Synthesis and Reactivity of Diazirine-Containing Polymers via Controlled Radical Polymerization
Banruo Huang, Mizhi Xu, Craig J. Hawker
Abstract
High Resolution Image Download MS PowerPoint Slide The synthesis and application of multifunctional diazirines as efficient precursors for the on-demand generation of carbenes is demonstrated. While small-molecule multifunctional diazirines have seen significant application in fields such as plastic compatibilization and photopatterning, the synthesis and polymerization of diazirine-based monomers is unexplored. This study focuses on the preparation of diazirine-containing polyacrylates and polymethacrylates through controlled radical polymerization. Both reversible addition–fragmentation chain-transfer (RAFT) polymerization and atom-transfer radical polymerization (ATRP) techniques are shown to be efficient for preparing polymers with targeted diazirine contents and degrees of polymerization. The resulting polymers represent a versatile cross-linking platform through reaction with ubiquitous C–H bonds. This stability and synthetic accessibility underscore the potential of diazirine-containing polymers for efficient cross-linking and functionalization strategies.