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Related Concept Videos

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

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Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
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Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

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Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
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Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

1.8K
Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation...
1.8K
ortho–para-Directing Deactivators: Halogens01:24

ortho–para-Directing Deactivators: Halogens

5.4K
Halogens are ortho–para directors. They are more electronegative than carbon. Therefore, as ring substituents, they can withdraw electrons through the inductive effect and deactivate the aromatic ring towards electrophilic substitution. Halogens also have an electron-donating resonance effect on the ring, which influences the orientation of the incoming electrophile. If an electrophile attacks at the ortho or the para position, the halogen donates electrons and stabilizes the intermediate...
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Base-Promoted α-Halogenation of Aldehydes and Ketones00:51

Base-Promoted α-Halogenation of Aldehydes and Ketones

3.4K
α-Halogenation of aldehydes and ketones is a reaction involving the substitution of α hydrogens with halogens in the presence of a base.  The reaction begins with the abstraction of  α hydrogen by the base to produce a nucleophilic enolate ion. This intermediate undergoes a subsequent nucleophilic substitution with the halogen to produce a monohalogenated carbonyl compound. If the starting substrate has more than one α hydrogen, it is difficult to stop the reaction...
3.4K
Halogenation of Alkenes02:46

Halogenation of Alkenes

15.4K
Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
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Updated: Jun 10, 2025

A Fabrication and Measurement Method for a Flexible Ferroelectric Element Based on Van Der Waals Heteroepitaxy
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Halogen Substitution Strategy for Exploiting High-Performance Molecular Ferroelectrics.

Xingguang Chen1,2, Haojie Xu1,2, Wenjing Li1,2

  • 1State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Fuzhou, Fujian, 350002, P. R. China.

Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry
|October 16, 2024
PubMed
Summary

Halogen substitution is a powerful strategy for enhancing molecular ferroelectrics. This method optimizes performance by improving polarization, Curie temperature, and bandgap in organic-inorganic hybrids and metal-free systems.

Keywords:
Bandgap engineeringHalogen substitutionMolecular ferroelectricsStructure-property relationships

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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
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Area of Science:

  • Materials Science
  • Solid-State Chemistry
  • Organic Electronics

Background:

  • Molecular ferroelectrics offer unique structural flexibility and tunability.
  • Chemical design is crucial for optimizing ferroelectric properties in molecule-based systems.
  • Halogen substitution emerges as a key strategy for property modulation.

Purpose of the Study:

  • To review recent advances in halogen substitution for molecule-based ferroelectrics.
  • To elucidate the mechanisms by which halogen substitution enhances ferroelectric performance.
  • To highlight future research directions in this field.

Main Methods:

  • Summarization of recent literature on halogen substitution in molecular ferroelectrics.
  • Analysis of organic-inorganic hybrid and metal-free molecular systems.
  • Discussion of underlying mechanisms including symmetry breaking and dipole moment optimization.

Main Results:

  • Halogen substitution effectively induces symmetry breaking and optimizes dipole moments.
  • This strategy enhances spontaneous polarization, Curie temperature, and bandgap.
  • Successful application in both organic-inorganic hybrids and metal-free molecular ferroelectrics.

Conclusions:

  • Halogen substitution is a highly effective strategy for designing and improving molecular ferroelectrics.
  • Understanding the mechanisms provides a pathway for rational material design.
  • Further exploration of halogen substitution holds significant promise for future molecular ferroelectric development.