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Related Concept Videos

Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
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Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

2.7K
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.
2.7K
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

2.3K
The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
2.3K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

11.4K
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
11.4K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

3.3K
Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
3.3K
Anionic Chain-Growth Polymerization: Overview01:20

Anionic Chain-Growth Polymerization: Overview

2.3K
The polymerization process that involves carbanion as an intermediate is called anionic polymerization. It is also a type of addition or chain-growth polymerization. Anionic polymerization gets initiated by a strong nucleophile such as an organolithium or a Grignard reagent. The most commonly used initiator for anionic polymerization is butyl lithium. Monomers involved in anionic polymerization must possess a vinyl group bonded to one or two electron-withdrawing groups. For instance,...
2.3K

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1,3,5-Triphenylbenzene and Corannulene as Electron Receptors for Lithium Solvated Electron Solutions
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Dibenzo[a,e]Cyclooctatetraene-Functionalized Polymers as Potential Battery Electrode Materials.

Gauthier Desmaizieres1, Martin E Speer1,2, Inna Thiede3

  • 1Institute for Organic Chemistry, University of Freiburg, Albertstraße 21, Freiburg, 79104, Germany.

Macromolecular Rapid Communications
|March 4, 2021
PubMed
Summary

Researchers developed new dibenzo[a,e]cyclooctatetraene (DBCOT) polymers for sustainable batteries. These organic redox polymers show promise as negative electrode materials, offering low potentials for high-voltage applications.

Keywords:
Wittig reactionanode materialscyclooctatetraenemolecular actuatorsorganic batteriesredox polymers

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Area of Science:

  • Materials Science
  • Electrochemistry
  • Polymer Chemistry

Background:

  • Organic redox polymers are crucial for developing sustainable rechargeable batteries.
  • Low-potential (<2 V vs. Li|Li+) negative electrode materials are needed for high-voltage organic cells.
  • Dibenzo[a,e]cyclooctatetraene (DBCOT) exhibits reversible two-electron reduction below 1 V vs. Li|Li+ and conformational changes upon reduction.

Purpose of the Study:

  • To synthesize novel aliphatic DBCOT-based polymers.
  • To investigate the electrochemical properties of these polymers for potential use as battery electrode materials.
  • To explore DBCOT polymers for applications beyond batteries, such as molecular actuators.

Main Methods:

  • Development of a three-step synthetic route to 2-bromo-functionalized DBCOT precursor.
  • Synthesis of three aliphatic DBCOT-polymers.
  • Electrochemical characterization using cyclic voltammetry (CV) in solution and on thin films.
  • Half-cell battery measurements.

Main Results:

  • Successful synthesis of three aliphatic DBCOT-polymers.
  • CV measurements confirmed the redox activity and low potentials of DBCOT polymers.
  • Half-cell tests revealed pseudo-capacitive behavior with significant Faradaic contributions.

Conclusions:

  • DBCOT-based polymers are promising candidates for sustainable organic battery electrodes.
  • The conformational change of DBCOT upon reduction suggests potential in molecular actuator applications.
  • Optimizing electrode composition and fabrication is key to fully realizing the redox activity of DBCOT polymers.