A series of aziridino[60]fullerenes was synthesized by the reaction of octabromo[60]fullerene with various anilines. Their ability to absorb free radicals and acid gases was studied, and their potential applications as stabilizers in nitrocellulose-containing propellants were discussed. The structure of aziridino[60]fullerenes was characterized by X-ray single-crystal diffraction, NMR, HRMS, FT-IR, and UV-vis. The compatibilities of aziridino[60]fullerenes with nitrocellulose and their stabilization effect on nitrocellulose were evaluated by methyl violet, differential thermal analysis, isothermal weight loss, and vacuum stability test methods. The results reveal that aziridino[60]fullerenes have more excellent compatibility and stability than the traditional stabilizers DPA and C2. Moreover, their stabilization mechanism was studied by electron spin resonance spectroscopy. The results show that aziridino[60]fullerenes could effectively eliminate the nitrogen oxides released by nitrocellulose autocatalysis, and they could be used as a new stabilizer for nitrocellulose-containing propellants.

The stereoselective preparation of fullerene bis-adducts through nontethered methods remains difficult due to the significant amount of regioisomers produced. The trans-4 aziridino[60]fullerenes, C60(NC6H4R)n (n = 1 or 2, R = OMe, OEt, OBu), were selectively synthesized even without a catalyst by reacting octabromofullerene with the corresponding aniline. Nuclear magnetic resonance spectroscopy, UV-vis spectroscopy, and X-ray structural analysis provided convincing characterization of the compounds. A possible reaction process was proposed to clarify the synthesis of highly regioselective trans-4-bisaziridino[60]fullerenes. The possible use of these aziridino[60]fullerene derivatives as propellant stabilizers was also explored.

Comprehensive SummaryThe stereoselective preparation of fullerene bis‐adducts through nontethered methods remains difficult due to the significant amount of regioisomers produced. The trans‐4 aziridino[60]fullerenes, C60(NC6H4R)n (n = 1 or 2, R = OMe, OEt, OBu), were selectively synthesized even without a catalyst by reacting octabromofullerene with the corresponding aniline. Nuclear magnetic resonance spectroscopy, UV‐vis spectroscopy, and X‐ray structural analysis provided convincing characterization of the compounds. A possible reaction process was proposed to clarify the synthesis of highly regioselective trans‐4‐bisaziridino[60]fullerenes. The possible application of these aziridino[60]fullerene derivatives as propellant stabilizers was also explored.