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Related Concept Videos

Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

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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.
Removing one hydrogen from the intervening CH2 group...
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Radical Reactivity: Steric Effects01:10

Radical Reactivity: Steric Effects

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The presence of electron-donating, electron-withdrawing, or conjugating groups adjacent to a radical center, imparts electronic stabilization to the radicals. Examples of such electronically-stabilized radicals are triphenylmethyl, tetramethylpiperidine‐N‐oxide, and 2,2‐diphenyl‐1‐picrylhydrazyl. These radicals are remarkably stable and are known as persistent radicals. Some of the persistent radicals can even be isolated and purified.
Along with electronic...
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Radicals: Electronic Structure and Geometry01:07

Radicals: Electronic Structure and Geometry

4.9K
This lesson delves into the geometry of a radical, which is influenced by the electronic structure of the molecule. The principle is similar to that of a lone pair, where the unpaired electron influences the geometry at the radical center.
Accordingly, the structure of a trivalent radical lies between the geometries of carbocations and carbanions. An sp2-hybridized carbocation is trigonal planar, while an sp3-hybridized carbanion is trigonal pyramidal. Here, the difference in geometry is...
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Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

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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...
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π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds01:14

π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds

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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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Radical Reactivity: Intramolecular vs Intermolecular01:33

Radical Reactivity: Intramolecular vs Intermolecular

2.1K
Radical reactions can occur either intermolecularly or intramolecularly. In an intermolecular radical reaction, a nucleophilic radical adds to an electrophilic alkene or vice versa. In such reactions, the radical and generally the alkene, which is also called the radical trap, are two different molecules. Additionally, for such intermolecular reactions to occur, the radical trap must be active, present in an excess concentration, and the radical starting material must have a weak...
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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A Spherically Shielded Triphenylamine and Its Persistent Radical Cation.

Tobias A Schaub1, Theresa Mekelburg2, Pavlo O Dral3

  • 1Institute of Organic Chemistry, Ruprecht-Karls-University Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|January 24, 2020
PubMed
Summary

Researchers designed a stable triphenylamine radical cation using steric protection. This shielded molecule exhibits reversible oxidation and unique photophysical properties, paving the way for new electronic materials.

Keywords:
bridged triphenylaminespolycyclic systemsradical cationsspirocycles

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Electrochemistry

Background:

  • Triphenylamine derivatives are crucial in organic electronics.
  • Controlling the stability and reactivity of radical cations is essential for their application.
  • Steric hindrance is a key strategy for stabilizing reactive intermediates.

Purpose of the Study:

  • To design and synthesize a sterically protected triphenylamine scaffold.
  • To investigate the stability and properties of its one-electron oxidized radical cation.
  • To understand the impact of structural modifications on electronic and photophysical characteristics.

Main Methods:

  • Synthesis of sterically protected triphenylamine.
  • Electrochemical oxidation and spectroelectrochemistry.
  • Electron paramagnetic resonance (EPR) spectroscopy.
  • X-ray crystallography and density functional theory (DFT) calculations.

Main Results:

  • A stable, planarized triphenylamine radical cation was successfully synthesized.
  • The radical cation shows reversible oxidation at moderate potentials (+0.38 V).
  • It exhibits a distinct visible absorption and remarkable stability, lasting for weeks.
  • Experimental and computational studies elucidated the structural and electronic effects of oxidation.

Conclusions:

  • Steric protection effectively stabilizes the triphenylamine radical cation.
  • The shielded radical cation possesses desirable properties for potential applications.
  • The study provides insights into molecular design for stable radical species.