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Related Concept Videos

Olefin Metathesis Polymerization: Overview01:13

Olefin Metathesis Polymerization: Overview

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

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

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

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

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...
Cationic Chain-Growth Polymerization: Mechanism00:57

Cationic Chain-Growth Polymerization: Mechanism

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 generated carbocation,...
Radical Chain-Growth Polymerization: Mechanism01:09

Radical Chain-Growth Polymerization: Mechanism

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 species into the...
Ziegler–Natta Chain-Growth Polymerization: Overview01:17

Ziegler–Natta Chain-Growth Polymerization: Overview

Ziegler–Natta polymerization is another form of addition or chain‐growth polymerization used for synthesizing linear polymers over branched polymers. The catalyst used for polymerization is the Ziegler–Natta catalyst, named after Karl Ziegler and Giulio Natta, who developed it in 1953. This catalyst is an organometallic complex of titanium tetrachloride and triethyl aluminum, with the active form of the catalyst being an alkyl titanium compound. Using the Ziegler–Natta catalyst, high molecular...

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Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers
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Ring-expansion metathesis polymerization: catalyst-dependent polymerization profiles.

Yan Xia1, Andrew J Boydston, Yefeng Yao

  • 1Arnold and Mabel Beckman Laboratory of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.

Journal of the American Chemical Society
|February 10, 2009
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Ring-expansion metathesis polymerization (REMP) using cyclic ruthenium catalysts shows distinct polymer growth mechanisms based on tether length. Catalyst tether length dictates whether polymerization resembles chain-growth or step-growth, influencing molecular weight evolution.

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Area of Science:

  • Polymer Chemistry
  • Organometallic Chemistry
  • Materials Science

Background:

  • Ring-expansion metathesis polymerization (REMP) is a versatile method for synthesizing cyclic polymers.
  • Cyclic ruthenium catalysts have recently emerged, offering new possibilities in REMP.
  • Understanding catalyst architecture's impact on polymerization mechanisms is crucial for controlling polymer properties.

Purpose of the Study:

  • To investigate the detailed polymerization mechanisms of REMP mediated by cyclic Ru catalysts.
  • To explore how catalyst architecture, specifically tether length, influences molecular weight evolution and polymer topology.
  • To elucidate the thermodynamic control over final polymer molecular weights in REMP.

Main Methods:

  • Synthesis and characterization of cyclic Ru catalysts with varying tether lengths (five-carbon vs. six-carbon).
  • Detailed kinetic studies of polymerization under varied reaction conditions.
  • Analysis of polymer molecular weight evolution using techniques like ICP-MS.
  • Characterization of polymer chain ends and topology using melt-state magic-angle spinning (13)C NMR spectroscopy.

Main Results:

  • Two distinct molecular weight evolutions were observed: chain-growth-like with six-carbon tethers and step-growth-like with five-carbon tethers.
  • Five-carbon-tethered catalysts showed ready release, competing with propagation and leading to step-growth behavior.
  • Final polymer molecular weights were thermodynamically controlled, reaching large ring sizes (60-120 kDa) independent of catalyst structure.
  • Six-carbon-tethered catalysts showed slow incorporation into cyclic polymers, while five-carbon-tethered catalysts had minimal incorporation.

Conclusions:

  • Catalyst tether length significantly dictates the mechanism of REMP, affecting molecular weight growth.
  • Thermodynamic equilibrium governs the final molecular weights of cyclic polymers in REMP.
  • REMP produces cyclic polymers with minimal chain ends, regardless of catalyst structure, highlighting the efficiency of the process.