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Related Concept Videos

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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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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Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

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Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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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 of a...
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Acid-Catalyzed Ring-Opening of Epoxides02:24

Acid-Catalyzed Ring-Opening of Epoxides

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Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
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Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

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The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
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A Simple and Efficient Protocol for the Catalytic Insertion Polymerization of Functional Norbornenes
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An Efficient Ring-Closure Method for Preparing Well-Defined Cyclic Polynorbornenes.

Minghui Zhang1,2, Ying Wu1, Zhengping Liu1

  • 1Institute of Polymer Chemistry and Physics, Beijing Key Laboratory of Energy Conversion and Storage Materials, College of Chemistry, Beijing Normal University, Beijing, 100875, China.

Macromolecular Rapid Communications
|December 28, 2019
PubMed
Summary

A new ring-closure method efficiently creates well-defined cyclic polynorbornenes. This technique combines living ring-opening metathesis polymerization (ROMP) with a self-accelerating click reaction (DSPAAC) for cyclic polymer synthesis.

Keywords:
bimolecular ring-closure methodcyclic polymerspolynorbornenering-opening metathesis polymerizationself-accelerating double strain-promoted azide-alkyne click reaction

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Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
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Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
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Area of Science:

  • Polymer Chemistry
  • Organic Synthesis
  • Materials Science

Background:

  • Ring-opening metathesis polymerization (ROMP) is a versatile technique for polymer synthesis.
  • Cyclic polymers offer unique properties compared to their linear counterparts.
  • Developing efficient methods for synthesizing well-defined cyclic polymers remains a challenge.

Purpose of the Study:

  • To develop an efficient bimolecular ring-closure method for preparing well-defined cyclic polynorbornenes.
  • To combine living ring-opening metathesis polymerization (ROMP) with self-accelerating double strain-promoted azide-alkyne cycloaddition (DSPAAC) for cyclic polymer synthesis.
  • To establish a novel strategy for the synthesis of cyclic polymers with defined topology.

Main Methods:

  • Synthesis of well-defined linear polynorbornenes with azide terminals using ROMP and a functionalized Grubbs initiator.
  • Modification of polymer end groups to introduce azide functionalities.
  • Ring-closure of linear polymer precursors via DSPAAC click reaction using sym-dibenzo-1,5-cyclooctadiene-3,7-diyne (DIBOD) as linkers.

Main Results:

  • Successfully prepared well-defined cyclic polynorbornenes through a bimolecular ring-closure strategy.
  • The self-accelerating DSPAAC reaction efficiently facilitated the ring-closing process.
  • Pure cyclic polynorbornenes were obtained even with an excess of DIBOD linkers.

Conclusions:

  • This study presents the first report on preparing well-defined polynorbornenes with cyclic topology using a ring-closure strategy.
  • The combined ROMP and DSPAAC approach offers an efficient route to cyclic polymers.
  • The developed method provides a powerful tool for accessing cyclic polymer architectures.