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Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

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Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
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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

2.1K
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...
2.1K
Acid-Catalyzed Ring-Opening of Epoxides02:24

Acid-Catalyzed Ring-Opening of Epoxides

7.3K
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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Base-Catalyzed Ring-Opening of Epoxides02:26

Base-Catalyzed Ring-Opening of Epoxides

8.5K
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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Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

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The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
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Synthesis of Terpolymers at Mild Temperatures Using Dynamic Sulfur Bonds in PolyS-Divinylbenzene
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Synthesis of Terpolymers at Mild Temperatures Using Dynamic Sulfur Bonds in PolyS-Divinylbenzene

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Controlled and Regioselective Ring-Opening Polymerization for Poly(disulfide)s by Anion-Binding Catalysis.

Tianyi Du1, Boming Shen2, Jieyu Dai1

  • 1Beijing National Laboratory for Molecular Sciences, Center for Soft Matter Science and Engineering, Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China.

Journal of the American Chemical Society
|November 21, 2023
PubMed
Summary

Researchers developed a new anion-binding method to control the synthesis of poly(disulfide)s. This approach enables rapid, living ring-opening polymerization of 1,2-dithiolanes with high precision.

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Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes
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A Facile and Efficient Approach for the Production of Reversible Disulfide Cross-linked Micelles
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A Facile and Efficient Approach for the Production of Reversible Disulfide Cross-linked Micelles

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Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes
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A Facile and Efficient Approach for the Production of Reversible Disulfide Cross-linked Micelles
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A Facile and Efficient Approach for the Production of Reversible Disulfide Cross-linked Micelles

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Area of Science:

  • Polymer Chemistry
  • Materials Science
  • Organic Synthesis

Background:

  • Poly(disulfide)s are versatile sulfur-containing polymers with significant potential in medicine, energy, and functional materials.
  • The dynamic covalent disulfide (S-S) bond in poly(disulfide)s is highly reactive towards sulfide (RS-) anions, hindering controlled polymerization.
  • Existing methods struggle to manage the reactivity of the sulfide chain end, posing a challenge for synthesizing linear poly(disulfide)s.

Purpose of the Study:

  • To develop a novel strategy for controlling the synthesis of linear poly(disulfide)s by addressing the reactivity of the sulfide anion.
  • To achieve rapid, living ring-opening polymerization of 1,2-dithiolanes with high control over molecular weight distribution and regioselectivity.
  • To elucidate the mechanism of polymerization and the role of the catalyst in controlling chain propagation and monomer addition.

Main Methods:

  • Anion-binding approach utilizing a thiourea-base catalyst to complex with the sulfide chain end.
  • Ring-opening polymerization of 1,2-dithiolanes.
  • Mechanistic studies involving ternary complex formation and theoretical analyses of catalytic models.
  • Characterization of polymer properties, including dispersity and regioselectivity.

Main Results:

  • Successful control over poly(disulfide) synthesis via an anion-binding strategy, arresting the reactivity of the sulfide chain end.
  • Achieved rapid, living ring-opening polymerization of 1,2-dithiolanes, yielding polymers with narrow dispersity (Mw/Mn ≈ 1.1) and high regioselectivity (Ps ≈ 0.85).
  • Identified a thiourea-base-sulfide ternary complex as the active catalytic species, supported by mechanistic and theoretical studies.
  • Demonstrated the catalytic system's compatibility with various functional groups and its ability to produce semicrystalline polymers from lipoic acid derivatives.

Conclusions:

  • The developed anion-binding approach effectively controls the polymerization of poly(disulfide)s by managing sulfide anion reactivity.
  • The synergistic catalytic model involving a ternary complex provides a new paradigm for achieving high regioselectivity and controlled polymerization.
  • This methodology opens avenues for synthesizing advanced poly(disulfide) materials with tailored properties for diverse applications.