Improved Synthesis of Linear Poly(ethylenimine) via Low-Temperature Polymerization of 2-Isopropyl-2-oxazoline in Chlorobenzene,Macromolecules

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Improved Synthesis of Linear Poly(ethylenimine) via Low-Temperature Polymerization of 2-Isopropyl-2-oxazoline in Chlorobenzene
Macromolecules ( IF 5.1 ) Pub Date : 2015-05-14 00:00:00 , DOI: 10.1021/acs.macromol.5b00437
Bryn D. Monnery ₁ , Sunil Shaunak ₂ , Maya Thanou ₃ , Joachim H. G. Steinke

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Linear poly(ethylenimine) is a cationic polymer that is actively being progressed into clinical trials for gene therapy. The existing synthetic methodology produces a relatively broad distribution of molecular weights. We describe an improved method of polymerizing 2-alkyl-2-oxazolines as a route to linear poly(ethylenimine). By using an apolar noninterfering solvent (chlorobenzene) at low temperature (∼42 °C), the polymerization of 2-isopropyl-2-oxazoline proceeds much more rapidly than is observed in acetonitrile, and with far fewer side reactions. ¹H NMR observations showed close ion pairing at the propagating center (vice free ions in acetonitrile) to form a propagating complex of greater reactivity than free oxazolinium ions. Our results indicate that uniform or near uniform (“monodisperse”) polymers can be synthesized with nominal deviation from the theoretically achievable Poisson distributions.

中文翻译：

2-异丙基-2-恶唑啉在氯苯中的低温聚合改进了线性聚（乙烯亚胺）的合成

线性聚（乙烯亚胺）是一种阳离子聚合物，正在积极地进行基因治疗的临床试验。现有的合成方法产生相对较宽的分子量分布。我们描述了一种聚合2-烷基-2-恶唑啉作为线性聚（亚乙基亚胺）的途径的改进的方法。通过在低温（〜42°C）下使用非极性非干扰溶剂（氯苯），2-异丙基-2-恶唑啉的聚合反应比乙腈中观察到的反应快得多，并且副反应少得多。^1个1 H NMR观察表明，在传播中心离子紧密配对（乙腈中的自由离子），形成了比游离恶唑啉鎓离子具有更高反应性的传播络合物。我们的结果表明，可以在理论上与理论上可实现的泊松分布有名义偏差的情况下，合成均匀或接近均匀的（“单分散”）聚合物。

更新日期：2015-05-14

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