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A Methoxyamine‐Protecting Group for Organic Radical Battery Materials—An Alternative Approach
Author(s) -
Hansen KaiAnders,
Chambers Lewis C.,
Eing Matthias,
BarnerKowollik Christopher,
FairfullSmith Kathryn E.,
Blinco James P.
Publication year - 2020
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201903529
Subject(s) - chemistry , radical polymerization , chain transfer , reversible addition−fragmentation chain transfer polymerization , polymerization , moiety , radical initiator , polymer chemistry , combinatorial chemistry , methyl methacrylate , methacrylate , photochemistry , organic chemistry , polymer
Abstract 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 ( m CPBA) releases the electroactive PTMA. The redox activity of PTMA was confirmed by cyclic voltammetry in lithium‐ion coin cells.