Energetic N-Nitramino/N-Oxyl-Functionalized Pyrazoles with Versatile π–π Stacking: Structure–Property Relationships of High-Performance Energetic Materials

N-Nitramino/N-oxyl functionalization strategies were employed to investigate structure–property relationships of energetic materials. Based on single-crystal diffraction data, π–π stacking of pyrazole backbones can be tailored effectively by energetic functionalities, thereby resulting in diversified energetic compounds. Among them, hydroxylammonium 4-amino-3,5-dinitro-1H-pyrazol-1-olate and dipotassium N,N′-(3,5-dinitro-1H-pyrazol-1,4-diyl)dinitramidate, with unique face-to-face π–π stacking, can be potentially used as a high-performance explosive and an energetic oxidizer, respectively.