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N ‐Diazo‐Bridged Nitroazoles: Catenated Nitrogen‐Atom Chains Compatible with Nitro Functionalities
Author(s) -
Yin Ping,
Parrish Damon A.,
Shreeve Jean'ne M.
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201402762
Subject(s) - diazo , nitro , oxygen balance , detonation , nitrogen , chemistry , nitrogen atom , atom (system on chip) , thermal stability , oxygen , computational chemistry , photochemistry , group (periodic table) , organic chemistry , explosive material , alkyl , computer science , embedded system
N ‐diazo‐bridged azoles were synthesized based on oxidative coupling of N ‐aminoazoles. Incorporation of extended catenated nitrogen‐atom chains with nitro groups led to compounds with favorable functional compatibilities. This combination gives rise to a series of high‐density energetic materials (HEDMs) with high heats of formation, enhanced densities, positive oxygen balances, and good detonation properties while retaining excellent thermal stabilities and relatively low impact sensitivities. Calculated and experimental studies showed the delicate balance between the length of the nitrogen atom chain, energetic performance, and inherent stability, thus, providing a promising strategy for designing advanced energetic materials.