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Halogenation of Alkenes02:46

Halogenation of Alkenes

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Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
18.0K
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

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Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
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Related Experiment Video

Updated: Dec 8, 2025

Harvesting Solar Energy by Means of Charge-Separating Nanocrystals and Their Solids
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Harvesting Solar Energy by Means of Charge-Separating Nanocrystals and Their Solids

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Multi-carrier processes in halogenated Si nanocrystals.

N V Derbenyova1, V A Burdov1

  • 1Lobachevsky State University of Nizhny Novgorod, 23 Gagarin Avenue, 603950 Nizhny Novgorod, Russian Federation.

The Journal of Chemical Physics
|September 23, 2020
PubMed
Summary
This summary is machine-generated.

Bromine passivation significantly alters silicon nanocrystal electronic structure and multi-carrier processes more than chlorine. This effect is linked to stronger structural changes from bromine, impacting Auger recombination and multiple exciton generation rates.

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Area of Science:

  • Materials Science
  • Quantum Chemistry
  • Nanotechnology

Background:

  • Silicon nanocrystals are promising for optoelectronic applications.
  • Passivation is crucial for controlling their electronic properties.
  • Auger recombination and multiple exciton generation impact device efficiency.

Purpose of the Study:

  • To theoretically investigate the impact of Cl and Br passivation on silicon nanocrystals.
  • To analyze the effects on Auger recombination and multiple exciton generation.
  • To compare the influence of different passivating elements on electronic structure and process rates.

Main Methods:

  • Theoretical study using time-dependent density functional theory (TD-DFT).
  • Calculation of electronic structure and transition rates for Si317X172 nanocrystals (X=Cl, Br).
  • Comparison with hydrogen-passivated silicon nanocrystals.

Main Results:

  • Bromine passivation causes greater electronic structure and rate changes than chlorine passivation.
  • Stronger structural perturbations by bromine atoms are responsible for its larger effect.
  • Electron-hole asymmetry observed in multi-carrier processes for Br-passivated nanocrystals.
  • Chlorine passivation shows a weaker influence on these processes.

Conclusions:

  • Passivation element choice significantly impacts silicon nanocrystal performance.
  • Bromine's structural effects dominate its electronic influence on multi-carrier processes.
  • Understanding these effects is key for designing efficient silicon-based optoelectronic devices.