Exploring the effects of inserting heteroatoms (N, O, S) into 9-heterocyclo[3.3.1]nonane frameworks on the properties of their energetic derivatives

Bicyclo[3.3.1]nonane scaffold is a privileged ring system frequently encountered in a variety of cage-like compounds. Exploring the synthesis of bicyclo[3.3.1]nonane is of great significance for the design and application of cage-like energetic compounds. In this paper, four novel energetic compounds with a bicyclo[3.3.1]nonane skeleton containing three types of heteroatoms (N, O, S) were synthesized with excellent yields via simple and facile synthetic routes from 1,5-cyclooctadiene. Moreover, these compounds have higher density and lower sensitivity than classical high explosive TNT. The predictions of detonation performance indicate that the as-prepared energetic compounds containing nitrogen and oxygen heteroatoms exhibit better detonation velocity and pressure ( D > 7500 m·s -1 , p > 26 GPa) than TNT. Furthermore, detonation experiments were conducted to evaluate the impact of incorporating heteroatoms (N, O, S) on detonation performance. Therefore, the inserting of heteroatoms such as N, O and S into the bicyclo[3.3.1]nonane skeleton significantly affects density and detonation performance of its derivatives, which provide theoretical guidance for the design and synthesis of adamantane-based energetic material frameworks and facilitate the advancement of cage-like energetic materials. Seven energetic compounds with bicyclo[3.3.1]nonane skeleton containing three types of heteroatoms (N, O, S) were synthesized and their single crystal structures, thermal stabilities and detonation performances were intensive discussed to show light on the effect of skeletal editing of framework of energetic compounds. • The bicyclo[3.3.1]nonane frameworks is an important intermediate for the synthesis of polynitroadamantane. Inserting heteroatoms (N, O, S) into the bicyclo[3.3.1]nonane structure, providing theoretical support for the design and synthesis of novel high-energy density compounds. • Seven energetic compounds with bicyclo[3.3.1]nonane skeleton containing three types of heteroatoms (N, O, S) were synthesized and their single crystal structures, thermal stabilities and detonation performances were intensive discussed to show light on the effect of skeletal editing of framework of energetic compounds. • The inserting of heteroatoms such as N, O and S into the bicyclo[3.3.1]nonane skeleton significantly affects density, stability and detonation performance of its derivatives, which provide theoretical guidance for the design and synthesis of cage-like energetic materials. • Abstract Graphics