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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 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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Radical Chain-Growth Polymerization: Chain Branching01:17

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The skeletal structure of polymers synthesized via radical polymerization is always branched. For example, the polymerization of ethylene by radical polymerization results in a low-density grade of polyethylene with a heavily branched skeletal structure. Here, the radical site abstracts hydrogen from the growing chain, and the radical site shifts from the end (a primary carbon center) to anywhere within the growing chain (a secondary carbon center). Consequently, the part of the chain from the...
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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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Radical Chain-Growth Polymerization: Mechanism01:09

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The radical chain-growth polymerization mechanism consists of three steps: initiation, propagation, and termination of polymerization. The polymerization initiates when a free radical generated from the radical initiator adds to the unsaturated bond in the monomer. The unpaired electron of the free radical and one π electron in the unsaturated bond creates a σ bond between the free radical and the monomer. As a result, the other π electron in the unsaturated bond converts this...
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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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Revealing Pathway Complexity and Helical Inversion in Supramolecular Assemblies Through Solvent-Induced Radical

Haotian Ma1, Xiaoxiao Cheng1, Gong Zhang1

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Advanced Science (Weinheim, Baden-Wurttemberg, Germany)
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Summary

Chiral triarylamine tris-amide monomers self-assemble into different nanostructures based on solvent choice. Solvent interactions control helical arrangement and excited-state chirality, offering new manipulation approaches.

Keywords:
helical inversionpathway complexityradicalssolvent–solute interactionsupramolecular assembly

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Area of Science:

  • Supramolecular chemistry
  • Materials science
  • Chiral assembly

Background:

  • Chiral triarylamine tris-amide (TATA) monomers are building blocks for complex supramolecular structures.
  • Understanding the factors influencing TATA monomer assembly is crucial for designing novel nanomaterials.

Purpose of the Study:

  • To investigate the influence of cosolvent systems on the supramolecular assembly pathway of TATA monomers.
  • To elucidate the role of solvent-induced radical and neutral species dynamics in dictating assembly outcomes.
  • To explore the relationship between assembly pathways, morphology, and excited-state chirality.

Main Methods:

  • Utilized cosolvent systems (1,2-dichloroethane with methylcyclohexane or hexane) to study TATA monomer assembly.
  • Analyzed the resulting supramolecular structures, including helical arrangement and morphology (nanobelts, nanofibers).
  • Investigated mechanistic pathways involving radical and neutral triarylamine species and their interaction with solvent structures.

Main Results:

  • Cosolvents dictate distinct assembly pathways: cooperative growth (M-helix, nanobelts) in DCE/MCH vs. isodesmic growth (P-helix, nanofibers) in DCE/HE.
  • The two assembly pathways lead to opposite excited-state chirality.
  • Radical neutralization in MCH significantly impacts pathway complexity, influencing helicity and morphology.

Conclusions:

  • Solvent composition critically controls chiral supramolecular assembly pathways and resulting nanostructures.
  • Radical species dynamics are key to understanding and manipulating assembly complexity and chirality.
  • Facile solvent-solute interactions offer a novel strategy for controlling chiral supramolecular assembly.