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Related Concept Videos

Electrophilic Aromatic Substitution: Sulfonation of Benzene01:22

Electrophilic Aromatic Substitution: Sulfonation of Benzene

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.
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

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.
Crown Ethers02:36

Crown Ethers

Crown ethers are cyclic polyethers that contain multiple oxygen atoms, usually arranged in a regular pattern. The first crown ether was synthesized by Charles Pederson while working at DuPont in 1967. For this work, Pedersen was co-awarded the 1987 Nobel Prize in Chemistry. Crown ethers are named using the formula x-crown-y, where x is the total number of atoms in the ring and y is the number of ether oxygen atoms. The term 'crown' refers to the crown-like shape that these ether molecules take.
Nomenclature of Aromatic Compounds with a Single Substituent01:23

Nomenclature of Aromatic Compounds with a Single Substituent

Benzene is the simplest aromatic hydrocarbon or arene. The IUPAC names for simple monosubstituted benzene derivatives are derived by adding the substituent's name as a prefix to the parent benzene. For example, halobenzene, where the halogen could be fluoro (F), chloro (Cl), bromo (Br), and iodo (I).
NMR Spectroscopy of Benzene Derivatives01:37

NMR Spectroscopy of Benzene Derivatives

Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling constants depend...
Nomenclature of Aromatic Compounds with Multiple Substituents01:11

Nomenclature of Aromatic Compounds with Multiple Substituents

When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present.
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...

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Updated: May 21, 2026

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of &#945;,&#946;-Unsaturated Compounds and Alkynes
05:34

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes

Published on: December 16, 2019

Water-soluble ionic benzoporphyrins.

Lin Jiang1, Ross A Zaenglein, James T Engle

  • 1Department of Chemistry and Biochemistry, Miami University, Oxford, OH 45056, USA.

Chemical Communications (Cambridge, England)
|June 8, 2012
PubMed
Summary
This summary is machine-generated.

Novel water-soluble tetrabenzoporphyrins were synthesized using a Heck reaction cascade. These new compounds exhibit enhanced optical properties and high water solubility, making them promising for various applications.

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Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Photochemistry

Background:

  • Porphyrins are versatile macrocyclic compounds with diverse applications.
  • Developing water-soluble porphyrins is crucial for biological and environmental applications.
  • Tetrabenzoporphyrins offer unique photophysical properties.

Purpose of the Study:

  • To synthesize novel ionic water-soluble tetrabenzoporphyrins.
  • To investigate the optical properties of these newly synthesized porphyrins.
  • To confirm the high water solubility of the target compounds.

Main Methods:

  • Synthesis via a cascade reaction employing the Heck reaction.
  • Characterization using UV-Vis spectroscopy.
  • Assessment of water solubility.

Main Results:

  • Successful synthesis of novel ionic water-soluble tetrabenzoporphyrins.
  • UV-Vis spectra showed red-shifted and broadened Soret bands.
  • Significantly enhanced Q bands were observed, indicating altered electronic properties.
  • The synthesized porphyrins demonstrated high water solubility.

Conclusions:

  • The Heck reaction cascade is an effective method for synthesizing water-soluble tetrabenzoporphyrins.
  • The new porphyrins possess favorable optical characteristics.
  • These water-soluble tetrabenzoporphyrins are suitable for applications requiring aqueous media.