Scholarlink

Context <p>Nitrogen-enriched aromatic fused heterocycles are a cornerstone of next-generation energetic materials, which are highly sought after for their high density and heat of formation. In this work, we present a computational design of six hydrogen-free energetic compounds based on heat-resistant, highly stable isomeric tetranitro-1,3a,6,6a-dibenzotetraazapentalene (<i>y</i>-TACOT) and tetranitro-1,3a,4,6a-dibenzotetraazapentalene (<i>z</i>-TACOT) frameworks, aiming to balance performance and sensitivity. To enhance the performance and energy content of the <i>y</i>-TACOT and <i>z-</i>TACOT frameworks while preserving their thermal stability and sensitivity, the two fused benzene rings in their structures were replaced with pyrazine, pyrimidine, and pyridazine.&#xa0;All the designed tetranitrodibenzo-tetraazapentalene (TACOT) derivatives are predicted to possess high enthalpies of formation (&gt; 774&#xa0;kJ/mol), high density (&gt; 1.86&#xa0;g/cm<sup>3</sup>), superior detonation pressure (&gt; 33.15 GPa), velocity (&gt; 8818&#xa0;m/s), heat of detonation (&gt; 1432&#xa0;cal/g), and high strength of C-NO<sub>2</sub> bonds (&gt; 200&#xa0;kJ/mol). Analysis of aromaticity, molecular planarity, and sphericity of the designed compounds yielded results comparable to those of parent <i>y</i>-TACOT and <i>z</i>-TACOT compounds, suggesting they will likely preserve key structural properties. With their collective profile of high-energy density, thermal stability, and low sensitivity, particularly evident in the pyridazine-based analogues, these compounds are promising candidates for next-generation heat-resistant applications with balanced performance and stability.</p> Methods <p>The optimization and energy calculations of designed tetracyclic compounds were carried out at the B3LYP/6-311G(d,p) level of theory, utilizing the Gaussian 09 software package. The molecular surface properties were analyzed using Multiwfn. The EXPLO5 (V7.01.01) thermochemical code was used to predict the detonation properties.</p> Graphical abstract <p></p>

错误：搜索内容不能为空，请输入英文关键词
错误：关键词超出字数限制，请精简
高级检索

Unveiling the potential of high-energy heat-resistant pyrazine, pyrimidine and pyridazine substituted tetranitrodibenzo-tetraazapentalene (TACOT) derivatives

  • 期刊论文

  • 发表日期：

    2026年6月3日

查看全文
  • Renu Rani,
  • Arzoo Gupta,
  • Vikas D. Ghule,
  • Srinivas Dharavath

摘要

Context

Nitrogen-enriched aromatic fused heterocycles are a cornerstone of next-generation energetic materials, which are highly sought after for their high density and heat of formation. In this work, we present a computational design of six hydrogen-free energetic compounds based on heat-resistant, highly stable isomeric tetranitro-1,3a,6,6a-dibenzotetraazapentalene (y-TACOT) and tetranitro-1,3a,4,6a-dibenzotetraazapentalene (z-TACOT) frameworks, aiming to balance performance and sensitivity. To enhance the performance and energy content of the y-TACOT and z-TACOT frameworks while preserving their thermal stability and sensitivity, the two fused benzene rings in their structures were replaced with pyrazine, pyrimidine, and pyridazine. All the designed tetranitrodibenzo-tetraazapentalene (TACOT) derivatives are predicted to possess high enthalpies of formation (> 774 kJ/mol), high density (> 1.86 g/cm3), superior detonation pressure (> 33.15 GPa), velocity (> 8818 m/s), heat of detonation (> 1432 cal/g), and high strength of C-NO2 bonds (> 200 kJ/mol). Analysis of aromaticity, molecular planarity, and sphericity of the designed compounds yielded results comparable to those of parent y-TACOT and z-TACOT compounds, suggesting they will likely preserve key structural properties. With their collective profile of high-energy density, thermal stability, and low sensitivity, particularly evident in the pyridazine-based analogues, these compounds are promising candidates for next-generation heat-resistant applications with balanced performance and stability.

Methods

The optimization and energy calculations of designed tetracyclic compounds were carried out at the B3LYP/6-311G(d,p) level of theory, utilizing the Gaussian 09 software package. The molecular surface properties were analyzed using Multiwfn. The EXPLO5 (V7.01.01) thermochemical code was used to predict the detonation properties.

Graphical abstract