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Related Concept Videos

Oxidation of Phenols to Quinones01:17

Oxidation of Phenols to Quinones

In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox property is crucial in...
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

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

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

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...
Structure of Porins01:21

Structure of Porins

Mitochondria, chloroplasts, and gram-negative bacteria have transmembrane, beta-barrel proteins called porins to mediate the free diffusion of ions and metabolites across the membrane. Mitochondrial porin precursors contain conserved amino acid sequences called beta signals at their C-terminal. Beta signals have a  motif of PoXGXXHyXHy (Po-Polar, X-Any amino acid, G-Glycine, Hy-LargeHydrophobic), which are crucial for precursor recognition to initiate precursor assembly. Beta-barrel precursors...

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Related Experiment Video

Updated: Jun 4, 2026

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

Quinoline-annulated porphyrins.

Joshua Akhigbe1, Matthias Zeller, Christian Brückner

  • 1Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269-3060, United States.

Organic Letters
|February 17, 2011
PubMed
Summary

Researchers synthesized novel quinoline-annulated porphyrins from porphyrin-2,3-dione dioximes. These porphyrinoids exhibit red-shifted UV-vis spectra due to an extended π-system and nonplanar structures.

Area of Science:

  • Organic Chemistry
  • Materials Science
  • Photochemistry

Background:

  • Porphyrins are vital macrocyclic compounds with diverse applications.
  • Annulated porphyrins offer tunable electronic and optical properties.
  • Developing novel porphyrinoid structures is crucial for advanced materials.

Purpose of the Study:

  • To synthesize novel mono- and bis-quinoline-annulated porphyrins and their N-oxides.
  • To investigate the photophysical properties of these new porphyrinoids.
  • To characterize the structural features of the synthesized compounds.

Main Methods:

  • Utilizing porphyrin-2,3-dione mono- and dioximes as starting materials.
  • Employing efficient synthetic strategies for annulation and N-oxidation.

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Facile Preparation of 4-Substituted Quinazoline Derivatives

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  • Characterizing novel chromophores using UV-vis spectroscopy.
  • Determining molecular structure via X-ray crystallography.

    • Main Results:

    • Successful synthesis of mono- and bis-quinoline-annulated porphyrins and N-oxides.
    • Observation of significantly red-shifted UV-vis spectra compared to parent porphyrins.
    • Demonstration of nonplanar macrocyclic conformation through crystal structure analysis.
    • Extended π-system contributes to altered electronic properties.

    Conclusions:

    • Novel quinoline-annulated porphyrins and N-oxides were efficiently synthesized.
    • These porphyrinoids possess unique photophysical properties due to extended π-systems.
    • Structural characterization confirms nonplanar conformations, influencing their properties.
    • This work expands the library of functional porphyrinoid chromophores.