High-throughput design of energetic molecules

Liu, Jian; Zhao, Shicao; Duan, Bowen; He, Xudong; Yang, Chunming; Pu, Xuemei; Zhang, Xinben; Xiao, Yonghao; Nie, Fude; Qian, Wen; Li, Geng; Zhang, Chaoyang

doi:10.1039/d3ta05002e

Cited by 11 publications

(1 citation statement)

References 68 publications

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“…This also alerts us to carefully consider the individual atoms of both the substitutes and the skeleton when they serve as the exposed parts of a molecule to address the issues of intermolecular interaction, instead of a substitute or a skeleton as a whole. After all, in the era of high-throughput design of materials, the substituent and skeleton are the main bodies for constructing molecules and quantitative structure− property relationships; 23 therein, the importance of an individual atom may be overlooked.…”

Section: Introductionmentioning

confidence: 99%

2,4,6-Triazido-1,3,5-triazine and 2,5,8-Triazido-s-heptazine as Typical Planar Layer-Stacked Molecules with Identical Substituents Surrounding the Skeleton

Xue,

Zuo,

Guo

et al. 2024

Crystal Growth & Design

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In general, a planar molecule with identical substituents surrounding its skeleton can hardly be planar layer-stacked in a crystal under common conditions. This is because these identical substituents carry the same charge, and their close arrangement leads to intermolecular electrostatic repulsion. Exceptionally, 2,4,6-triazido-1,3,5-triazine (TATA) and 2,5,8-triazido-s-heptazine (TASHA) are such molecules each with three azido groups (−N 3 ) around the skeleton but still stacked in a pattern of planar layer. This paper discloses the underlying mechanism for the exception. It is found that the molecular edge of either TATA or TASHA is not always covered by negative electrostatic potentials (ESPs), different from common knowledge. That is, for TATA, the middle N atoms of the three −N 3 are positively charged and produce three positive ESP parts, and the remaining N atoms are charged reversely and present negative ones; thereby, positive and negative ESP regions alternately appear on the molecular edge, satisfying a necessary requirement of planar layered stacking. Thus, the seeming exception is not exceptional. This understanding is verified to be fit to other molecules like TATA and TASHA. Meanwhile, it alerts us to carefully consider individual atoms of both substituents and the skeleton of a molecule when they are exposed as the outmost parts to address intermolecular interaction related issues, instead of a substituent or a skeleton as a whole.

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Section: Introductionmentioning

confidence: 99%