998, 39, 185-194.
54. (a) M. Hesse, H. Meier and B. Zeeh, Spektroskopische Methoden in der Organischen Chemie, Thieme, Stuttgart, New York, 7th edn, 2005;
55. (b) G. Socrates, Infrared and Raman Characteristic Group Frequencies: Tables and Charts, John Wiley & Sons, Chichester, 3rd edn, 2004.
56. Y. Murtim, R. Agnihotri and D. Pathak, Am. J. Chem., 2011, 1, 42-46.