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Related Concept Videos

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

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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.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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Olefin Metathesis Polymerization: Overview01:13

Olefin Metathesis Polymerization: Overview

2.1K
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.
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists...
2.1K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

3.5K
Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
10.1K
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

2.7K
The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
2.7K

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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
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Catalyst-Free Dynamic Covalent C=C/C=N Metathesis Reaction for Associative Covalent Adaptable Networks.

Pengyun Li1, Xin Jiang1, Ruirui Gu1

  • 1Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, Institute of Fine Chemicals, School of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237, P. R. China.

Angewandte Chemie (International Ed. in English)
|June 3, 2024
PubMed
Summary

New covalent adaptable networks (CANs) utilize a catalyst-free metathesis reaction in polyurethanes. These adaptable polymers offer enhanced stability, recyclability, and shape memory capabilities for advanced material applications.

Keywords:
C=C/C=N metathesisassociativecovalent adaptable networksreprocessabilityshape memory polymer

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Area of Science:

  • Polymer Chemistry
  • Materials Science
  • Organic Chemistry

Background:

  • Thermosetting polymers traditionally suffer from irreversible cross-linking, limiting their recyclability and repairability.
  • Covalent adaptable networks (CANs) offer a solution by incorporating dynamic covalent bonds that can reversibly break and reform.
  • Existing dynamic chemistries often require catalysts or exhibit limited stability, hindering practical applications.

Purpose of the Study:

  • To introduce a novel, catalyst-free C=C/C=N metathesis reaction into thermosetting polyurethanes to create advanced CANs.
  • To investigate the impact of this dynamic exchange on material properties, including stability, solvent resistance, and mechanical performance.
  • To explore the potential of these CANs for recyclability and shape memory applications.

Main Methods:

  • Synthesis of thermosetting polyurethanes incorporating a catalyst-free C=C/C=N metathesis dynamic covalent chemistry.
  • Characterization of the resulting CANs, evaluating their stability, solvent resistance, thermal, and mechanical properties.
  • Assessment of stress-relaxation behavior and tunability through substituent modification.
  • Evaluation of recyclability and shape memory performance.

Main Results:

  • Successful creation of CANs with superior stability, solvent resistance, and thermal/mechanical properties compared to traditional thermosets.
  • Significantly accelerated stress-relaxation rates due to the C=C/C=N metathesis, tunable via ortho-substituent modification.
  • Demonstrated recyclability without compromising chemical structure or mechanical integrity.
  • Achieved complex shape memory functions enabled by the material's plasticity.

Conclusions:

  • The catalyst-free C=C/C=N metathesis reaction is a viable and effective dynamic crosslinker for creating high-performance CANs in polyurethanes.
  • These novel CANs exhibit excellent recyclability and enable sophisticated shape memory effects, addressing key limitations of conventional thermosets.
  • This dynamic chemistry opens new avenues for developing malleable, functional, and sustainable thermoset polymers.