Fullerene Stabilizer 4,11,15,30-Tetraarylamino Fullerenoarylaziridine: Regioselective Synthesis, Crystallographic Characterization Derivatives, and Potential Application as Propellant Stabilizer

Abstract

The safe storage of propellants has become increasingly challenging because of extreme storage and operational environments. Hence, high-performance stabilizers should be urgently developed to improve the stability of propellants. In consideration of the stability mechanism of stabilizers and the excellent free radical scavenging ability of fullerenes, we synthesized six fullerene stabilizers, 4,11,15,30-tetraarylamino fullerenoarylaziridines, through the nucleophilic substitution reaction of hexachlorofullerene (C60Cl6) and corresponding aromatic amines with high yields. Their structures were adequately confirmed by HRMS, FT-IR, UV–vis, 1H NMR, 13C NMR spectroscopy, and single-crystal X-ray diffraction. The results of methyl violet test paper and thermogravimetric analysis manifested that the stabilities of these multifunctional fullerene derivatives to nitrocellulose were remarkably better than traditional stabilizers, such as N, N′-dimethyl-N, N′-diphenylurea and diphenylamine. Further electron paramagnetic resonance spectroscopy and FT-IR analysis reasonably revealed that this excellent stability ascribed the efficient scavenging ability for nitroxide radicals produced by nitrocellulose pyrolysis, thereby inhibiting the autocatalytic decomposition of nitrocellulose.