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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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ortho–para-Directing Deactivators: Halogens01:24

ortho–para-Directing Deactivators: Halogens

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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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Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

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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...
2.0K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

3.1K
Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
3.1K
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

3.1K
The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the...
3.1K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

2.9K
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
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Updated: Sep 18, 2025

Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
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Fluoride Ion Selective Multihydroxylated Anthracene Derivatives.

Yutian Zhang1, Mayapriveetra D/O Ponnarasu1, Pengbo Duanmu2

  • 1Department of Chemistry, National University of Singapore 3 Science Drive 3, Singapore 117543, Singapore.

ACS Omega
|June 23, 2025
PubMed
Summary

Researchers developed new fluorescent molecules from anthracene derivatives for detecting fluoride ions. These compounds offer a simple way to create sensors for environmental pollutants in water.

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Analytical Chemistry

Background:

  • Anthracene derivatives are known for their fluorescent properties.
  • Developing selective sensors for anions is crucial for environmental monitoring.
  • Catechol-containing compounds can exhibit unique electronic and optical behaviors.

Purpose of the Study:

  • To synthesize novel catechol-incorporated anthracene derivatives using a one-pot method.
  • To investigate the structure-property relationships of these synthesized molecules.
  • To evaluate their potential as fluorescent sensors for specific anions.

Main Methods:

  • One-pot synthesis involving 9-anthracenecarboxaldehyde and hydroxybenzene derivatives.
  • Acid catalysis for the reaction.
  • Density Functional Theory (DFT) calculations for regioselectivity analysis.
  • Spectroscopic characterization of the synthesized molecules.
  • Anion sensing studies in solution.

Main Results:

  • Three novel catechol-incorporated anthracene derivatives were successfully synthesized.
  • The reaction mechanism and regioselectivity were elucidated using DFT calculations.
  • The synthesized molecules demonstrated selective fluorescence response to fluoride anions.
  • The sensing was effective even in the presence of chloride and bromide ions.

Conclusions:

  • A facile one-pot synthesis provides access to functional fluorescent anthracene derivatives.
  • These molecules exhibit excellent selectivity for fluoride detection.
  • The developed compounds are promising candidates for fabricating sensors for water pollutants.