Fully-iodinated bridged pyrroles as high thermostable energetic biocidal materials

Pyrrole is one of the important versatile skeletons for functional materials, fully-substituted pyrroles can achieve multiple substitutions. But, spatial site resistance effects make its synthesis difficult. In this work, a series of fully-iodinated bridged pyrroles (compounds 8-13 ) as energetic biocidal compounds were synthesized through two-step. They show high iodine content of 82.98% -88.02%, and high thermal stability ( T d : 267∼344 °C) which is a significantly improved compared to 2,3,4,5-tetraiodo-1H-pyrrole (TIPL, T d : 168 °C). Furthermore, good detonation pressure ( p ) and detonation velocity ( D ) were realized, showing great prospective for applications as potential energetic biocidal materials. This study has investigated a simple and mild two-step synthetic methods for fully-iodinated pyrole compounds, within high iodine content and high stability, showing great potentiality for energetic biocidal materials. • An efficient synthesis of fully iodinated pyrroles energetic biocidal compounds was developed. • All newly synthesized compounds ( 8-13 ) demonstrate high iodine content (82.98-88.02 %) and excellent themal stability ( T d : 267-344 °C). • Alkyl bridging strategy significantly solves the problem of poor thermal stability of TIPL ( T d : 168 °C)