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Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

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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,...
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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.
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Adrenergic Agonists: Chemistry and Structure-Activity Relationship01:16

Adrenergic Agonists: Chemistry and Structure-Activity Relationship

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Adrenergic agonists' structure-activity relationship (SAR) determines their selectivity and efficacy. These agonists comprise a phenylethylamine moiety with an aromatic ring and an ethylamine side chain.
Aromatic ring substitutions: Substituting the aromatic ring with –OH groups at positions 3 and 4 yields catecholamines (e.g., epinephrine), which have a high affinity for adrenoceptors. Hydrogen bonding between –OH groups and receptors enhances adrenergic activity.
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ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

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

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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...
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The inscribed polygon method is consistent with Hückel’s 4n + 2 rule and helps to learn whether the given cyclic compound is aromatic or not. The compound is stable and aromatic if every bonding molecular orbital (MO) is completely filled with a pair of electrons. However, if the non-bonding or antibonding orbitals are filled with electrons, the compound is unstable and not aromatic. Consider the Frost circle diagrams for cycloalkenes containing 4 to 8 carbons.
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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...
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Emerging Trends in Phenothiazine Embedded Macrocycles.

Neha Tripathi1, Mangalampalli Ravikanth1

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

Chemical Record (New York, N.Y.)
|October 10, 2025
PubMed
Summary

Phenothiazine macrocycles combine unique photophysical and redox properties for advanced applications. This review details their synthesis, structure, and properties, encouraging further research in this promising area.

Keywords:
calix[n]phenothiazinescyclic phenothiazine arraysmacrocyclic cages

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Phenothiazines are electron-rich heterocyclic compounds vital in pharmaceuticals, dyes, and electronics.
  • Their electron-donating nature enables charge-transfer salt formation and fast electron transfer.
  • Phenothiazines serve as photoactive materials in organic light-emitting devices and solar cells.

Purpose of the Study:

  • To review the synthesis, structure, and properties of phenothiazine-embedded macrocycles.
  • To highlight the potential applications of these novel materials.
  • To stimulate further research in phenothiazine-containing macrocyclic chemistry.

Main Methods:

  • Literature review of recent advancements in phenothiazine macrocycle synthesis.
  • Analysis of structural and physicochemical properties of various phenothiazine macrocycles.
  • Compilation of diverse examples including calix[n]phenothiazines, imine-bridged macrocycles, cyclophanes, crown ethers, and porphyrinoids.

Main Results:

  • Various phenothiazine-embedded macrocycles have been successfully synthesized.
  • These macrocycles exhibit interesting photophysical and redox characteristics.
  • Exploitation of their structure and properties for diverse applications is ongoing.

Conclusions:

  • Phenothiazine-containing macrocycles represent a significant area of research due to their unique properties.
  • Continued exploration of their synthesis and applications is warranted.
  • These materials hold promise for future innovations in various scientific and technological fields.