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Polynitro‐Functionalized Dipyrazolo‐1,3,5‐triazinanes: Energetic Polycyclization toward High Density and Excellent Molecular Stability
Author(s) -
Yin Ping,
Zhang Jiaheng,
Imler Gregory H.,
Parrish Damon A.,
Shreeve Jean'ne M.
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201704687
Subject(s) - thermal stability , chemistry , crystal (programming language) , tricyclic , stereochemistry , organic chemistry , computer science , programming language
A new fused N‐heterocyclic framework, dipyrazolo‐1,3,5‐triazinane, was synthesized and the physiochemical properties of its derivatives were investigated to evaluate the integrated energetic performance. In contrast to 1,3,5‐trinitro‐1,3,5‐triazinane (RDX) featuring a distorted chair confirmation, polynitro‐functionalized dipyrazolo‐1,3,5‐triazinanes have nearly planar backbones, thereby enhancing the density and thermal stability. Among these new energetic tricyclic compounds, 5 a and 12 show favorable crystal densities of 1.937 g cm −3 and 1.990 g cm −3 at 150 K, respectively, which rank highest in triazinane‐based energetic compounds. Additionally, this synthetic approach was carried out to form seven‐membered and eight‐membered rings, giving rise to tetranitro dipyrazolo‐1,3,5‐triazepane ( 5 b ) and tetranitro dipyrazolo‐1,3,5‐triazocane ( 5 c ), respectively.