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Related Concept Videos

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

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All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
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Electrophilic Aromatic Substitution: Overview01:16

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In an electrophilic aromatic substitution reaction, an electrophile substitutes for a hydrogen of an aromatic compound.
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The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
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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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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.
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
4.8K
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

5.1K
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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Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
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Orientation-Dependent Work-Function Modification Using Substituted Pyrene-Based Acceptors.

O T Hofmann1, H Glowatzki2, C Bürker3

  • 1Institute of Solid State Physics, NAWI Graz, Graz University of Technology, Petersgasse 16, 8010 Graz, Austria.

The Journal of Physical Chemistry. C, Nanomaterials and Interfaces
|November 21, 2017
PubMed
Summary
This summary is machine-generated.

Molecular acceptors like pyrene-tetraone tune metal electrode work functions, impacting organic semiconductor charge injection. Adsorbate structure, not just electron affinity, significantly alters electronic properties.

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Area of Science:

  • Surface science
  • Materials science
  • Organic electronics

Background:

  • Work function tuning is crucial for organic electronics.
  • Molecular acceptors can modify electrode properties.
  • Understanding adsorption effects is key for device performance.

Purpose of the Study:

  • Investigate pyrene-tetraone derivatives (PyT, Br-PyT, NO2-PyT) for modifying Au(111) and Ag(111) work functions.
  • Explore the impact of molecular electron affinity and adsorbate structure on electrode electronic properties.
  • Explain deviations from expected Fermi-level pinning trends.

Main Methods:

  • Complementary theoretical and experimental approaches.
  • Photoelectron spectroscopy.
  • X-ray standing wave technique.
  • Density functional theory simulations.

Main Results:

  • Observed Fermi-level pinning trends for some interfaces.
  • Significant deviations for Br-PyT/Ag(111) and NO2-PyT/Ag(111), with a 1.6 eV work function increase for NO2-PyT/Ag(111).
  • Adsorption-induced molecular reorientation (face-on to edge-on) explains deviations.
  • Edge-on orientation leads to larger work function changes.

Conclusions:

  • Molecular orientation significantly impacts electrode electronic properties, beyond electron affinity.
  • Adsorbate structure is a critical factor in work function modification.
  • Provides comprehensive understanding for designing organic electronic devices.