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Related Concept Videos

Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

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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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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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Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism01:14

Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism

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The Wittig reaction, which converts aldehydes or ketones to alkenes using phosphorus ylides, proceeds through a nucleophilic addition‒elimination process.
The reaction begins with the nucleophilic addition between a phosphorus ylide and the carbonyl compound. Due to its carbanionic character,  phosphorus ylide acts as a strong nucleophile and attacks the electrophilic carbonyl group. This generates a charge-separated dipolar intermediate called betaine. The negatively charged oxygen atom and...
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Oxidation of Phenols to Quinones01:17

Oxidation of Phenols to Quinones

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In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox...
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Aldehydes and Ketones to Alkenes: Wittig Reaction Overview01:19

Aldehydes and Ketones to Alkenes: Wittig Reaction Overview

7.9K
The Wittig reaction is the conversion of carbonyl compounds-aldehydes and ketones-to alkenes using phosphorus ylides, or the Wittig reagent. The reaction was pioneered by Prof. Georg Wittig, for which he was awarded the Nobel Prize in Chemistry.
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Redox Reactions01:24

Redox Reactions

55.8K
Oxidation-reduction or redox reactions involve the transfer of electrons from one molecule or atom to another. When an atom gains an electron, another atom must lose an electron, meaning oxidation and reduction must occur together. Since the redox occurs in pairs, the atom that gets oxidized is also called the reducing agent or reductant, and the atom that is reduced is also called the oxidizing agent or oxidant. A straightforward way to remember the definitions of oxidation and reduction is...
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Updated: Jul 30, 2025

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI

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Phosphine Oxide-Functionalized Terthiophene Redox Systems.

Daniel Käch1, Aurelio C Gasser1, Lionel Wettstein1

  • 1Department of Chemistry and Applied Biosciences, ETH Zürich, Vladimir-Prelog-Weg 1, 8093, Zürich, Switzerland.

Angewandte Chemie (International Ed. in English)
|May 16, 2023
PubMed
Summary
This summary is machine-generated.

Researchers developed stable phosphine oxide-functionalized terthiophenes for organic electronics. These compounds undergo controlled redox reactions at extreme potentials, enabling new energy storage applications.

Keywords:
ElectrochemistryElectronic StructureFunctional OligothiophenesMain Group RadicalsRedox Chemistry

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Area of Science:

  • Electrochemistry
  • Materials Science
  • Organic Electronics

Background:

  • Main group systems with controlled redox events at extreme potentials are crucial for organic electronics and energy storage.
  • Developing stable and reversible redox-active materials remains a significant challenge.

Purpose of the Study:

  • To synthesize and characterize novel phosphine oxide-functionalized terthiophenes.
  • To investigate their electrochemical properties, particularly their redox potentials and stability.
  • To explore their potential as components in organic electronic devices and energy storage systems.

Main Methods:

  • Synthesis of phosphine oxide-functionalized terthiophenes.
  • Electrochemical characterization including cyclic voltammetry and galvanostatic charge-discharge cycling.
  • Spectroscopic analysis (e.g., EPR, UV-Vis) to study radical anions.
  • Computational modeling to understand redox mechanisms and electronic structure.

Main Results:

  • Developed terthiophene derivatives exhibiting two reversible one-electron (1e-) reductions below -2 V vs Fc/Fc+.
  • Synthesized and characterized a stable phosphine oxide-functionalized terthiophene radical anion.
  • Identified a derivative with exceptional stability during bulk two-electron (2e-) galvanostatic cycling.
  • Established a new class of multi-electron redox systems based on main group elements.

Conclusions:

  • Phosphine oxide-functionalized terthiophenes represent a new class of stable, multi-electron redox systems.
  • These materials expand the achievable electrochemical cell potential range for main group electrolytes.
  • The findings offer promising avenues for advanced organic electronics and high-performance energy storage solutions.