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Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)

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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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Olefin Metathesis Polymerization: Overview01:13

Olefin Metathesis Polymerization: Overview

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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.
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists...
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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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Regioselective Formation of Enolates01:33

Regioselective Formation of Enolates

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As depicted in the figure below, the unsymmetrical ketones can form two possible enolates:  less substituted or more substituted enolates. Usually, the thermodynamic enolates are formed from the more substituted α-carbon atom, while the kinetic enolates are formed faster by deprotonation from the less substituted position. The thermodynamic enolates have lower energy, so they are  more stable. But the energy required to form kinetic enolates is less.
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Cationic Chain-Growth Polymerization: Mechanism00:57

Cationic Chain-Growth Polymerization: Mechanism

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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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Base-Catalyzed Ring-Opening of Epoxides02:26

Base-Catalyzed Ring-Opening of Epoxides

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Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...
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Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers
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Programmable Macrocyclic Enoate-Mediated Regioselective ROMP for Sequence-Controlled Polymer Synthesis.

Ying Wang1, Yiyang Liang1, Jianhua Tang1

  • 1Department of Chemistry and Material Science, College of Science, Nanjing Forestry University, Nanjing 210037, China.

ACS Macro Letters
|July 23, 2025
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Summary

We developed a new, easily accessible macrocyclic olefin template for synthesizing sequence-controlled polymers using entropy-driven ring-opening metathesis polymerization (ED-ROMP). This method precisely controls polymer sequences for advanced material properties.

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Area of Science:

  • Polymer Chemistry
  • Macromolecular Engineering
  • Organic Synthesis

Background:

  • Entropy-driven ring-opening metathesis polymerization (ED-ROMP) is a key strategy for creating sequence-controlled polymers.
  • Traditional cyclic templates for ED-ROMP often involve complex synthesis and struggle with regio- and stereospecificity.

Purpose of the Study:

  • To develop an easily accessible macrocyclic olefin template for sequence-controlled polymerization.
  • To enable precise encoding of sequence information within polymer chains.
  • To create a model system for studying sequence-property relationships in polymers.

Main Methods:

  • Utilized olefin cross-metathesis between acrylates and terminal olefins for template synthesis.
  • Employed an iterative stepwise growth approach for precise sequence encoding.
  • Performed entropy-driven ring-opening metathesis polymerization (ED-ROMP) with the novel macrocyclic monomer.

Main Results:

  • Successfully synthesized an easily accessible macrocyclic olefin template with an enoate motif.
  • Achieved precise sequence control in polymers through iterative monomer addition.
  • Demonstrated tunable sequence compositions in the resulting sequence-controlled polymers.

Conclusions:

  • The developed macrocyclic enoate monomer is compatible with tail-to-head ED-ROMP.
  • This provides a versatile platform for precision macromolecular engineering.
  • The sequence-controlled polymers serve as valuable models for structure-property investigations.