Molecular and Crystal Features of Thermostable Energetic Materials: Guidelines for Architecture of "bridged" Compounds

Hui Li, Lei Zhang*, Natan Petrutik, Kangcai Wang, Qing Ma, Daniel Shem-Tov, Fengqi Zhao, Michael Gozin

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


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.

Original languageEnglish
Pages (from-to)54-75
Number of pages22
JournalACS Central Science
Issue number1
StatePublished - 22 Jan 2020


FundersFunder number
Tel-Aviv University
National Natural Science Foundation of China11604017, 21603172


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