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Related Concept Videos

Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

7.3K
Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.
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Types of Chemical Reactions: Exchange and Reversible01:08

Types of Chemical Reactions: Exchange and Reversible

10.1K
An exchange reaction is a chemical reaction in which both synthesis and decomposition occur, chemical bonds are both formed and broken, and chemical energy is absorbed, stored, and released.
A special kind of exchange reaction is the oxidation-reduction reaction, or the redox reaction. These reactions involve the transfer of electrons from one compound to another. The electrons in these reactions commonly come from hydrogen atoms, which consist of an electron and a proton. A molecule gives up a...
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Phosphodiester Linkages01:01

Phosphodiester Linkages

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Overview
Phosphodiester bond forms when a phosphoric acid molecule (H3PO4) links with two hydroxyl groups (–OH) of two other molecules, forming two ester bonds. Two water molecules are released in this process. The phosphodiester bond is commonly found in nucleic acids (DNA and RNA) and plays a critical role in their structure and function.
Phosphodiester Bonds Link Nucleotides Together
DNA and RNA are polynucleotides or long chains of nucleotides that are linked together. A nucleotide is...
109.3K
SN2 Reaction: Mechanism02:27

SN2 Reaction: Mechanism

16.9K
The kinetic studies of SN2 reactions suggest an essential feature of its mechanism: it is a single-step process without intermediates. Here, both the nucleophile and the substrate participate in the rate-determining step.
The presence of the more electronegative halogen in the substrate creates a polarized carbon-halide bond. The halide pulls the electron cloud generating an electrophilic center at the carbon atom. Thus, the carbon atom carries a partial positive charge while the halide has a...
16.9K
Dynamic Equilibrium02:20

Dynamic Equilibrium

61.0K
A reversible chemical reaction represents a chemical process that proceeds in both forward (left to right) and reverse (right to left) directions. When the rates of the forward and reverse reactions are equal, the concentrations of the reactant and product species remain constant over time and the system is at equilibrium. A special double arrow is used to emphasize the reversible nature of the reaction. The relative concentrations of reactants and products in equilibrium systems vary greatly;...
61.0K
Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

5.6K
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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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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Thiol-Anhydride Dynamic Reversible Networks.

Maciej Podgórski1,2, Sudheendran Mavila1, Sijia Huang1

  • 1Department of Chemical and Biological Engineering, University of Colorado, UCB 596, Boulder, 80309, CO, USA.

Angewandte Chemie (International Ed. in English)
|March 6, 2020
PubMed
Summary
This summary is machine-generated.

This study demonstrates reversible thiol-anhydride chemistry for creating adaptable networks. These covalent adaptable networks (CANs) offer tunable properties and enable efficient material reprocessing and recycling.

Keywords:
covalent adaptable networksdynamic compositesphotopolymersrecyclingstress relaxation

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Area of Science:

  • Polymer Chemistry
  • Materials Science
  • Organic Chemistry

Background:

  • Thiol-anhydride reactions form reversible thioester bonds.
  • This reversibility is key for developing dynamic covalent chemistry.
  • Covalent adaptable networks (CANs) offer tunable material properties.

Purpose of the Study:

  • To investigate the fabrication of covalent adaptable networks (CANs) using thiol-anhydride chemistry.
  • To explore the dynamic characteristics and reprocessing capabilities of these materials.
  • To evaluate the influence of varying reaction parameters on network properties.

Main Methods:

  • Utilized maleic, succinic, and phthalic anhydride derivatives as bifunctional reactants.
  • Synthesized thiol-anhydride elastomers, glasses, composites, and photopolymers.
  • Investigated stress relaxation, reprocessing, and recycling under varied conditions.

Main Results:

  • Achieved 100% stress relaxation within minutes to hours at mild temperatures (80-120°C).
  • Demonstrated full recovery of pristine material properties after up to five reprocessing cycles.
  • Showcased tunable dynamic covalent chemistry in various material formats.

Conclusions:

  • Thiol-anhydride chemistry provides a robust platform for creating highly adaptable and recyclable materials.
  • The developed CANs exhibit excellent dynamic properties, including rapid stress relaxation and recyclability.
  • This approach facilitates sustainable material design through efficient reprocessing and property retention.