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Molecular design and theoretical study of oxadiazole-bifurazan derivatives

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Abstract

Context

The design and synthesis of new high energy density materials is an important part of the research in the field of high energy materials. However, the synthesis of high-energy materials is very difficult and dangerous. Therefore, it is necessary to design the compounds in advance and evaluate the performance of the designed compounds, so as to screen the high-energy candidate compounds with excellent performance and provide reference for future synthesis and application. 1,2,5-oxadiazole (furazan) and 1,2,4-oxadiazole are five-membered nitrogen-oxygen heterocycles. Because their structures contain high-energy N-O, C=N bonds, they can effectively improve the energy density and oxygen balance of compounds, which has attracted widespread attention. In this paper, 42 kinds of oxadiazole-bifurazan energetic derivatives were designed by inserting different functional groups and changing the parent bridging groups with 1,2,4-oxadiazole and furazan as the basic structural units. Their electronic structures, aromaticity, heats of formation (HOFs), detonation properties, thermodynamic properties and electrostatic potential were systematically studied by density functional than theory (DFT). The results show that -C (NO2)3 has the greatest improvement effect on HOFs among all the substituent groups. The detonation performance of -N=N- bridged oxadiazole-bifurazan derivatives is better than that of -NH-NH- bridged derivatives. And -C(NO2)3 is the most effective group to improve the detonation performance and density of compounds. Compared with the parent compounds, when a -C(NO2)3 was introduced, the density increased by about 5.5%. A6 (D = 10.30 km·s-1, P = 48.86 GPa) and D6 (D = 9.57 km·s-1, P = 42.31 GPa) are the compounds with the best D and P among the designed compounds, which are higher than RDX and HMX, and are potential candidates for new high-energy materials.

Methods

With the help of Gaussian16 software and Multiwfn 3.8 package, the B3LYP method in density functional theory was selected. The 6-311G (d, p) basis set was used to optimize the structure of the 42 derivatives, and the high-precision def2-TZVPP basis set was used to calculate the energy.

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Data availability

We confirm the availability of all the data and materials in this manuscript. The manuscript has full control of all primary data, and the authors agree to allow the journal to review their data if requested.

Code availability

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Funding

This study was supported by the Natural Science Foundation of Jiangsu Province (NO. BK20220352). We are so grateful to the High Performance Computing Center of Nanjing Tech University for doing the numerical calculations in this paper on its x-Flex enterprise blade cluster system.

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Authors and Affiliations

  1. College of Safety Science and Engineering, Nanjing Tech University, Nanjing, 211816, China

    Jun Chen, Jiani Xu, Tingting Xiao, Meihua Zhao, Jun Cao, Peng Ma & Congming Ma

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  1. Jun Chen
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  2. Jiani Xu
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  3. Tingting Xiao
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Contributions

The manuscript was written through the contributions of all authors. Jun Chen: software, data curation, writing original draft. Jiani Xu and Tingting Xiao: formal analysis. Meihua Zhao and Jun Cao: investigation, validation. Peng Ma: resources, project administration. Congming Ma: conceptualization, methodology.

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Correspondence to Peng Ma.

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We allow the journal to review all the data, and we confirm the validity of theresults. There are no financial relationships. This work was not published previously, and it is not submitted to more than one journal. It is also not split up into several parts to submit. No data have been fabricated or manipulated.

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Chen, J., Xu, J., Xiao, T. et al. Molecular design and theoretical study of oxadiazole-bifurazan derivatives. J Mol Model 29, 175 (2023). https://doi.org/10.1007/s00894-023-05571-y

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