2,4,5‐Trinitroimidazole‐Based Energetic Salts

Abstract

Hetero Diels‐Alder (HDA) cycloaddition – as an effective modular conjugation approach – is employed to graft thioamide endfunctional oligopeptides onto solid cyclopentadienyl (Cp) functional cellulose substrates generating cellulose‐peptide hybrid materials. The highly reactive Cp moieties serve as diene functionality in the consecutive HDA reaction on the biosubstrate surface. Oligopeptides (i.e., the model peptide Gly‐Gly‐Arg‐Phe‐Pro‐Trp‐Trp‐Gly and the antimicrobial peptide tritrpticin) are functionalized at their N‐termini employing strongly electron deficient thiocarbonyl thio compounds resulting in biomacromolecules bearing a thioamide endgroup. The dienophile‐ functional peptides readily undergo HDA reactions at ambient temperature and under mild conditions in solution with synthetic polymers as well as on solid (bio)substrates. An in‐depth investigation is provided of the influence of the temperature, the Lewis acid catalysis and the side group exchange of thioamide functional oligopeptides reacting with Cp terminated poly(methyl methacrylate) (Mn = 2100 g·mol−1, PDI = 1.1) in homogenous solution as well as Cp functionalized cellulose in a heterogeneous system. To assess the success of the grafting reaction, the soluble samples were subjected to characterization methods such as size exclusion chromatography (SEC) and SEC‐electrospray ionization mass spectrometry (SEC‐ESI‐MS). The heterogeneous “grafting‐to” reactions were monitored using high resolution attenuated total reflection (ATR) Fourier transform infrared microscopy (HR‐FTIRM) imaging, X‐ray photoelectron spectroscopy (XPS) and elemental analysis. Evaluation via elemental analysis leads to quantitative peptide cellulose surface loading capacities.

4‐Nitro‐3‐(5‐tetrazole)furoxan and Its Salts: Synthesis, Characterization, and Energetic Properties

“…Nevertheless, its barium salt has good solubility in water. Thus, energetic salts 5-9 were readily synthesized by metathesis reactions of BaA C H T U N G T R E N N U N G (TNF) 2 formed in situ with one equivalent of the corresponding sulfate salt (Scheme 1). All of the prepared energetic salts proved to be stable in air and could be stored for extended periods.…”

Energetic Nitrogen Rich Salts of N,N‐bis[1(2)H‐Tetrazol‐5‐yl]amine

“…[7] Since some organic anions have considerable nitrogen content and are expected to have attractive stabilities toward friction, impact, and heat, they are also good candidates for energetic salt design, e.g., 5,5′-azotetrazolate, [8] 3,5-dinitro-1,2,4-triazolate, [9] 4,5-dinitroimidazolate, [9] 3-nitro-triazolate, [10] 5-nitro-tetrazolate, [10,11] iminobis(5-tetrazolate), [8c] 5′-bis(tetrazolate), [8c] bisdinitroimidazolate, [12] 3-nitro-1,2,4-triazol-5-one, [13] picrate, [14] 3-amino-6-nitroamino-tetrazine anion, [15] and trinitroimidazole. [16] Recently, copper complexes of N,N-bis-(1 (2)H-tetrazol-5-yl)amine (H 2 Bta) (1) were reported. [17] The acidic protons of H 2 Bta enable the formation of the corresponding salts by reactions with nitrogen-rich bases.…”

Synthesis, Structure, and Characterization of 3, 4′‐Bis‐1H‐1, 2,4‐triazolium Picrate Salt: A New High‐Energy Density Material

“…Besides, materials comprising structure of azole rings always show a better oxygen balance property in plenty of practical test. [14,[16][17][18][19] Among most of the energetic compounds, 1,2,4-triazole and its derivatives are very promising because of both theoretical and practical prospect. Shreeve, Klapötke, and others researchers have found that they have good physical and chemical performances, as well as excellent environmental compatibility, compared to other compounds.…”