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

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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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If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
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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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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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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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Monomer centred selectivity guidelines for sulfurated ring-opening copolymerisations.

Merlin R Stühler1,2, Marie Kreische2, Christoph Fornacon-Wood1

  • 1Makromolekulare Chemie, Universität Bayreuth Universitätsstraße 30 95447 Bayreuth Germany alex.plajer@uni-bayreuth.de.

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|October 31, 2024
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Summary
This summary is machine-generated.

Achieving controlled synthesis of sulfur-containing polymers via catalytic ring-opening copolymerization (ROCOP) is now possible. This study identifies key factors for selectivity, enabling the creation of advanced, sustainable sulfurated polymers.

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Area of Science:

  • Polymer Chemistry
  • Sustainable Materials Science
  • Organic Synthesis

Background:

  • Sulfur-containing polymers offer sustainability benefits like degradability and recyclability.
  • Current synthesis methods, particularly catalytic ring-opening copolymerization (ROCOP), lack control over microstructure and properties.
  • A predictive model for selectivity in sulfurated ROCOP is needed to advance these materials.

Purpose of the Study:

  • To investigate factors governing selectivity in sulfurated ROCOP reactions.
  • To develop strategies for controlling polymer microstructure and properties.
  • To enable the synthesis of well-defined sulfur-containing polymers.

Main Methods:

  • Exploration of ROCOP with diverse monomers: thioanhydrides/carbon disulfide and epoxides, thiiranes, oxetanes.
  • Analysis of reaction mechanisms, focusing on catalyst-bound chain ends and backbiting reactions.
  • Implementation of monomer selection, ring strain optimization, and controlled termination strategies.

Main Results:

  • Identified backbiting of catalyst-bound alkoxide chain ends as a primary source of by-products.
  • Demonstrated mitigation of by-products through specific monomer choices, maximizing ring strain, and timely termination.
  • Successfully synthesized perfectly alternating poly(esters-alt-thioesters) using ethylene oxide and various oxetanes.

Conclusions:

  • Selectivity in sulfurated ROCOP is controllable by strategic monomer selection, not solely catalyst design.
  • Mechanistic insights provide a foundation for developing future selective polymerization methods.
  • This work advances sulfurated polymers as viable, sustainable alternatives to conventional materials.