Alternating Terpolymers through Cyclopolymerization and Subsequent Orthogonal Functionalization

A method for the synthesis of functionalized alternating copolymers by reversible deactivation radical polymerization was developed. Copolymerization by reversible addition–fragmentation chain transfer of hexenyl vinyl ether with a novel fluorinated divinyl monomer yields alternating cyclopolymers t...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2022-09, Vol.61 (39), p.e202206964-n/a
Main Authors: Gerdt, Philipp, Studer, Armido
Format: Article
Language:English
Subjects:
Acylation
Alternating Polymerization
Chain transfer
Chemical reactions
Chemical synthesis
Copolymerization
Copolymers
Deactivation
Orthogonal Functionalization
Polymerization
Polymers
Postmodification
Radical Polymerization
RAFT Polymerization
Sulfhydryl Compounds
Terpolymers
Transesterification
Vinyl ethers
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Summary:A method for the synthesis of functionalized alternating copolymers by reversible deactivation radical polymerization was developed. Copolymerization by reversible addition–fragmentation chain transfer of hexenyl vinyl ether with a novel fluorinated divinyl monomer yields alternating cyclopolymers that can be chemoselectively modified by three distinct orthogonal functionalization reactions. Along the thiol‐ene click reaction and amidation, a third functionalization was achieved via NHC‐catalyzed transesterification or acylation resulting in a small library of ABC‐type alternating terpolymers. The alternating radical copolymerization of divinyl monomer A and hex‐5‐enyl vinyl ether (HVE) using reversible addition–fragmentation chain transfer (RAFT) is reported. The obtained cyclopolymer B can chemically be further modified by three orthogonal functionalization reactions i.e. thiol‐ene click reaction, amidation and transesterification or acylation to provide access to various alternating ABC‐type terpolymers C.
ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.202206964