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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 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 Formation: Addition00:47

Radical Formation: Addition

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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.
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Deactivation Processes: Jablonski Diagram01:25

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Luminescence, the emission of light by a substance that has absorbed energy, is a process that involves the interaction of molecules with light. The energy-level diagram, or Jablonski diagram, is a graphical representation of these interactions, illustrating the various states and transitions a molecule can undergo. In a typical Jablonski diagram, the lowest horizontal line represents the ground-state energy of the molecule, which is usually a singlet state. This state represents the energies...
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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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Photochemical Electrocyclic Reactions: Stereochemistry01:26

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The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
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Updated: May 16, 2025

Single-Molecule Förster Resonance Energy Transfer Methods for Real-Time Investigation of the Holliday Junction Resolution by GEN1
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Reversible Quinoid-Diradical Inter-Conversion in Single-Molecule Junctions.

Ming Chen1, Yunjiao Peng2, Junrui Zhang1

  • 1School of Chemistry and Chemical Engineering, Zhejiang Sci-Tech University, Hangzhou, Zhejiang, 310018, China.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|March 31, 2025
PubMed
Summary
This summary is machine-generated.

Researchers developed a novel molecular wire that acts as a reversible switch. This organic molecule exhibits a significant change in electrical conductance, paving the way for advanced molecular switching devices.

Keywords:
acid‐base manipulationquinoid‐diradical inter‐conversionreversibilitysingle‐molecule electronics

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Area of Science:

  • Molecular electronics
  • Organic electronics
  • Supramolecular chemistry

Background:

  • Understanding redox states in organic molecules is crucial for developing molecular switches.
  • Oligo-aniline derivatives offer potential for tunable electronic properties.

Purpose of the Study:

  • To design and synthesize an oligo-aniline derived quinoidal molecular wire.
  • To investigate its reversible redox state inter-conversion and single-molecule charge transport properties.
  • To elucidate the mechanism of quinoid-diradical transformation.

Main Methods:

  • Synthesis of an oligo-aniline derived quinoidal molecular wire.
  • Optical measurements and Electron Paramagnetic Resonance (EPR) spectroscopy for redox state analysis.
  • Scanning tunneling microscopy break junction (STM-BJ) technique for single-molecule charge transport measurements.
  • Theoretical analyses for mechanistic elucidation.

Main Results:

  • The synthesized molecular wire (O-ANI) demonstrates reversible switching between quinoid and protonated diradical states.
  • EPR experiments confirmed the formation of radical species upon protonation.
  • Single-molecule conductance measurements revealed a ≈ 6.5-fold conductance variation via acid/base adjustments.
  • Theoretical studies provided insights into the quinoid-diradical inter-conversion mechanism.

Conclusions:

  • The O-ANI molecular wire functions as a reversible molecular switch with significant conductance modulation.
  • The study enhances understanding of reversible quinoid-diradical inter-conversion at the single-molecule level.
  • Findings offer new strategies for developing advanced molecular switching materials and devices.