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Cationic Chain-Growth Polymerization: Mechanism00:57

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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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Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
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Anionic Chain-Growth Polymerization: Mechanism01:04

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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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Anionic Chain-Growth Polymerization: Overview01:20

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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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Olefin Metathesis Polymerization: Overview01:13

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Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
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Polymer Classification: Stereospecificity01:26

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Polymerization generates chiral centers along the entire backbone of a polymer chain. Accordingly, the stereochemistry of the substituent group has a significant effect on polymer properties. Polymers formed from monosubstituted alkene monomers feature chiral carbons at every alternate position in the polymer backbone. Relative to the predominant orientation of substituents at the adjacent chiral carbons, the polymer can exist in three different configurations: isotactic, syndiotactic, and...
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Dual Self-Promoted Ring-Opening Polymerization towards Cationic Polypeptoids with Stable Helices.

Kunyu Gan1, Ronald N Zuckermann2, Ning Zhao3,4

  • 1State and Local Joint Engineering Laboratory for Novel Functional Polymeric Materials, Jiangsu Key Laboratory of Advanced Functional Polymer Design and Application, Suzhou Key Laboratory of Macromolecular Design and Precision Synthesis, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, 215123, China.

Angewandte Chemie (International Ed. in English)
|November 11, 2025
PubMed
Summary
This summary is machine-generated.

Researchers developed stable helical cationic polypeptoids using bulky side chains. These novel polymers show reduced cytotoxicity and faster cellular uptake than traditional poly(l-lysine), offering promise for biological applications.

Keywords:
Cationic helicesControlled ring‐opening polymerizationPeptidomimetic polymersPolypeptoidsSelf‐promoted polymerization

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Area of Science:

  • Polymer Chemistry
  • Biomaterials Science
  • Organic Synthesis

Background:

  • Cationic polymers, like polypeptides with lysine, are vital in biology but often have unstable helices due to side-chain repulsion.
  • Developing stable cationic helical structures is a significant challenge in polymer design.

Purpose of the Study:

  • To synthesize novel, stable helical cationic polypeptoids with bulky tertiary amine side chains.
  • To investigate the mechanism of their formation and helix stabilization.
  • To evaluate their potential for biological applications by comparing them to conventional cationic polypeptides.

Main Methods:

  • Controlled ring-opening polymerization of cyclic monomers with bulky, chiral tertiary amine side chains.
  • Incorporation of achiral backbones to induce stable helical structures.
  • Quaternization to create cationic polypeptoids.
  • Characterization of helical stability and comparison of cytotoxicity and cellular uptake kinetics with poly(l-lysine).

Main Results:

  • Successfully synthesized structurally diverse polyproline-I-like helical cationic polypeptoids.
  • Demonstrated remarkable helix stability, contrasting with conventional cationic polypeptides.
  • Identified C─H···O hydrogen bonding and steric hindrance as key stabilization mechanisms.
  • Observed significantly lower cytotoxicity and faster cellular uptake compared to poly(l-lysine).

Conclusions:

  • Bulky tertiary amine side chains in polypeptoids can induce and stabilize helical structures.
  • These cationic helical polypeptoids offer a promising platform for biomaterials due to their stability, low cytotoxicity, and efficient cellular uptake.
  • The findings provide new strategies for designing advanced functional polymers for biological applications.