TY - JOUR
T1 - Regioisomeric Control of Triexplosophoric Groups on a 1,2,4-Triazole Scaffold for an Enhanced Energy-Stability Balance
AU - Ding, Ning
AU - Guo, Pengcheng
AU - Jiang, Yanda
AU - Xu, Xudong
AU - Sun, Qi
AU - Li, Shenghua
AU - Pang, Siping
N1 - Publisher Copyright:
© 2025 American Chemical Society
PY - 2025/10/31
Y1 - 2025/10/31
N2 - Regioisomeric control is presented as a precise strategy to resolve the energy-stability conflict in trifunctionalized 1,2,4-triazole energetic materials. By positioning a stabilizing amino group adjacent to a highly energetic trinitromethyl group, a new molecule, 1-trinitromethyl-3-nitro-5-amino-1,2,4-triazole (TN-ANTA), was designed and synthesized. Compared to its reported isomer, TN-ANTA exhibits a superior combination of high density (1.905 g/cm3vs 1.878 g/cm3), enhanced thermal stability (Tdec= 128 °C vs 119 °C), and markedly improved impact sensitivity (7 J vs 1 J). Mechanistic studies reveal that this enhancement stems from a combination of more compact crystal packing, driven by stronger intermolecular interactions, and a higher bond dissociation energy of the weakest C-NO2bond due to intramolecular stabilization. The superiority of this design principle was further validated as the energetic salts of TN-ANTA also consistently displayed higher densities and thermal stabilities than their corresponding isomers. This work establishes regioisomeric placement of functional groups as a powerful approach for the rational design of advanced energetic materials.
AB - Regioisomeric control is presented as a precise strategy to resolve the energy-stability conflict in trifunctionalized 1,2,4-triazole energetic materials. By positioning a stabilizing amino group adjacent to a highly energetic trinitromethyl group, a new molecule, 1-trinitromethyl-3-nitro-5-amino-1,2,4-triazole (TN-ANTA), was designed and synthesized. Compared to its reported isomer, TN-ANTA exhibits a superior combination of high density (1.905 g/cm3vs 1.878 g/cm3), enhanced thermal stability (Tdec= 128 °C vs 119 °C), and markedly improved impact sensitivity (7 J vs 1 J). Mechanistic studies reveal that this enhancement stems from a combination of more compact crystal packing, driven by stronger intermolecular interactions, and a higher bond dissociation energy of the weakest C-NO2bond due to intramolecular stabilization. The superiority of this design principle was further validated as the energetic salts of TN-ANTA also consistently displayed higher densities and thermal stabilities than their corresponding isomers. This work establishes regioisomeric placement of functional groups as a powerful approach for the rational design of advanced energetic materials.
UR - https://www.scopus.com/pages/publications/105020448993
U2 - 10.1021/acs.orglett.5c03830
DO - 10.1021/acs.orglett.5c03830
M3 - Article
C2 - 41122883
AN - SCOPUS:105020448993
SN - 1523-7060
VL - 27
SP - 12081
EP - 12085
JO - Organic Letters
JF - Organic Letters
IS - 43
ER -