Dewar Heterocycles as Versatile Monomers for Ring-Opening Metathesis Polymerization,ACS Macro Letters

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Dewar Heterocycles as Versatile Monomers for Ring-Opening Metathesis Polymerization
ACS Macro Letters ( IF 5.1 ) Pub Date : 2020-05-01 , DOI: 10.1021/acsmacrolett.0c00227
Sepand K Nistanaki ₁ , Hosea M Nelson ₁

Affiliation

We report the utility of readily available heterocycles as precursors to unique ring-opening metathesis polymerization (ROMP) monomers. Photochemical valence isomerization reactions of pyridones, dihydropyridines, and pyrones dearomatize the parent heterocycles to their highly strained Dewar isomers, which readily engage in controlled ROMP reactions using Grubbs catalysts. This strategy is used to access polymer backbones that contain strained β-lactam and azetidine cores, which can be further derivatized using postpolymerization chemistries. We demonstrate this through the synthesis of water-soluble β-amino acid polymers that have potential applications as biomedical materials, along with the synthesis of highly soluble poly(acetylene) derivatives, which have potential applications as organic conductive materials derived from biofeedstock chemicals.

中文翻译：

杜瓦杂环化合物作为开环易位聚合的通用单体。

我们报告了容易获得的杂环作为独特的开环复分解聚合（ROMP）单体的前体的效用。吡啶酮，二氢吡啶和吡喃酮的光化学价异构化反应使母体杂环芳构化为高度应变的杜瓦异构体，使用Grubbs催化剂可轻松进行受控的ROMP反应。此策略用于访问包含应变的β-内酰胺和氮杂环丁烷核的聚合物主链，可以使用后聚合化学方法对其进行进一步衍生。我们通过合成具有潜在用途的生物医学材料水溶性β-氨基酸聚合物，以及合成高可溶性聚乙炔衍生物，证明了这一点，

更新日期：2020-05-01

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