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Related Concept Videos

Acid Halides to Esters: Alcoholysis01:12

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Ethers represent a class of chemical compounds that become more dangerous with prolonged storage because they tend to form explosive peroxides when standing in the air. Autoxidation is the spontaneous oxidation of a compound in air. In the presence of oxygen, ethers slowly oxidize to form hydroperoxides and dialkyl peroxides.
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In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
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Nucleophilic Aromatic Substitution: Elimination–Addition01:11

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Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
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Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

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Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

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Introduction
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Impurities in Arylboronic Esters Induce Persistent Afterglow.

Zhu Wu1,2, Christoph Herok3, Alexandra Friedrich1

  • 1Institute of Inorganic Chemistry and Institute for Sustainable Chemistry & Catalysis with Boron, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074 Würzburg, Germany.

Journal of the American Chemical Society
|November 5, 2024
PubMed
Summary
This summary is machine-generated.

Room temperature phosphorescence (RTP) in arylboronic esters is often due to impurities, not the compounds themselves. Careful purification removed RTP, but a specific impurity was found to induce long afterglows.

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Area of Science:

  • Organic Chemistry
  • Photophysics
  • Materials Science

Background:

  • Recent reports suggest arylboronic esters exhibit room temperature phosphorescence (RTP), challenging established theories of intersystem crossing.
  • This property is valuable for applications like security printing, oxygen sensing, and bioimaging.

Purpose of the Study:

  • To investigate the validity of RTP in arylboronic esters.
  • To determine if observed RTP phenomena are intrinsic properties or artifacts of impurities.

Main Methods:

  • Synthesis and purification of 12 previously reported RTP-active arylboronic esters using chromatography, recrystallization, and sublimation.
  • Photophysical property re-examination, single-crystal X-ray diffraction, and theoretical studies.
  • Isolation and identification of the impurity responsible for delayed fluorescence.

Main Results:

  • None of the 12 purified arylboronic esters exhibited persistent RTP.
  • The impurity 4-amino-3,5-bis(pinacolatoboryl)benzonitrile was identified as the source of delayed fluorescence in 3,5-bis(pinacolatoboryl)benzonitrile.
  • Doping with 1.0 mol % of the impurity induced a 67 ms afterglow via a dimer charge transfer state.

Conclusions:

  • The RTP observed in previous studies of arylboronic esters likely resulted from impurities.
  • Rigorous purification is crucial for accurate photophysical research.
  • A strategy for designing materials with long afterglows by controlled doping with specific impurities has been demonstrated.