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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.
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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: Acyclic Diene Metathesis (ADMET)00:53

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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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Free-Radical Chain Reaction and Polymerization of Alkenes02:35

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The conversion of alkenes to macromolecules called polymers is a reaction of high commercial importance. The structure of the polymer is defined by a repeating unit, while the terminal groups are considered insignificant. The average degree of polymerization represents the number of repeating units in the polymer molecule and is denoted by the subscript n.
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Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

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Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
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Radical Chain-Growth Polymerization: Mechanism01:09

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The radical chain-growth polymerization mechanism consists of three steps: initiation, propagation, and termination of polymerization. The polymerization initiates when a free radical generated from the radical initiator adds to the unsaturated bond in the monomer. The unpaired electron of the free radical and one π electron in the unsaturated bond creates a σ bond between the free radical and the monomer. As a result, the other π electron in the unsaturated bond converts this...
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Ring Expansion Alkyne Metathesis Polymerization.

Andrew M Beauchamp1, Jhonti Chakraborty1, Ion Ghiviriga2

  • 1Department of Chemistry, Center for Catalysis, University of Florida, Gainesville, Florida 32611, United States.

Journal of the American Chemical Society
|October 9, 2023
PubMed
Summary
This summary is machine-generated.

Researchers report a novel tethered alkylidyne tungsten complex enabling ring expansion alkyne metathesis polymerization (REAMP). This new catalyst successfully synthesized cyclic polymers from strained cycloalkynes, confirmed by advanced characterization techniques.

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Area of Science:

  • Organometallic Chemistry
  • Polymer Chemistry
  • Catalysis

Background:

  • Tungsten alkylidyne complexes are crucial catalysts in alkyne metathesis.
  • Ring expansion alkyne metathesis polymerization (REAMP) offers a route to cyclic polymers.
  • Development of novel catalysts is essential for advancing polymerization techniques.

Purpose of the Study:

  • To synthesize and characterize a novel tethered alkylidyne tungsten complex.
  • To investigate the complex's activity in ring expansion alkyne metathesis polymerization (REAMP).
  • To demonstrate the synthesis of cyclic polymers using this new catalytic system.

Main Methods:

  • Synthesis of tethered alkylidyne tungsten complex 7 from precursor 6 and proligand 5.
  • Characterization using Nuclear Magnetic Resonance (NMR) spectroscopy and Nuclear Overhauser Effect (NOE) spectroscopy.
  • Polymerization of strained cycloalkyne 8 followed by Size Exclusion Chromatography (SEC) and intrinsic viscosity (η) measurements.

Main Results:

  • A dimeric tethered alkylidyne tungsten complex (7) was successfully synthesized and characterized.
  • Complex 7 demonstrated activity in catalyzing the polymerization of a strained cycloalkyne (8).
  • The resulting polymers exhibited cyclic topology, confirmed by SEC and viscosity measurements.

Conclusions:

  • A novel tethered alkylidyne tungsten complex has been developed for REAMP.
  • This catalyst system is effective in producing cyclic polymers from strained cycloalkynes.
  • The findings open new avenues for synthesizing cyclic polymer architectures.