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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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Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

2.5K
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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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

8.2K
Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

1.9K
The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
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[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
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Recoverable Reusable Polyisobutylene (PIB)-Bound Ruthenium Bipyridine (Ru(PIB-bpy)3Cl2) Photoredox Polymerization

Nilusha Priyadarshani1, Yannan Liang1, Jakkrit Suriboot1

  • 1Department of Chemistry, Texas A&M University, College Station, Texas, 77842-3012, United States.

ACS Macro Letters
|May 18, 2022
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Summary
This summary is machine-generated.

Researchers developed novel polyisobutylene (PIB)-bound ruthenium bipyridine catalysts for photoredox polymerization. These soluble, recyclable catalysts significantly reduce ruthenium contamination in polyacrylate products.

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Area of Science:

  • Polymer Chemistry
  • Catalysis
  • Materials Science

Background:

  • Ruthenium bipyridine complexes are effective photoredox catalysts.
  • Achieving catalyst recyclability and minimizing metal leaching remains a challenge in polymerization.
  • Developing soluble and easily separable catalysts is crucial for sustainable chemical processes.

Purpose of the Study:

  • To synthesize and characterize polyisobutylene (PIB)-bound ruthenium bipyridine ([Ru(PIB-bpy)3]2+) metal complexes.
  • To evaluate the performance of these novel complexes as soluble, recyclable photoredox catalysts in free radical polymerization.
  • To assess the extent of ruthenium leaching and compare it with conventional low molecular weight catalysts.

Main Methods:

  • Preparation of PIB ligands via alkylation of 4,4'-dimethylbipyridine with polyisobutylene bromide.
  • Synthesis of [Ru(PIB-bpy)3]2+ complexes.
  • Photoredox polymerization of acrylate monomers under visible light irradiation using ethyl 2-bromoisobutyrate as initiator and diisopropylethylamine as base.
  • Quantification of ruthenium contamination in the resulting polyacrylate products using appropriate analytical techniques.
  • Recyclability studies of the PIB-bound catalyst.

Main Results:

  • Successfully synthesized soluble [Ru(PIB-bpy)3]2+ complexes containing PIB ligands.
  • Demonstrated the efficacy of these complexes as photoredox catalysts in the free radical polymerization of acrylates at 25 °C under visible light.
  • Achieved polyacrylate products with exceptionally low ruthenium contamination (approx. 1 ppm).
  • Showcased the catalyst's recyclability and a significant reduction (approx. 50-fold) in ruthenium leaching compared to a low molecular weight analogue, Ru(bpy)3(PF6)2.

Conclusions:

  • Polyisobutylene-bound ruthenium bipyridine complexes represent a highly effective system for soluble, recyclable photoredox catalysis.
  • This approach offers a sustainable alternative for polymerization, minimizing metal contamination and enhancing catalyst reusability.
  • The developed catalysts pave the way for greener and more efficient polymerization processes.