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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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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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The attack of a nucleophile at the β carbon of an α,β-unsaturated carbonyl compound is called conjugate addition. Conjugate addition reactions of active methylene compounds, such as β-diketones, β-keto esters, β-keto nitriles, and α-nitro ketones, are called Michael addition reactions.
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Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
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Chain-growth or addition polymerization is successive addition reactions of monomers with a polymer chain. In radical chain-growth polymerization, the reaction proceeds via a free-radical intermediate. The free radical is formed from radical initiators, which spontaneously generate free radicals by homolytic fission. Organic peroxides (such as dibenzoyl peroxide, as shown in Figure 1) or azo compounds are popular radical initiators. A low concentration ratio of radical initiator to monomer is...
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Aza-Michael Addition-Fragmentation Ring-Opening Polymerization.

Dan Huang1,2, Zhen Zhu2, Derong Cao1

  • 1School of Chemistry and Chemical Engineering, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou 510640, China.

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|May 20, 2025
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Summary
This summary is machine-generated.

This study introduces a new ring-opening polymerization method that breaks C(sp3)-N bonds in cyclic monomers under ambient conditions. The novel approach yields functional polyamines with controlled properties and unexpected cis-stereoselectivity.

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Area of Science:

  • Polymer Chemistry
  • Organic Synthesis
  • Materials Science

Background:

  • Cleaving carbon-nitrogen (C(sp3)-N) bonds in unstrained cyclic monomers for ring-opening polymerization (ROP) is a significant challenge.
  • Existing methods often require harsh conditions or are limited to strained monomers.

Purpose of the Study:

  • To develop a novel strategy for cleaving C(sp3)-N bonds in less-strained cyclic monomers.
  • To achieve controlled ring-opening polymerization yielding functional polyamines.
  • To investigate the stereochemical outcome and mechanism of the polymerization.

Main Methods:

  • Integration of cascade aza-Michael/retro-aza Michael reaction with a chain-growth polymerization mechanism.
  • Utilizing less-strained cyclic monomers under ambient conditions.
  • Density functional theory (DFT) calculations to elucidate stereoselectivity.

Main Results:

  • Successful cleavage of C(sp3)-N bonds in unstrained cyclic monomers.
  • Synthesis of cinnamate-containing polyamines with controlled molecular weight and narrow dispersity.
  • Demonstration of unexpected cis-stereoselectivity in the polymerization.
  • Evidence of excellent polymerization control, including linear molecular weight increase with conversion and high chain-end fidelity.
  • Versatile application shown through copolymerization and synthesis of sequence-controlled polymers.

Conclusions:

  • The developed protocol offers a new C-N bond cleavage strategy for ring-opening polymerization.
  • This method provides a facile synthetic pathway to polymers with main-chain functionalities.
  • The findings open new avenues for designing and synthesizing advanced polymer architectures.