Expanding the Limits of Organic Energetic Materials: High-Performance Alliance of 1,3,4-Thiadiazole and Furazan Scaffolds

Expanding the Limits of Organic Energetic Materials: High-Performance Alliance of 1,3,4-Thiadiazole and Furazan Scaffolds Full article

Journal

Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263

Output data

Year: 2024, Volume: 89, Number: 1, Pages: 174-182 Pages count : 9 DOI: 10.1021/acs.joc.3c01858

Authors

Deltsov Ilya D. ¹ , Ananyev Ivan V. ² , Meerov Dmitry B. ³ , Fershtat Leonid L. ^1,4

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, Moscow 119991, Russian Federation
2	N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, GSP-1, Leninsky Prospect, 31, Moscow 119991, Russian Federation
3	N. N. Semenov Federal Research Centre for Chemical Physics, Russian Academy of Sciences, 4 Kosygin Strasse, Moscow 119991, Russian Federation
4	National Research University Higher School of Economics, Myasnitskaya strasse, 20, Moscow 101000, Russian Federation

A majority of known and newly synthesized energetic materials comprise polynitrogen or nitrogen–oxygen heterocycles with various explosophores. However, available structural combinations of these organic scaffolds are finite and are about to reach their limits. Herein, we present the design and synthesis of a series of sulfur-containing polyazole structures comprising 1,3,4-thiadiazole and furazan rings linked by C–C bonds and enriched with energetic nitro and azo functionalities. In terms of detonation performance, all synthesized 1,3,4-thiadiazole-furazan assemblies (D = 7.7–7.9 km s–1; P = 26–28 GPa) lie between the powerful explosive TATB (D = 8.0 km s–1; P = 31 GPa) and melt-cast material TNT (D = 6.9 km s–1; P = 23 GPa). In the synthesized series, azo-bridged derivative 5 seems to be most practically interesting, as it combines a relatively high energetic performance (D = 7.9 km s–1; P = 28 GPa), a very high thermal stability (271 °C), and insensitivity to friction. By these functional properties, 5 outperforms the benchmark heat-resistant explosive hexanitrostilbene (HNS). To the best of our knowledge, this is the first example of an energetic alliance of furazan and 1,3,4-thiadiazole scaffolds and a rare case of sulfur-containing high-energy materials, which can certainly be considered as an evolutionary step in energetic materials science.

Deltsov I.D. , Ananyev I.V. , Meerov D.B. , Fershtat L.L.
Expanding the Limits of Organic Energetic Materials: High-Performance Alliance of 1,3,4-Thiadiazole and Furazan Scaffolds
Journal of Organic Chemistry. 2024. V.89. N1. P.174-182. DOI: 10.1021/acs.joc.3c01858 WOS Scopus OpenAlex

Web of science:	WOS:001137583600001
Scopus:	2-s2.0-85180067114
OpenAlex:	W4389537991

DB	Citing
OpenAlex	26
Scopus	27
Web of science	25