A new design strategy for constructing powerful cage energetic compounds
with low sensitivity: the combination of a nitrogen-rich cage, nitro
groups and amino groups based on a one-step reaction with the perfect
atomic efficiency
Abstract
In the present study, a novel strategy for constructing new cage
energetic compounds with both high energy and low sensitivity was
proposed. That is to use a 3D nitrogen-rich cage compounds as the core
parent molecule to set the basis for obtaining high energy, and followed
by the introduction of a moderate number of nitro groups into the cage
which be linked with the carbon atoms to further improve the energy
without increasing the sensitivity obviously, and controlling the
reaction difficulty caused by the too many nitro groups as low as
possible. The amino groups were introduced into the structure also to
adjust the balance of energy and sensitivity. Finally, more importantly,
the formation of nitrogen-rich cage, and the introduction of nitro/amino
groups were achieved synchronously by a typical and attractive one-step
reaction (The Diels-Alder reaction) which possesses the 100% atomic
efficiency. Based on this strategy, six series of amino-substituted
nitrogen-rich azoles were used as the dienes, to react with different
dienophiles like the tetranitroethylene (TNE) to form the final cage
products. From the theoretical investigation results, five optimal
compounds (PA0, PB0, PC0, PE0, PE1) with low reaction energy barrier
(11.2 to 31.6 kcal/mol), and may set the high energy of CL-20 and low
sensitivity of TNT together, have been screened out as new advanced
energetic compounds successfully. This study may provide a new feasible
strategy and a unique perspective for developing new advanced energetic
compounds.