Aziridine-derived poly(sulfonamide thioether)s: Synthesis and the self-healing elastomeric properties

Abstract

We introduce a straightforward polymerization methodology for synthesizing poly(sulfonamide thioether)s by the step-growth polyaddition of dithiols to chiral bis(2-monosubstituted N-sulfonyl aziridine)s. Undesired cross-linking reactions do not occur when employing the nucleophilic catalyst tributylphosphine. The resulting polymers exhibit both optical activity and impressive thermal stability, with a decomposition temperature (Td,5%) up to 328.1 °C. Moreover, one of the synthesized polymers, incorporating the diethylene glycol unit, demonstrates remarkable mechanical properties, presenting a tensile strength exceeding 2.0 MPa and an extraordinary strain tensile rate exceeding 2,000%. Most notably, this elastomer exhibits rapid self-healing capabilities at room temperature without external stimuli. These findings not only contribute to the synthetic methods for aziridine-derived polymeric materials but also offer promising avenues for developing advanced elastomers with exceptional mechanical and self-healing attributes.