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The polymerization process that involves carbanion as an intermediate is called anionic polymerization. It is also a type of addition or chain-growth polymerization. Anionic polymerization gets initiated by a strong nucleophile such as an organolithium or a Grignard reagent. The most commonly used initiator for anionic polymerization is butyl lithium. Monomers involved in anionic polymerization must possess a vinyl group bonded to one or two electron-withdrawing groups. For instance,...
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The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the...
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The mechanism for anionic chain-growth polymerization involves initiation, propagation, and termination steps. In the initiation step, a nucleophilic anion, such as butyl lithium, initiates the polymerization process by attacking the π bond of the vinylic monomer. As a result, a carbanion, stabilized by the electron‐withdrawing group, is generated. The resulting carbanion acts as a Michael donor in the propagation step and attacks the second vinylic monomer, which acts as a Michael...
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The skeletal structure of polymers synthesized via radical polymerization is always branched. For example, the polymerization of ethylene by radical polymerization results in a low-density grade of polyethylene with a heavily branched skeletal structure. Here, the radical site abstracts hydrogen from the growing chain, and the radical site shifts from the end (a primary carbon center) to anywhere within the growing chain (a secondary carbon center). Consequently, the part of the chain from the...
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Self-Immolative RAFT-Polymer End Group Modification.

Maximilian Scherger1, Hans Joachim Räder1, Lutz Nuhn1

  • 1Max Planck Institute for Polymer Research, Ackermannweg 10, Mainz, 55128, Germany.

Macromolecular Rapid Communications
|February 25, 2021
PubMed
Summary
This summary is machine-generated.

This study introduces self-immolative reversible addition-fragmentation chain transfer (RAFT) polymer end group modifications. This novel method allows for the traceless release of amines and alcohols, expanding possibilities for stimuli-responsive polymer hybrids.

Keywords:
RAFT polymerizationbiodegradable polymersdisulfideend group modificationself-immolative linkers

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Area of Science:

  • Polymer Chemistry
  • Organic Synthesis
  • Bioconjugation Chemistry

Background:

  • Reversible modifications of RAFT-polymer end groups are typically limited to disulfide conjugates.
  • Self-immolative linkers offer traceless release of amines and alcohols via carbonates or carbamates.
  • Combining these strategies enables advanced polymer end group functionalization.

Purpose of the Study:

  • To introduce and demonstrate the concept of self-immolative RAFT-polymer end group modifications.
  • To create a versatile platform for reversible functionalization of polymer chain ends.
  • To explore applications in stimuli-responsive polymer hybrids and bioconjugation.

Main Methods:

  • Synthesis of model compounds (carbamates/carbonates) attached to disulfides.
  • One-pot reaction to attach these groups to RAFT-polymerized poly(N,N-dimethylacrylamide) end groups.
  • Characterization using 1H NMR, SEC, MS, diffusion ordered NMR, and TLC.
  • Expansion to protein-reactive carbonates for bioconjugation.

Main Results:

  • Quantitative end group modification of RAFT polymers was confirmed.
  • Reversible release of attached amines and alcohols under physiological reductive conditions was achieved.
  • Successful reversible bioconjugation of lysozyme and MMR nanobodies was demonstrated.
  • The self-immolative RAFT end group modification concept was validated.

Conclusions:

  • Self-immolative RAFT end group modifications provide a new basis for reversible functionalization.
  • This approach enables the introduction of diverse functionalities, including protein bioconjugates.
  • Opens novel opportunities for developing advanced stimuli-responsive polymer hybrids.