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Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

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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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VSEPR Theory and the Effect of Lone Pairs04:01

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Effect of Lone Pairs of Electrons on Molecule Geometry
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Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

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Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
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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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Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

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Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
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Halogenation of Alkenes02:46

Halogenation of Alkenes

18.2K
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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Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
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Unilaterally Fluorinated Acenes: Synthesis and Solid-State Properties.

Philipp E Hofmann1, Matthias W Tripp1, Daniel Bischof2

  • 1Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Straße 4, 35043, Marburg, Germany.

Angewandte Chemie (International Ed. in English)
|June 9, 2020
PubMed
Summary
This summary is machine-generated.

Researchers developed a new method for functionalizing organic semiconductor molecules, creating novel fluorinated acenes. These new materials bridge properties between pentacene and perfluoropentacene, impacting crystal packing and solid-state characteristics.

Keywords:
aceneselectronic structurefluorinated acenessolid-state structuresunilateral substitution

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Area of Science:

  • Organic electronics
  • Materials science
  • Supramolecular chemistry

Background:

  • Organic electronics rely on molecular materials with tailored electronic properties.
  • Acenes are key organic semiconductors, but their functionalization is challenging.
  • Unilateral functionalization offers new design possibilities.

Purpose of the Study:

  • To develop a novel synthetic route for unilateral functionalization of acenes.
  • To synthesize and characterize novel fluorinated acenes: hexafluoropentacene and pentafluorotetracene.
  • To investigate the structure-property relationships of these new materials.

Main Methods:

  • Organic synthesis of fluorinated acenes.
  • Quantum chemical Density Functional Theory (DFT) calculations.
  • Optical and X-ray absorption spectroscopy.
  • Crystal structure analysis and Hirshfeld surface analysis.

Main Results:

  • Successful synthesis of 1,2,10,11,12,14-hexafluoropentacene and 1,2,9,10,11-pentafluorotetracene.
  • Hexafluoropentacene exhibits single-molecule properties intermediate between pentacene and perfluoropentacene.
  • Fluorination induced a different crystal packing motif due to specific F⋅⋅⋅H interactions.
  • Altered solid-state properties including exciton binding energy and sublimation enthalpy.

Conclusions:

  • The novel synthetic route enables precise control over acene functionalization.
  • Fluorinated acenes offer tunable electronic and solid-state properties.
  • Understanding intermolecular interactions is crucial for designing organic electronic materials.