Backbone-Degradable Polymers via Radical Copolymerizations of Pentafluorophenyl Methacrylate with Cyclic Ketene Acetal: Pendant Modification and Efficient Degradation by Alternating-Rich Sequence,ACS Macro Letters

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Backbone-Degradable Polymers via Radical Copolymerizations of Pentafluorophenyl Methacrylate with Cyclic Ketene Acetal: Pendant Modification and Efficient Degradation by Alternating-Rich Sequence
ACS Macro Letters ( IF 5.1 ) Pub Date : 2021-09-23 , DOI: 10.1021/acsmacrolett.1c00513
Haiwang Lai ₁ , Makoto Ouchi ₁

Affiliation

This work deals with syntheses of backbone-degradable polymers via the radical copolymerization of pentafluorophenyl methacrylate (PFMA) with 5,6-benzo-2-methylene-1,3-dioxepane (BMDO), which undergoes ring-opening propagation to afford an ester-bonded backbone. The combination of the electron-deficient methacrylate with the electron-rich cyclic monomer allowed high crossover copolymerization, and the electronic effect was clarified by the comparison with the copolymerization of methyl methacrylate (MMA) and BMDO. The PFMA units of the resultant copolymer underwent quantitative alcoholysis or aminolysis transformation into methacrylate or methacrylamide units along with the pendant functionalization. The alternating-rich sequence was achieved by feeding an excess ratio of BMDO, which was supported by MALDI-TOF-MS of the copolymer obtained by the RAFT copolymerization. The methanolysis-transformed copolymer carrying MMA units was decomposed under basic condition, and the degradation efficiency was superior to that of the copolymer obtained via radical copolymerization of MMA with BMDO because of the alternating-rich sequence.

中文翻译：

甲基丙烯酸五氟苯酯与环状乙烯酮缩醛自由基共聚的主链可降解聚合物：通过交替富集序列进行侧链改性和高效降解

这项工作涉及通过甲基丙烯酸五氟苯酯 (PFMA) 与 5,6-苯并-2-亚甲基-1,3-二氧杂环己烷 (BMDO) 的自由基共聚合成主链可降解聚合物，该聚合物经过开环增长得到酯-键合骨干。缺电子甲基丙烯酸酯与富电子环状单体的组合允许高交叉共聚，并且通过与甲基丙烯酸甲酯（MMA）和BMDO的共聚的比较阐明了电子效应。所得共聚物的 PFMA 单元经历定量醇解或氨解转化为甲基丙烯酸酯或甲基丙烯酰胺单元以及侧基官能化。通过喂入过量比例的 BMDO 来实现交替富集序列，通过 RAFT 共聚得到的共聚物的 MALDI-TOF-MS 支持。甲醇解转化的带有MMA单元的共聚物在碱性条件下分解，由于交替富集序列，降解效率优于MMA与BMDO自由基共聚得到的共聚物。

更新日期：2021-10-19

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