A Methoxyamine-Protecting Group for Organic Radical Battery Materials-An Alternative Approach.,ChemSusChem

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A Methoxyamine-Protecting Group for Organic Radical Battery Materials-An Alternative Approach.
ChemSusChem ( IF 7.5 ) Pub Date : 2020-04-15 , DOI: 10.1002/cssc.201903529
Kai-Anders Hansen ₁ , Lewis C Chambers ₁ , Matthias Eing _{1,

2} , Christopher Barner-Kowollik ₁ , Kathryn E Fairfull-Smith ₁ , James P Blinco ₁

Affiliation

An alternative synthetic route towards the widely employed electroactive poly(TEMPO methacrylate) (PTMA) via a thermally robust methoxyamine-protecting group is demonstrated herein. Protection of the radical moiety of hydroxy-TEMPO with a methyl functionality and subsequent esterification with methacrylic anhydride allows the high-yielding formation of the novel monomer methyl-TEMPO methacrylate (MTMA). The polymerization of MTMA to poly(MTMA) (PMTMA) is investigated via free radical polymerization and reversible addition-fragmentation chain-transfer polymerization (RAFT), a reversible-deactivation radical polymerization technique. Cleavage of the temperature-stable methoxyamine functionality by oxidative treatment of PMTMA with meta-chloroperbenzoic acid (mCPBA) releases the electroactive PTMA. The redox activity of PTMA was confirmed by cyclic voltammetry in lithium-ion coin cells.

中文翻译：

有机自由基电池材料的甲氧基胺保护基团-一种替代方法。

本文展示了通过耐热的甲氧基胺保护基团向广泛使用的电活性聚甲基丙烯酸TEMPO（PTMA）的另一种合成途径。用甲基官能团保护羟基-TEMPO的自由基部分，然后用甲基丙烯酸酐进行酯化，可以高产率地形成新型单体甲基-TEMPO甲基丙烯酸甲酯（MTMA）。通过自由基聚合和可逆加成-断裂链转移聚合（RAFT）（可逆失活自由基聚合技术）研究了MTMA聚合为聚（MTMA）（PMTMA）。通过用间氯过苯甲酸（mCPBA）氧化处理PMTMA来裂解温度稳定的甲氧基胺官能团，从而释放出电活性PTMA。

更新日期：2020-04-15

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