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Related Concept Videos

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: Homolysis00:54

Radical Formation: Homolysis

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A bond is formed between two atoms by sharing two electrons. When this bond is broken by supplying sufficient energy, either two electrons can be taken up by one atom forming ions by the cleavage called heterolysis, or the two electrons are shared by two atoms, with one each creating radicals by the cleavage called homolysis.
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Radical Formation: Abstraction00:47

Radical Formation: Abstraction

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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 Chain-Growth Polymerization: Chain Branching01:17

Radical Chain-Growth Polymerization: Chain Branching

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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 Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

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Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...
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Hydrogen Migration-Triggered Diradicaloid Singlet-Fission Switch.

Qing Li1,2,3, Yu-He Kan1,2, Hong-Liang Xu1

  • 1Institute of Functional Material Chemistry, National and Local United Engineering Laboratory for Power Batteries, Faculty of Chemistry, Northeast Normal University, Changchun 130024, P. R. China.

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|June 11, 2020
PubMed
Summary
This summary is machine-generated.

We designed a singlet-fission (SF) switch using hydrogen tautomers in tetraazatetracenes. This method enhances diradical character and lowers energy levels, predicting over 120% SF efficiency for electronic devices.

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Area of Science:

  • Theoretical chemistry
  • Materials science
  • Photovoltaics

Background:

  • Singlet fission (SF) is a process where one high-energy singlet exciton splits into two lower-energy triplet excitons.
  • Developing efficient SF materials is crucial for advanced electronic devices, particularly in photovoltaics.
  • Hydrogen tautomerism offers a potential pathway for tuning electronic properties in organic molecules.

Purpose of the Study:

  • To theoretically design a novel singlet-fission (SF) interconversion mechanism using hydrogen tautomers.
  • To explore the potential of these systems as switches in SF-based electronic devices.
  • To establish design rules for achieving efficient SF through hydrogen migration.

Main Methods:

  • Theoretical design of π-electron conjugation strategy.
  • Utilizing single-hydrogen migration in pyrazine-fused tetraazatetracenes.
  • Analyzing diradical character and excited state energy levels (S0 and T1).

Main Results:

  • A strategy based on single-hydrogen migration was developed to introduce diradical character.
  • Low-lying E(T1) levels were achieved, crucial for efficient SF.
  • Predicted SF efficiency is expected to exceed 120% in the proposed tetraazatene systems.
  • A rule of thumb for SF design emerged, linking hydrogen migration to electron localization and π-conjugation.

Conclusions:

  • The proposed hydrogen tautomer design is effective for creating diradicaloid SF switches.
  • Single-hydrogen migration is key for localized electrons in the S0 state and broad π-conjugation in the T1 state.
  • This research provides a valuable framework for designing future SF materials for photovoltaic applications.