Cocatalyst Binding Effects in Organocatalytic Ring-Opening Polymerization of l-Lactide,Macromolecules

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Cocatalyst Binding Effects in Organocatalytic Ring-Opening Polymerization of l-Lactide
Macromolecules ( IF 5.1 ) Pub Date : 2015-08-27 00:00:00 , DOI: 10.1021/acs.macromol.5b01140
Oleg I. Kazakov ₁ , Matthew K. Kiesewetter ₁

Affiliation

Thiourea/alkylamine cocatalysts have previously been shown to be effective systems for the ring-opening polymerization (ROP) of lactide, but an experimental explanation for the varied activity and selectivity of these structurally similar alkylamine cocatalysts combined with thiourea is elusive. In this work, several alkylamine bases are shown to be weakly associated with a thiourea cocatalyst in solution, and the nature of cocatalyst interactions vary with the identity of the alkylamine. Kinetic analyses of the organocatalytic ROP reactions reveal noninhibitory behavior in [alkylamine] and a new mode of activity for thiourea. Reactivity patterns are proposed based on computed cocatalyst geometries, and a new cocatalyst pair for the ROP of lactide is disclosed.

中文翻译：

丙交酯有机催化开环聚合中的助催化剂结合作用

硫脲/烷基胺助催化剂以前已被证明是丙交酯开环聚合（ROP）的有效体系，但是对这些结构相似的烷基胺助催化剂与硫脲结合使用的变化活性和选择性的实验解释却难以捉摸。在这项工作中，显示了几种烷基胺碱与溶液中的硫脲助催化剂弱结合，并且助催化剂相互作用的性质随烷基胺的身份而变化。动力学分析有机催化的ROP反应揭示了[烷基胺]中的非抑制行为和硫脲的新活性模式。根据计算出的助催化剂的几何构型提出了反应性模式，并公开了丙交酯的ROP的新的助催化剂对。

更新日期：2015-08-27

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