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Related Concept Videos

Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

3.2K
Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
3.2K
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

4.5K
Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
4.5K
Criteria for Aromaticity and the Hückel 4n + 2 Rule01:20

Criteria for Aromaticity and the Hückel 4n + 2 Rule

11.6K
Like benzene, cyclobutadiene and cyclooctatetraene are cyclic compounds with alternate single and double bonds. However, their chemical behavior differs from benzene, as they are unstable and not aromatic. So, what are the structural characteristics of unsaturated compounds categorized as aromatic?  
For the first time, Eric Hückel, a German chemical physicist, derived a set of structural features for a compound to be classified as aromatic. This is now known as...
11.6K
π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds01:14

π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds

1.4K
In aromatic compounds, such as benzene, the circulation of (4n + 2) π-electrons sets up a diamagnetic or diatropic ring current around the perimeter of the molecule. This current induces a magnetic field that opposes the external field inside the ring and reinforces it on the outside. The protons in benzene are deshielded and exhibit high chemical shifts in the range 6.5–8.5 ppm. The shielding effect at the center of the ring is evident in complex aromatic molecules, such as...
1.4K
Physical Properties of Amines01:26

Physical Properties of Amines

3.6K
Amines with low molecular weight are usually gaseous at room temperature, while those with high molecular weight are liquid or solids in nature. Usually, low molecular weight amines have a rotten fish-like smell. Diamines typically have a pungent smell. For instance, cadaverine and putrescine, depicted in Figure 1, are two molecules responsible for decaying tissue.
3.6K
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

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Related Experiment Video

Updated: Oct 4, 2025

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

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Phenothiazine-Embedded Hexaphyrins.

Avisikta Sinha1, Mangalampalli Ravikanth1

  • 1Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India.

Organic Letters
|February 7, 2022
PubMed
Summary

Novel phenothiazine-embedded porphyrinoids were synthesized, showing unique twisted structures that limit electron delocalization. These stable macrocycles display distinct optical properties and an electron-rich nature, confirmed by theory and experiments.

Area of Science:

  • Organic Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Porphyrinoids are versatile macrocyclic compounds with applications in various fields.
  • Incorporating heteroaromatic units can tune the electronic and optical properties of macrocycles.
  • Stable, nonaromatic porphyrinoid systems are of interest for novel material development.

Purpose of the Study:

  • To synthesize unprecedented nonaromatic stable phenothiazine-embedded porphyrinoids.
  • To investigate the structural, electronic, and optical properties of these novel macrocycles.
  • To explore the impact of phenothiazine incorporation on the hexaphyrin framework.

Main Methods:

  • Chemical synthesis of phenothiazine-embedded hexaphyrinoids.
  • X-ray crystallography for structural elucidation.

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  • UV-Vis-NIR absorption spectroscopy for optical characterization.
  • Electrochemical studies (e.g., cyclic voltammetry) for electronic properties.
  • Theoretical calculations (e.g., DFT) to complement experimental data.

    • Main Results:

    • Successful synthesis of stable, nonaromatic phenothiazine-containing porphyrinoids.
    • Crystal structure revealed a twisted macrocyclic conformation with planar phenothiazine units.
    • Incorporation of phenothiazine hindered extensive π-delocalization across the macrocycle.
    • Observed distinct absorption bands in the visible-near-infrared spectrum.
    • Electrochemical data confirmed the electron-rich nature of the synthesized macrocycles.
    • Theoretical studies aligned with experimental findings.

    Conclusions:

    • The study presents a novel class of stable, nonaromatic phenothiazine-embedded porphyrinoids.
    • The twisted conformation and localized π-system influence the material's properties.
    • These findings open avenues for designing new functional organic materials with tailored optoelectronic characteristics.