Citation: Zhai Lianjie, Zhang Junlin, Zhang Jiarong, Wu Minjie, Bi Fuqiang, Wang Bozhou. Progress in Synthesis and Properties of High Energy Density Compounds Regulated by N—F Bond[J]. Chinese Journal of Organic Chemistry, ;2020, 40(6): 1484-1501. doi: 10.6023/cjoc202001018 shu

Progress in Synthesis and Properties of High Energy Density Compounds Regulated by N—F Bond

Zhai Lianjie ^a,b ,
Zhang Junlin ^a,b ,
Zhang Jiarong ^a,b ,
Wu Minjie ^a,b ,
Bi Fuqiang ^a,b,, ,
Wang Bozhou ^a,b,,

a.
Xi'an Modern Chemistry Research Instritute, Xi'an 710065
b.
State Key Laboratory of Fluorine & Nitrogen Chemical, Xi'an 710065

Corresponding author: Bi Fuqiang, bifuqiang@gmail.com Wang Bozhou, wbz600@163.com
Received Date: 12 January 2020
Revised Date: 27 February 2020
Available Online: 6 March 2020
Fund Project: Project supported by the National Natural Science Foundation of China (No. 21805224)the National Natural Science Foundation of China 21805224

Figures(37)

Compared with the traditional N-O bond-based energetic materials, N-F bond-regulated energetic materials have received worldwide research interest due to their special features of high density, high specific impulse, and high heat release upon combustion with metals. The N-F bond-regulated energetic materials are classified as N-F azoles, (difluoroamino)dinitromethyl-substituted derivatives, gem-bis(difluoramino)-substituted derivatives, and difluoroamino polymers according to their structural characteristics. The recent developments of N-F bond and difluoramino (NF₂) energetic derivatives are reviewed. The construction methodologies of N-F bond and difluoroamino groups as well as the synthetic routes to their energetic derivatives are emphatically reviewed. Moreover, the physicochemical and energetic properties of some typical compounds are briefly introduced. It will be the inevitable trend to develop effective, safe, and simple N-F bond and difluoraminiation preparation method, and novel high-performing N-F bond-based azoles and cyclic difluoramino-nitramines with moderate sensitivities and stable structures.
- energetic materials,
- N-F bond compounds,
- difluoramino group,
- synthesis,
- detonation performances
1. [1]
  Gao, H.; Shreeve, J. M. Chem. Rev. 2011, 111, 7377. doi: 10.1021/cr200039c
2. [2]
  Klapötke, T. M. Chemistry of High-energy Materials, 2nd ed., Walter de Gruyter, Berlin, 2012.
3. [3]
  Badgujar, D. M.; Talawar, M. B.; Asthana, S. N.; Mahulikar, P. P. J. Hazard. Mater. 2008, 151, 289. doi: 10.1016/j.jhazmat.2007.10.039
4. [4]
  Xue, Q.; Bi, F. Q.; Zhang, J. R.; Zhang, J. L.; Wang, B. Z.; Zhang, S. R. Chin. J. Org. Chem. 2019, 39, 1244 (in Chinese).
5. [5]
  Wang, Y.; Liu, Y. J.; Song, S. W.; Yang, Z. J.; Qi, X. J.; Wang, K. C.; Liu, Y.; Zhang, Q. H.; Tian, Y. Nat. Commun. 2018, 9, 2444. doi: 10.1038/s41467-018-04897-z
6. [6]
  Tang, Y. X.; Kumar, D.; Shreeve, J. M. J. Am. Chem. Soc. 2017, 139, 13684. doi: 10.1021/jacs.7b08789
7. [7]
  Zhai, L. J.; Bi, F. Q.; Huo, H.; Luo, Y. F.; Li, X. Z.; Chen, S. P.; Wang, B. Z. Front. Chem. 2019, 7, 559. doi: 10.3389/fchem.2019.00559
8. [8]
  Zhang, J. R.; Bi, F. Q.; Lian, P.; Zhang, J. L.; Wang, B. Z. Chin. J. Org. Chem. 2017, 37, 2736 (in Chinese).
9. [9]
  Li, Y. L.; Xue, M.; Wang J. L.; Cao, D. L.; Ma, Z. L. Chin. J. Org. Chem. 2016, 36, 1528 (in Chinese).
10. [10]
  Zhou, J.; Zhang, J. L.; Ding, L.; Bi, F. Q.; Wang, B. Z. Chin. J. Energ. Mater. 2019, 27, 708 (in Chinese). doi: 10.11943/CJEM2018302
11. [11]
  Zhou, J.; Zhang, J. L.; Ding, L.; Bi, F. Q.; Wang, B. Z. Chin. J. Explos. Propellants 2019, 42, 608 (in Chinese).
12. [12]
  Zhai, L. J.; Bi, F. Q.; Luo, Y. F.; Wang, N. X.; Zhang, J. L.; Wang, B. Z. Sci. Rep. 2019, 9, 4321. doi: 10.1038/s41598-019-39723-z
13. [13]
  Xu, Y. G.; Shen, C.; Lin, Q. H.; Wang, P. C.; Jiang, C.; Lu, M. J. Mater. Chem. A 2016, 4, 17791. doi: 10.1039/C6TA08831G
14. [14]
  Barton, L. M.; Edwards, J. T.; Johnson, E. C.; Bukowski, E. J.; Sausa, R. C.; Byrd, E. F. C.; Orlicki, J. A.; Sabatini, J. J.; Baran, P. S. J. Am. Chem. Soc. 2019, 141, 12531. doi: 10.1021/jacs.9b06961
15. [15]
  Zhai, L. J.; Bi, F. Q.; Luo, Y. F.; Sun, L.; Huo, H.; Zhang, J. C.; Zhang, J. L.; Wang, B. Z.; Chen, S. P. Chem. Eng. J. 2020, 391, 123573. doi: 10.1016/j.cej.2019.123573
16. [16]
  Vishnevskiy, Y. V.; Tikhonov, D.; Schwabedissen, J.; Stammler, H-G.; Moll, R.; Krumm, B.; Klapötke, T. M.; Mitzel, N. W. Angew. Chem., Int. Ed. 2017, 56, 9619.
17. [17]
  Yu, Q.; Yin, P.; Zhang, J. H.; He, C. L.; Imler, G. H.; Parrish, D. A.; Shreeve, J. M. J. Am. Chem. Soc. 2017, 139, 8816. doi: 10.1021/jacs.7b05158
18. [18]
  Lukin, K. A.; Li, J.; Eaton, P. E.; Kanomata, N.; Hain. J.; Punzalan, E.; Gilardi, R. J. Am. Chem. Soc. 1997, 119, 9591. doi: 10.1021/ja970552q
19. [19]
  Zhang, M. X.; Eaton, P. E.; Gilardi, R. Angew. Chem., Int. Ed. 2000, 39, 401. doi: 10.1002/(SICI)1521-3773(20000117)39:2<401::AID-ANIE401>3.0.CO;2-P
20. [20]
  Gong, X. B.; Sun, C. H.; Pang, S. P.; Zhang, J.; Li, Y. C.; Zhao, X. Q. Chin. J. Org. Chem. 2012, 32, 486 (in Chinese).
21. [21]
  Nair, U. R.; Sivabalan, R.; Gore, G. M.; Geetha, M.; Asthana S. N.; Singh, H. Combust., Explos. Shock Waves 2005, 41, 121. doi: 10.1007/s10573-005-0014-2
22. [22]
  Ammon, H. L. Struct. Chem. 2001, 12, 205. doi: 10.1023/A:1016607906625
23. [23]
  Feng, Z. G. Prog. Chem. 2000, 12, 171 (in Chinese). doi: 10.3321/j.issn:1005-281X.2000.02.006
24. [24]
  Liu, H.; Zhang, Y. J.; Zhang, L. Y.; Zheng, W. F.; Pan, R. M. Chin. J. Explos. Propellants 2019, 42, 363 (in Chinese).
25. [25]
  Yetter, R. A.; Dryer, F. L.; Rabitz, H.; Brown, R. C.; Kolb, C. E. Combust. Flame 1998, 112, 387. doi: 10.1016/S0010-2180(97)00123-5
26. [26]
27. [27]
  Valluri, S. K.; Schoenitz, M.; Dreizin, E. Def. Technol. 2019, 15, 1.
28. [28]
  Li, S. W.; Zhao, F. Q.; Yuan, C.; Luo, Y.; Gao, Y. J. Solid Rocket Technol. 2002, 25, 36 (in Chinese). doi: 10.3969/j.issn.1006-2793.2002.02.009
29. [29]
  Chapman, R. D. Struct. Bonding 2007, 125, 123.
30. [30]
  Li, H.; Qin, Y. J.; Li, J. H.; Pan, R. M.; Wang, W. J. Chem. Bull. 2012, 75, 1076 (in Chinese).
31. [31]
  Klapötke, T. M. J. Fluorine Chem. 2006, 127, 679. doi: 10.1016/j.jfluchem.2006.03.001
32. [32]
  Chen, J. F.; Yu, Y.; Li, Y. C.; Pang, S. P. J. Fluorine Chem. 2018, 205, 35. doi: 10.1016/j.jfluchem.2017.11.008
33. [33]
  Ruff, O.; Giese, M. Eur. J. Inorg. Chem. 1936, 69, 598.
34. [34]
  Davenas, A. J. Propul. Power 2003, 19, 1108.
35. [35]
  Petry, R. C.; Freeman, J. P. J. Org. Chem. 1967, 32, 4034 doi: 10.1021/jo01287a068
36. [36]
  Coon, C. L.; Ross, D. L. US 3732288, 1973.
37. [37]
  Reed, S. F.; Shoults, R. D. J. Org. Chem. 1972, 37, 3326. doi: 10.1021/jo00986a027
38. [38]
  Coon, C. L.; Ross, D. L. US 3714254, 1973.
39. [39]
  Wiener, C.; Tyler, W. E. US 4128583, 1978.
40. [40]
  Zheng, Y. Y.; Zhou, J. Z.; Zhou, D. L.; Zhang, M. N. Acta Armamentarii 1988, 1, 59 (in Chinese).
41. [41]
  Wang, W. J.; Li, H.; Pan, R. M.; Zhu, W. H. Chin. J. Org. Chem. 2019, 39, 170 (in Chinese).
42. [42]
  Li, H.; Zhang, L. Y.; Pan, R. M.; Wang, W. J. Chin. J. Explos. Propellants. 2012, 35, 37 (in Chinese).
43. [43]
  Zhang, M. Q.; Liu, H. Y.; Gao, B. Z.; Zhang, L.; Kang, L.; Zhang, K. R. Chin. J. Energ. Mater. 2012, 20, 314 (in Chinese). doi: 10.3969/j.issn.1006-9941.2012.03.011
44. [44]
  Laali, K. K.; Tanaka, M.; Forohar, F.; Cheng, M.; Fetzer, J. C. J. Fluorine Chem. 1998, 91, 185. doi: 10.1016/S0022-1139(98)00224-3
45. [45]
  Dalinger, I. L.; Shkineva, T. K.; Vatsadze, I. A.; Popova, G. P.; Shevelev, S. A. Mendeleev Commun. 2011, 21, 48. doi: 10.1016/j.mencom.2011.01.020
46. [46]
  Grakauskas, V.; Baum, K. J. Org. Chem. 1969, 34, 2840. doi: 10.1021/jo01262a010
47. [47]
  Chapman, R. D.; Davis, M. C.; Gilardi, R. Synth. Commun. 2003, 35, 4173.
48. [48]
  Sharts, C. M. J. Org. Chem. 1968, 33, 1008. doi: 10.1021/jo01267a014
49. [49]
  Mcpake, C. B.; Murray, C. B.; Sandford, G. Aust. J. Chem. 2013, 66, 145. doi: 10.1071/CH12381
50. [50]
  Archibald, T. G.; Manser, G. E. US 5789617, 1998.
51. [51]
  Emelexus, H. J.; Shreeve, J. M.; Verma, R. D. Adv. Inorg. Chem. 1989, 33, 139. doi: 10.1016/S0898-8838(08)60195-6
52. [52]
  Klapdor, M. F.; Willner, H.; Poll, W.; Mootz, D. Angew. Chem. 1996, 108, 320. doi: 10.1002/ange.19961080309
53. [53]
  Freeman, J. P.; Kennedy, A.; Colburn, C. B. J. Am. Chem. Soc. 1960, 82, 5304. doi: 10.1021/ja01505a009
54. [54]
  Petry, R. C.; Freeman, J. P. J. Am. Chem. Soc. 1961, 83, 3912.
55. [55]
  Graham, W. H.; Parker, C. O. J. Org. Chem. 1963, 28, 850.
56. [56]
  Grakauskas, V.; Baum, K. J. Am. Chem. Soc. 1970, 92, 2096. doi: 10.1021/ja00710a050
57. [57]
  Banks, R. E.; Haszeldine, R. N.; Lalu, J. P. J. Chem. Soc., C 1966, 1514. doi: 10.1039/j39660001514
58. [58]
  Baum, K. J. Am. Chem. Soc. 1968, 90, 7083. doi: 10.1021/ja01027a035
59. [59]
  Fokin, A. V.; Kosyrev, Y. M.; Shevchenko, V. I. Russ. Chem. Bull. 1983, 31, 1626.
60. [60]
  Graham, W. H.; Freeman, J. P. J. Am. Chem. Soc. 1967, 89, 716. doi: 10.1021/ja00979a058
61. [61]
  Keith, J. N.; Douthart, R. J.; Sumida, W. K.; Solomon, I. J. Advanced Propellant Chemistry 1966, 141.
62. [62]
  Haiges, R.; Wagner, R.; Boatz, J. A.; Yousufuddin, M.; Etzkorn, M.; Surya Prakash, G. K.; Christe, K. O.; Chapman, R. D.; Welker, M. F.; Kreutzberger. C. B. Angew. Chem., Int. Ed. 2006, 45, 5179. doi: 10.1002/anie.200601020
63. [63]
  Coon, C. L.; Hill, M. E.; Ross, D. L. US 3759998, 1973.
64. [64]
  Baum, K.; Grakauskas, V. US 4075246, 1978.
65. [65]
  Flanagan, G. E.; Frankel, M. B.; Witucki, E. F. US 4141910, 1979.
66. [66]
  Surya Prakash, G. K.; Etzkorn, M.; Olah, G. A.; Christe, K. O.; Schneidera, S.; Vij, A. Chem. Commun. 2002, 1712.
67. [67]
  Lustig, M.; Cady, G. H. Inorg. Chem. 1963, 2, 388. doi: 10.1021/ic50006a036
68. [68]
  Fokin, A. K.; Studnev, Y. N.; Rapkin, A. L.; Kuznetsova, L. D. Russ. Chem. Bull. 1996, 45, 2547. doi: 10.1007/BF01431113
69. [69]
  Dalinger, I. L.; Shakhnes, A. K.; Monogarov, K. A.; Suponitsky, K. Y.; Sheremetev, A. B. Mendeleev Commun. 2015, 25, 429. doi: 10.1016/j.mencom.2015.11.010
70. [70]
  Semenov, V. V.; Shevelev, S. A.; Bruskin, A. B.; Shakhnes, A. K.; Kuz'min, V. S. Chem. Heterocycl. Compd. 2017, 53, 728.
71. [71]
  Dalinger, I. L.; Kormanov, A. V.; Suponitsky, K. Yu.; Muravyev, N. V.; Sheremetev, A. B. Chem. Asian J. 2018, 13, 1165.
72. [72]
  Colburn, C. B.; Kennedy, A. J. Am. Chem. Soc. 1958, 80, 5004.
73. [73]
  Baumgardner, C. L.; Lawton, E. L. Acc. Chem. Res. 1974, 7, 14. doi: 10.1021/ar50073a003
74. [74]
  Reed Jr, S. F. J. Org. Chem. 1968, 33, 1861. doi: 10.1021/jo01269a034
75. [75]
  Petry, R. C.; Parker, C. O.; Johnson, F. A.; Stevens, T. E.; Freeman, J. P. J. Org. Chem. 1967, 32, 1534. doi: 10.1021/jo01280a052
76. [76]
  Petry, R. C.; Freeman, J. P. J. Am. Chem. Soc. 1961, 83, 3912.
77. [77]
  Gakh, A. A.; Romaniko, S. V.; Ugrak, B. I.; Fainzilberg, A. A. Tetrahedron 1991, 47, 7447. doi: 10.1016/S0040-4020(01)89746-5
78. [78]
  Majumder, U.; Armantrout, J. R.; Williams, R. V.; Shreeve, J. M. J. Org. Chem. 2002, 67, 8435. doi: 10.1021/jo026201y
79. [79]
  Belter, R. K. J. Fluorine Chem. 2012, 132, 961.
80. [80]
  Dalinger, I. L.; Vinogradov, V. M.; Shevelev, S. A.; Kuz'min, V. S.; Arnautova, E. A.; Pivina, T. S. Propellants, Explos., Pyrotech. 1998, 23, 212. doi: 10.1002/(SICI)1521-4087(199808)23:4<212::AID-PREP212>3.0.CO;2-Y
81. [81]
  Fokin, A. K.; Studnev, Y. N.; Stolyarov, V. P.; Mel'nikov, A. A. Russ. Chem. Bull. 2000, 49, 949. doi: 10.1007/BF02494724
82. [82]
  Marsden, H. M.; Shreeve, J. M. Inorg. Chem. 1987, 26, 169. doi: 10.1021/ic00248a033
83. [83]
  John, E. O.; Shreeve, J. M. Inorg. Chem. 1988, 27, 3100. doi: 10.1021/ic00291a011
84. [84]
  John, E. O.; Kirchmeier, R. L.; Shreeve, J. M. J. Fluorine Chem. 1990, 47, 333. doi: 10.1016/S0022-1139(00)82383-0
85. [85]
  John, E. O.; Willett, R. D.; Scott, B.; Kirchmeier, R. L.; Shreeve, J. M. Inorg. Chem. 1989, 28, 893. doi: 10.1021/ic00304a018
86. [86]
  Ye, C. f.; Gao, H. X.; Shreeve, J. M. J. Fluorine Chem. 2007, 128, 1410. doi: 10.1016/j.jfluchem.2007.07.006
87. [87]
  Litvinov, B. V.; Fainzil'berg, A. A.; Pipekin, V. I.; Smirnov, S. P.; Loboiko, B. G.; Shevelev, S. A.; Nazin, G. M. Dokl. Akad. Nauk 1994, 336, 67.
88. [88]
  Khisamutdinov, G. K.; Shevelev, S. A. Russ. Chem. Bull., Int. Ed. 2001, 50, 736. doi: 10.1023/A:1011345819626
89. [89]
  Fokin, A. V.; Studnev, Y. N.; Kuznetsova, L. D. Dokl. Akad. Nauk 1996, 3, 358
90. [90]
  Fokin, A. V.; Studnev, Y. N.; Kuznetsova, L. Russ. Chem. Bull. 1996, 45, 1952. doi: 10.1007/BF01457784
91. [91]
  Zhang, M. Q.; Liu, H. Y, ; Wei, X. C.; Zhang, L.; Kang, L. Chem. Propellants Polym. Mater. 2017, 15, 45 (in Chinese).
92. [92]
  Frankel, M. B.; Witucki, E. F. US 4341712, 1982.
93. [93]
  Adolph, H. G.; Trivedi, N. J. US 6325876 B1, 2001.
94. [94]
  Ammon, H. L.; Holden, J. R.; Du, Z. Structure and Density Predictions for Energetic Materials, 2002. http://www.chem.missouri.edu/thompson/MURI02/extended/Ammon_MURI_extended_abstract_4.pdf.
95. [95]
  Baum, K.; Trivedi, N. J.; Lovato, J. M.; Iyer, V. K. Report NRO-1-1 (final), Fluorochem, Azusa, CA, 1993.
96. [96]
  Chapman, R. D.; Welker, M. F; Kreutzberger, C. B. J. Org. Chem. 1998, 63, 1566. doi: 10.1021/jo9718399
97. [97]
  Chapman, R. D.; Gilardi, R. D.; Welker, M. F.; Kreutzberger, C. B. J. Org. Chem. 1999, 64, 960. doi: 10.1021/jo9819640
98. [98]
  Chapman, R. D.; Groshens, T. J. US 7563889 B1, 2009.
99. [99]
  Chapman, R. D.; Groshens, T. J. US 8444783 B1, 2013.
100. [100]
  Axenrod, T.; Guan, X. P.; Sun, J. G.; Qi, L.; Chapman, R. D.; Gilardi, R. D. Tetrahedron Lett. 2001, 42, 2621. doi: 10.1016/S0040-4039(01)00260-X
101. [101]
  Chapman, R. D.; Nguyen, B. V. US 6310204 B1, 2001.
102. [102]
  Li, H. Ph.D. Dissertation, Nanjing University of Science & Technology, Nanjing, 2015 (in Chinese).
103. [103]
  Mei, Y. M.S. Thesis, Nanjing University of Science & Technology, Nanjing, 2016 (in Chinese).
104. [104]
  Archibald, T. G.; Manser, G. E. Immoos, J. E. US 5240311, 1995.
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2. [2]
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  Yunxin Xu , Wenbo Zhang , Jing Yan , Wangchang Geng , Yi Yan . A Fascinating Saga of “Energetic Materials”. University Chemistry, 2024, 39(9): 266-272. doi: 10.3866/PKU.DXHX202307008
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19. [19]
  Zhen Yao , Bing Lin , Youping Tian , Tao Li , Wenhui Zhang , Xiongwei Liu , Wude Yang . Visible-Light-Mediated One-Pot Synthesis of Secondary Amines and Mechanistic Exploration. University Chemistry, 2024, 39(5): 201-208. doi: 10.3866/PKU.DXHX202311033
20. [20]
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沈阳化工大学材料科学与工程学院沈阳 110142