Synthesis and Thermal Stability of New Polynitrostilbenes

Wei, Jianping; Li, Fangmei; Xu, Junhui; Peng, Xinhua

doi:10.1071/ch14400

Cited by 2 publications

(4 citation statements)

References 23 publications

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“…The highest probability of an EM to be thermostable was found in explosives having HBP in the relatively narrow range 50–70%. The latter group of explosives includes single-ring compounds, such as A4 (TATB), A15 (ANPZ), A13 (DADNPO), and A14 (LLM105), as well as some bridged EMs, such as D5 (TKX55), E9 , D7 , and D9 …”

Section: Dft Calculationsmentioning

confidence: 99%

“…The latter group of explosives includes single-ring compounds, such as A4 (TATB), A15 (ANPZ), A13 (DADNPO), and A14 (LLM105), as well as some bridged EMs, such as D5 (TKX55), E9, 47 D7, 41 and D9. 43 Our further analysis of correlation between EMs' HBAs and their thermostability showed that heat-resistant explosives prevalently have HBA values in a range between 90 and 180 Å 2 (Figure 23). Grouping compounds with similar HBA and thermostability properties together, we could draw three different clusters for each of HL3, HL7, and HL9 explosives.…”

Section: ■ Introductionmentioning

confidence: 99%

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Molecular and Crystal Features of Thermostable Energetic Materials: Guidelines for Architecture of “Bridged” Compounds

et al. 2019

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Extensive density functional theory (DFT) calculation and data analysis on molecular and crystal level features of 60 reported energetic materials (EMs) allowed us to define key descriptors that are characteristics of these compounds' thermostability. We see these descriptors as reminiscent of "Lipinski's rule of 5", which revolutionized the design of new orally active pharmaceutical molecules. The proposed descriptors for thermostable EMs are of a type of molecular design, location and type of the weakest bond in the energetic molecule, as well as specific ranges of oxygen balance, crystal packing coefficient, Hirshfeld surface hydrogen bonding, and crystal lattice energy. On this basis, we designed three new thermostable EMs containing bridged, 3,5-dinitropyrazole moieties, HL3, HL7, and HL9, which were synthesized, characterized, and evaluated in small-scale field detonation experiments. The best overall performing compound HL7 exhibited an onset decomposition temperature of 341 °C and has a density of 1.865 g cm −3 , and the calculated velocity of detonation and maximum detonation pressure were 8517 m s −1 and 30.6 GPa, respectively. Considering HL7's impressive safety parameters [impact sensitivity (IS) = 22 J; friction sensitivity (FS) = 352; and electrostatic discharge sensitivity (ESD) = 1.05 J] and the results of small-scale field detonation experiments, the proposed guidelines should further promote the rational design of novel thermostable EMs, suitable for deep well drilling, space exploration, and other high-value defense and civil applications.

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Section: Dft Calculationsmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Molecular and Crystal Features of Thermostable Energetic Materials: Guidelines for Architecture of “Bridged” Compounds

et al. 2019

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“…The absorption peaks at around 270 and 370 nm were primarily due to the π–π* transition and the n –π* transition. [ 33 ] All 12 catalysts exhibited strong absorption peaks at 450 nm, which was due to the replacement of hydrogen on the benzene ring by the group containing n electrons on the para position. [ 34 ] It enhanced the conjugation of n –π* and shifted the absorption wavelength to the long‐wave direction.…”

Section: Resultsmentioning

confidence: 99%

“…At the first attempt, we tried to prepare the target catalysts according to a previously reported method, [32,33] but many mixtures were obtained. Then, we optimized the methods of their synthesis such as setting the size of the silica gel to 37-48 μm.…”

Section: Preparation Routementioning

confidence: 99%

Metal‐Free Hybrid Energetic Composites Based on Donor–Acceptor π‐Conjugated Organic Energetic Catalysts with Enlightening the Laser Ignition Performance of Multi‐Scale Ammonium Perchlorate

Tang

Yang

et al. 2023

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Photosensitive materials, such as energetic complexes, usually have high sensitivity and cause heavy‐metal pollution, whereas others, like carbon black and dye, do not contain energy, which affects energy output and mechanical properties. In this work, donor–acceptor π‐conjugated energetic catalysts, denoted as D‐n, are designed and synthesized. Nonmetallic hybrid energetic composites are prepared by assembling the as‐synthesized catalysts into multiscale ammonium perchlorate (AP). Composites containing catalysts and APs can be successfully ignited without the involvement of metals. The new ignition mechanism is further analyzed using experimental and theoretical analyses such as UV–vis‐near‐infrared (NIR) spectra, electron‐spin resonance spectroscopy, and energy‐gap analysis. The shortest ignition delay time is 56 ms under the experimental condition of a NIR wavelength of 1064 nm and a laser power of 10 W. At the voltage of 1 kV and the electric field of 500 V mm−1, the laser‐ignition delay time of D‐2/AP hybrid composite decreases from 56 to 35 ms because D‐2 also exhibits organic semiconductor‐like properties. D‐2/AP and D‐12/AP can also be used to successfully laser ignite other common energetic materials. This study can guide the development of advanced metal‐free laser‐ignitable energetic composites to address challenges in the field of aerospace engineering.

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Synthesis and Thermal Stability of New Polynitrostilbenes

Abstract: New polynitrostilbenes were directly synthesised by the Knoevenagel condensation of aromatic aldehydes with nitrotoluenes. The differential scanning calorimetry results demonstrated that the introduction of an amino group and C=C double bonds could improve the thermal stability.

Cited by 2 publications

References 23 publications

Molecular and Crystal Features of Thermostable Energetic Materials: Guidelines for Architecture of “Bridged” Compounds

Molecular and Crystal Features of Thermostable Energetic Materials: Guidelines for Architecture of “Bridged” Compounds

Metal‐Free Hybrid Energetic Composites Based on Donor–Acceptor π‐Conjugated Organic Energetic Catalysts with Enlightening the Laser Ignition Performance of Multi‐Scale Ammonium Perchlorate

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