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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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Preparation and Reactions of Sulfides02:26

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Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
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Phase II Reactions: Sulfation and Conjugation with α-Amino Acids01:19

Phase II Reactions: Sulfation and Conjugation with α-Amino Acids

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Sulfation and α-amino acid conjugation are two critical biotransformation reactions in drug metabolism. Sulfation, a phase II biotransformation reaction, involves adding a polar sulfate group to a drug, enhancing its water solubility and promoting excretion. This process can either co-occur with or occur independently of glucuronidation. Nonmicrosomal sulfotransferase enzymes catalyze the process. The reaction involves 3'-phosphoadenosine-5'-phosphosulfate or PAPS coenzyme...
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Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

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Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
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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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Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

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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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Functionalization and solubilization of polycyclic aromatic compounds by sulfoniumization.

Johannes E Erchinger1, Tsubasa Okumura2, Kanami Nakata2

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|April 24, 2025
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Researchers developed a sulfoniumization method to improve the solubility and functionality of polycyclic aromatic hydrocarbons (PAHs). This strategy enables new applications in materials science and bio-imaging, including selective mitochondrial staining.

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Polycyclic Aromatic Hydrocarbons (PAHs) possess unique properties valuable for materials science.
  • Poor solubility of PAHs hinders their functionalization and broader application.
  • Developing soluble PAH derivatives is crucial for advancing materials and chemical research.

Purpose of the Study:

  • To develop a novel sulfoniumization strategy for solubilizing and functionalizing diverse PAHs.
  • To demonstrate the versatility of the method for creating functional PAH derivatives.
  • To explore the application of these novel compounds in bio-imaging.

Main Methods:

  • A one-step sulfoniumization protocol using a triethylene glycol ether-substituted diaryl sulfoxide.
  • Modification of reaction conditions to achieve mono- and bis-sulfoniumization.
  • Post-functionalization reactions including C-C and C-heteroatom bond formation.
  • Annulative π-extension (APEX) reactions for synthesizing extended PAHs.
  • Evaluation of PAH sulfonium salts in bio-imaging applications.

Main Results:

  • Successful solubilization and functionalization of various PAHs via sulfoniumization.
  • Demonstrated control over mono- and bis-sulfoniumization.
  • Synthesized complex PAH structures, including tetra-tert-butylquaterrylene, using APEX.
  • Achieved red-shifted absorption and fluorescence properties in PAH sulfonium salts.
  • Exhibited high water solubility and selective mitochondrial staining in bio-imaging with no observed cytotoxicity.

Conclusions:

  • The sulfoniumization strategy offers a versatile approach to overcome PAH solubility limitations.
  • The resulting PAH sulfonium salts are amenable to diverse post-functionalization and APEX reactions.
  • These novel PAH derivatives show promise for advanced materials and selective bio-imaging applications.