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Related Concept Videos

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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Radical Reactivity: Overview01:11

Radical Reactivity: Overview

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Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired...
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Radical Formation: Overview01:03

Radical Formation: Overview

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A bond can be broken either by heterolytic bond cleavage to form ions or homolytic bond cleavage to yield radicals. A fishhook arrow is used to represent the motion of a single electron in homolytic bond cleavage. There are two main sources from which radicals can be formed:
Radicals from spin-paired molecules:
Radicals can be obtained from spin-paired molecules either by homolysis or electron transfer. While two radicals are formed in the former, an electron is added in the...
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Radical Formation: Addition00:47

Radical Formation: Addition

2.3K
Radicals can be formed by adding a radical to a spin-paired molecule. This is typically observed with unsaturated species, where the addition of a radical across the π bond leads to the production of a new radical by dissolving the π bond. For example, the addition of a Br radical to an alkene yields a carbon-centered radical.
Similar to charge conservation in chemical reactions, spin conservation is implicit for radical reactions. Accordingly, the product formed must possess an...
2.3K
Radical Formation: Abstraction00:47

Radical Formation: Abstraction

4.4K
The electron of an atom can be abstracted from a compound by a relatively unstable radical to generate a new radical of relatively greater stability. For example, an initiator which forms radicals by homolysis can abstract a suitable species like a hydrogen atom or a halogen atom from a compound to generate a new radical. This ability of radicals to propagate by abstraction is a crucial feature of radical chain reactions.
Even though homolysis produces radicals, it is different from radical...
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Radical Reactivity: Intramolecular vs Intermolecular01:33

Radical Reactivity: Intramolecular vs Intermolecular

2.3K
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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Light-driven Molecular Motors on Surfaces for Single Molecular Imaging
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Introducing Stable Radicals into Molecular Machines.

Yuping Wang1, Marco Frasconi2, J Fraser Stoddart1

  • 1Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, United States.

ACS Central Science
|October 6, 2017
PubMed
Summary
This summary is machine-generated.

Stable organic radicals, like the bipyridinium radical cation (BIPY•+), are key to creating advanced molecular machines. Radical pairing interactions are crucial for synthesizing and enabling the function of these novel systems.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry
  • Materials Science

Background:

  • Stable organic radicals possess unique optical, electronic, and magnetic properties.
  • Developing artificial molecular machines that perform work using external energy is a significant challenge in chemistry.
  • Radical-pairing interactions offer a pathway to address this challenge by aiding synthesis and enabling multifunctional systems.

Purpose of the Study:

  • To highlight research on incorporating radical-pairing interactions into functional systems, using the radical cationic state of 1,1'-dialkyl-4,4'-bipyridinium (BIPY•+) as a model.
  • To demonstrate the application of these interactions in prototypical molecular switches and complex molecular machines.
  • To discuss current limitations and future research directions for BIPY•+-based molecular machines.

Main Methods:

  • Utilizing radical-pairing interactions for supramolecular assistance in molecular machine synthesis.
  • Designing and constructing molecular switches and machines incorporating BIPY•+ species.
  • Analyzing the properties and functions of radical-paired systems.

Main Results:

  • Demonstrated the successful integration of radical-pairing interactions in the design of molecular switches and machines.
  • Showcased the versatility of BIPY•+ in creating functional molecular systems.
  • Identified key limitations in current designs and proposed avenues for future development.

Conclusions:

  • Radical-pairing interactions are essential for advancing the field of molecular machines.
  • BIPY•+ serves as a valuable platform for developing sophisticated, functional molecular machines.
  • Further research is needed to overcome current limitations and unlock the full potential of these systems.