New Strategy for Enhancing Energetic Properties by Regulating Trifuroxan Configuration: 3,4-Bis(3-nitrofuroxan-4-yl)furoxan

Abstract

It is of current development to construct high–performance energetic compounds by aggregation of energetic groups with dense arrangement. In this study, a hydrogen-free high-density energetic 3,4-bis(3-nitrofuroxan-4-yl)furoxan (BNTFO-I) was designed and synthesized in a simple, and straightforward manner. Its isomer, 3,4-bis(4-nitrofuroxan-3-yl)furoxan (BNTFO-IV), was also obtained by isomerization. The structures of BNTFO-I and BNTFO-IV were confirmed by single-crystal X-ray analysis for the first time. Surprisingly, BNTFO-I has a remarkable calculated crystal density of 1983 g cm−3 at 296 K, which is distinctly higher than BNTFO-IV (1.936 g cm−3, 296 K), and ranks highest among azole-based CNO compounds yet reported. It is noteworthy that BNTFO-I exhibits excellent calculated detonation properties (vD, 9867 m s−1, P, 45.0 GPa). The interesting configuration differences of BNTFO-I and BNTFO-IV provide insight into the design of new advanced energetic materials.

1,2,5‐Oxadiazole‐Based High‐Energy‐Density Materials: Synthesis and Performance

“…The isomer of 3,4‐bis(4‐nitrofuroxan‐3‐yl)furoxan 182 ‐ 3 ,4‐bis(3‐nitrofuroxan‐4‐yl)furoxan 188 was recently prepared via a three‐step procedure from 3,4‐bis(oximinomethyl)furoxan 189 . Substrate 189 was transformed into 3‐nitro‐4‐cyanofuroxan 190 according to a known procedure, which then added hydroxylamine to give 4‐(aminohydroximino)‐3‐nitrofuroxan 191 .…”

“…It is noteworthy that compound 188 exhibits excellent detonation performance ( D =9867 m s −1 ; P =45.0 GPa). Curious configuration differences of HEDMs 188 and 182 provide insight into the design of new advanced energetic materials …”

Nitro-, Cyano-, and Methylfuroxans, and Their Bis-Derivatives: From Green Primary to Melt-Cast Explosives

“…Among a variety of energetic patterns considered for further functionalization, the 1,2,5-oxadiazole-2-oxide (often referred to as furoxan) ring is indeed prominent due to its attractive oxygen balance, high density of energetic derivatives, and high positive enthalpy of formation [ 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 ]. Although only two positions in the furoxan ring are available for the introduction of energetic substituents, the N -oxide regioisomerism is a promising strategy for tuning the detonation performance of furoxan-based energetic materials [ 19 , 20 , 21 , 22 ].…”

“…In the present study, we consider in detail the important methylfuroxan and nitrofuroxan structural motifs as functional explosophoric building blocks in the design of multipurpose energetic materials ( Figure 2 ). The cyanofuroxan fragment is also scrutinized due to its great importance as a functional moiety in the synthesis of various energetic materials [ 15 , 19 ]. It should be noted that information on the thermal, safety, and energetic properties for nitro-, cyano-, and methylfuroxans remains very limited.…”

“…Among various desired properties, high energy density materials are a long-sought goal for numerous ongoing research programs [1][2][3][4]. Moreover, traditional energetic materials, such as trinitrotoluene (TNT), hexogen (RDX), pentaerythritol tetranitrate (PETN), Molecules 2020, 25, 5836 2 of 19 and nitroglycerine (NG), suffer from inefficient and unsafe methods for their synthesis and limited environmental compatibility [5,6]. Therefore, the search for novel high-energy materials with balanced properties for a wide range of applications, while adhering to strict demands regarding safety and ecology concerns, remains highly urgent.…”