Radical Ring-Opening Copolymerization of Cyclic Ketene Acetals and Maleimides Affords Homogeneous Incorporation of Degradable Units,ACS Macro Letters

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Radical Ring-Opening Copolymerization of Cyclic Ketene Acetals and Maleimides Affords Homogeneous Incorporation of Degradable Units
ACS Macro Letters ( IF 5.1 ) Pub Date : 2017-09-15 00:00:00 , DOI: 10.1021/acsmacrolett.7b00572
Megan R Hill _{1,

2} , Elise Guégain ₂ , Johanna Tran ₂ , C Adrian Figg ₁ , Andrew C Turner ₁ , Julien Nicolas ₂ , Brent S Sumerlin ₁

Affiliation

Radical copolymerization of donor–acceptor (D-A) monomer pairs has served as a versatile platform for the development of alternating copolymers. However, due to the use of conventional radical polymerization, the resulting copolymers have generally been limited to nondegradable vinyl polymers. By combining radical D-A copolymerization with radical ring-opening polymerization (rROP), we have synthesized an alternating copolymer with a high incorporation of degradable backbone units. Copolymerization of N-ethyl maleimide (NEtMI) with the cyclic ketene acetal (CKA) 2-methylene-4-phenyl-1,3-dioxolane (MPDL) was demonstrated to proceed in an alternating fashion, and controlled polymerization was achieved using reversible addition–fragmentation chain transfer (RAFT) polymerization. Spontaneous copolymerization, in the absence of an exogenous initiating source, occurred when the mixture of monomers was heated, presumably due to the large electron disparity between the comonomers. Chain-extension with styrene afforded well-defined P(MPDL-alt-NEtMI)-b-polystyrene copolymers, and degradation of the homopolymers and block copolymers showed complete breakdown of the alternating copolymer.

中文翻译：

环状乙烯酮缩醛和马来酰亚胺的自由基开环共聚可均匀掺入可降解单元

供体-受体 (DA) 单体对的自由基共聚已成为开发交替共聚物的通用平台。然而，由于使用传统的自由基聚合，所得共聚物通常仅限于不可降解的乙烯基聚合物。通过将自由基 DA 共聚与自由基开环聚合 (rROP) 相结合，我们合成了一种具有高掺入可降解骨架单元的交替共聚物。N的共聚-乙基马来酰亚胺 (NEtMI) 与环状乙烯酮缩醛 (CKA) 2-亚甲基-4-苯基-1,3-二氧戊环 (MPDL) 被证明以交替方式进行，并使用可逆加成-断裂链实现受控聚合转移（RAFT）聚合。在没有外源引发源的情况下，当加热单体混合物时会发生自发共聚，这可能是由于共聚单体之间的电子差异很大。用苯乙烯扩链提供了定义明确的 P(MPDL- alt - NEtMI) -b-聚苯乙烯共聚物，均聚物和嵌段共聚物的降解表明交替共聚物完全分解。

更新日期：2017-09-15

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