Controlled Ring-Opening Polymerization of Macrocyclic Monomers Based on the Quinone Methide Elimination Cascade Reaction,Macromolecules

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Controlled Ring-Opening Polymerization of Macrocyclic Monomers Based on the Quinone Methide Elimination Cascade Reaction
Macromolecules ( IF 5.1 ) Pub Date : 2021-06-11 , DOI: 10.1021/acs.macromol.1c00872
Yuxiang He _{1,

2} , Ying Wu ₃ , Minghui Zhang _{1,

3} , Yuanxing Zhang _{1,

2} , Hao Ding _{1,

2} , Ke Zhang _{1,

2}

Affiliation

A controlled ring-opening polymerization (ROP) of macrocyclic monomers was developed based on the nucleophilic ring-opening mechanism for the first time. This novel ROP was designed to prepare backbone functional and sequence-defined polymers with controlled molecular weights and narrow dispersities (Đ < 1.1) by polymerizing the macrocycles with a quinone methide elimination-based self-immolative spacer as the “ring-opening trigger”. This ROP was initiated by an efficient nucleophilic substitution of activated carbonate with a primary amine to ring open the macrocyclic monomers. The following spontaneous 1,6-elimination-decarboxylation cascade reaction disassembled the self-immolative spacer to regenerate the primary amine end group for subsequent polymer chain propagation. The versatility of this novel ROP was demonstrated by the formation of well-defined water-soluble, backbone-degradable, and sequence-defined polyurethanes and their block copolymers.

中文翻译：

基于醌甲基化物消去级联反应的大环单体可控开环聚合

首次基于亲核开环机理开发了大环单体的受控开环聚合（ROP）。这种新型 ROP 旨在制备具有可控分子量和窄分散性 ( Đ< 1.1) 通过使用基于醌甲基化物消除的自焚间隔物作为“开环触发器”聚合大环。该 ROP 是通过用伯胺对活化碳酸酯进行有效的亲核取代以打开大环单体而引发的。以下自发的 1,6-消除-脱羧级联反应分解了自燃间隔基以再生伯胺端基，用于随后的聚合物链增长。这种新型 ROP 的多功能性通过形成明确定义的水溶性、骨架可降解和序列定义的聚氨酯及其嵌段共聚物来证明。

更新日期：2021-06-22

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