Photochemical Strategies Enable the Synthesis of Tunable Azetidine-Based Energetic Materials

Despite their favorable properties, azetidines are often overlooked as lead compounds across multiple industries. This is often attributed to the challenging synthesis of densely functionalized azetidines in an efficient manner. In this work, we report the scalable synthesis and characterization of seven azetidines with varying regio-and stereochemistry and their application as novel azetidine-based energetic materials, enabled by the visible-light-mediated aza Paterno-Buchi reaction. The performance and stark differences in the physical properties of these new compounds make them excellent potential candidates as novel solid melt-castable explosive materials, as well as potential liquid propellant plasticizers. This work highlights the scalability and utility of the visible-light aza Paterno-Buchi reaction and demonstrates the impact of stereochemical considerations on the physical properties of azetidine-based energetics. Considering the versatility and efficiency of the presented synthetic strategies, we expect that this work will guide the development of new azetidine-based materials in the energetics space as well as other industries.

Automated summary

In this work, a scalable synthesis method for various azetidine compounds with different properties was developed, and their potential applications in the field of high-energy materials were explored. The synthesized compounds, prepared through a visible-light-mediated reaction, exhibited excellent performance and physical properties, making them promising candidates for novel solid melt-castable explosive materials and liquid propellant plasticizers. This study demonstrates the feasibility of the visible-light synthesis method and highlights the influence of stereochemistry on the physical properties of azetidine-based energetics.