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Related Concept Videos

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

6.0K
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: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

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The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
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Electrophilic Aromatic Substitution: Sulfonation of Benzene01:22

Electrophilic Aromatic Substitution: Sulfonation of Benzene

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Sulfonation of benzene is a reaction wherein benzene is treated with fuming sulfuric acid at room temperature to produce benzenesulfonic acid. Fuming sulfuric acid is a mixture of sulfur trioxide and concentrated sulfuric acid.
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Reactions at the Benzylic Position: Halogenation01:11

Reactions at the Benzylic Position: Halogenation

2.5K
Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
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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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Structure of Benzene: Kekulé Model01:07

Structure of Benzene: Kekulé Model

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In 1865, August Kekule suggested the structure of benzene according to the structural theory of organic chemistry based on the three assertions—formula of benzene is C6H6, all the hydrogens of benzene are equivalent, and each carbon must have four bonds due to its tetravalency.
He proposed that benzene has a cyclic structure of six carbon atoms attached to one hydrogen atom each, with three alternating pi bonds.
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Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
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A Review on the Synthetic Methods towards Benzothienobenzothiophenes.

Nandana S K1,2, Rahul P1,2, Sheba Ann Babu1,2

  • 1Chemical Sciences and Technology Division, CSIR-National Institute for Interdisciplinary Science and Technology (CSIR-NIIST), Thiruvananthapuram, 695019, India.

Chemical Record (New York, N.Y.)
|March 8, 2024
PubMed
Summary

Benzothienobenzothiophenes (BTBTs), key organic semiconductors, offer high charge mobility for electronic devices. This review details synthetic strategies for BTBT isomers, aiding material development.

Keywords:
HeteroaceneTetracenebenzothieno[2,3-b]benzothiophenebenzothieno[3,2-b]benzothiophenesynthetic methodology

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Area of Science:

  • Organic electronics
  • Materials science
  • Heterocyclic chemistry

Background:

  • Benzothienobenzothiophenes (BTBTs) are heteroacenes with unique electronic properties.
  • Their structure, featuring two sulfur atoms, enables narrow bandgaps and efficient charge transport.
  • BTBTs are promising for organic semiconductors and field-effect transistors due to high charge carrier mobility.

Purpose of the Study:

  • To review and analyze synthetic methodologies for benzothienobenzothiophene isomers.
  • To highlight the benefits and drawbacks of various synthetic approaches.
  • To provide insights into the synthesis of BTBT analogues for material applications.

Main Methods:

  • Review of literature on synthetic strategies for BTBTs.
  • Analysis of multistep synthesis, tandem transformations, electrochemical synthesis, and annulations.
  • Examination of reaction mechanisms for isomer synthesis.

Main Results:

  • Identification of two distinct BTBT isomers based on fused benzothiophene motif locations.
  • Evaluation of the generality, advantages, and disadvantages of reported synthetic methods.
  • Comprehensive summary of synthetic routes for BTBT analogues.

Conclusions:

  • Various synthetic techniques exist for creating BTBT isomers and analogues.
  • Understanding these methods is crucial for advancing organic semiconductor materials.
  • This review serves as a guide to the synthesis of high-performance BTBT-based materials.