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Radical Reactivity: Nucleophilic Radicals

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Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For...
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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.
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Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

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Radicals adjacent to electron‐withdrawing groups are called electrophilic radicals. These radicals readily react with nucleophilic alkenes. For example, the malonate radical, in which the radical center is flanked by two electron‐withdrawing groups, reacts readily with butyl vinyl ether, which consists of an electron‐donating oxygen substituent. The reaction between electrophilic malonate radical and nucleophilic vinyl ether is favored because the radical has a...
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Radical Reactivity: Overview01:11

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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

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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:
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The oxidation of an organic compound in the presence of air or oxygen is called autoxidation. For example, cumene reacts with oxygen to form hydroperoxide. Autoxidation involves initiation, propagation, and termination steps. Many organic compounds are susceptible to autoxidation—especially ethers in the presence of oxygen, which form hydroperoxides. Even though this reaction is slow, old ether bottles contain small amounts of peroxide, which leads to laboratory explosions during ether...
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Oligorotaxane Radicals under Orders.

Yuping Wang1, Marco Frasconi1, Wei-Guang Liu2

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

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|May 11, 2016
PubMed
Summary
This summary is machine-generated.

Researchers developed positively charged foldameric oligorotaxanes using oligoviologens and cyclobis(paraquat-p-phenylene) rings. These mechanically interlocked molecules exhibit reversible folding and unfolding, mimicking muscle fiber actuation through electrochemical control.

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Area of Science:

  • Supramolecular Chemistry
  • Materials Science
  • Nanotechnology

Background:

  • Developing novel mechanically interlocked molecules (MIMs) is crucial for advanced functional materials.
  • Creating all-positive charge systems presents unique challenges in supramolecular assembly.
  • Foldameric structures offer tunable properties for molecular machines.

Purpose of the Study:

  • To report a strategy for constructing foldameric oligorotaxanes using exclusively positive components.
  • To investigate the self-assembly and electrochemical properties of these novel MIMs.
  • To explore the potential of these systems as molecular actuators.

Main Methods:

  • Synthesis of oligoviologen threads and cyclobis(paraquat-p-phenylene) (CBPQT(4+)) rings.
  • Threading of oligoviologens by CBPQT(4+)) rings under reducing conditions to form radical cation pairs.
  • Characterization using UV/vis/NIR spectroscopy and electrochemistry.
  • Stopper installation via Cu-free alkyne-azide cycloadditions to form stable oligorotaxanes.

Main Results:

  • Successful formation of foldameric oligorotaxanes with all-positive charge components.
  • Observation of secondary structure folding in reduced oligopseudorotaxanes due to radical cation pair formation.
  • Demonstration of electrochemically controlled reversible folding (contraction) and unfolding (expansion) of the oligorotaxanes.
  • The observed actuation mechanism is analogous to that of biological muscle fibers.

Conclusions:

  • A viable strategy for creating all-positive charge foldameric oligorotaxanes has been established.
  • These MIMs exhibit stimulus-responsive behavior, folding and unfolding based on redox state.
  • The reversible length changes suggest potential applications in molecular machines and artificial muscles.