Aziridine in Polymer Science: Unconventional Cycloaddition and Migration in Mechanochemically Responsive Polymers
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초록
내용
Last decades have witnessed success of epoxide for a synthon in small molecule synthesis and polymeric applications. Whereas the neighbor N-heterocycle, aziridine, has demonstrated its potential to overcome problems that epoxide encounters in organic synthesis, it has not successfully debuted yet in polymer science and technology. This presentation describes synthesis and characterization of polymers containing aziridine mechanophores and mechanochemical reactions of the polymers. Ring opening metathesis copolymerization with cyclooctene and the aziridine containing macrocyclic monomer affords aziridine containing polymers. Ultrasound-driven pulling force along the polymer backbone triggers chemical reactions at the aziridine mechanophores. Force-induced activation of aziridine i) steers cycloaddition of aziridine toward routes that are inaccessible under traditional thermal and photochemical conditions and ii) permits access to site-selective degradation via N-substituent migration.