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When disubstituted benzenes undergo electrophilic substitution, the product distribution depends on the directing effect of both substituents. When the directing effects of both substituents reinforce each other, a single product is obtained. For example, bromination of p-nitrotoluene occurs ortho to the methyl group and meta to the nitro group, which is the same position, resulting in a single product. However, if the directing effects of the two groups oppose each other, the...
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Ferrocene-Containing Sterically Hindered Phosphonium Salts.

Vadim Ermolaev1, Tatiana Gerasimova2, Liliya Kadyrgulova3

  • 1Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, 8 Arbuzov St., Kazan 420088, Russia. ermolaewadim@gmail.com.

Molecules (Basel, Switzerland)
|October 28, 2018
PubMed
Summary

Researchers synthesized novel ferrocenyl phosphonium salts and studied their electrochemical properties. Structural modifications, like changing the anion, influence their redox behavior, suggesting potential for energy storage applications.

Keywords:
DFT calculationcyclic voltammetryferroceneferrocene-containing compoundsionic liquidsphosphonium salts

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Area of Science:

  • Electrochemistry
  • Organometallic Chemistry
  • Materials Science

Background:

  • Sterically hindered phosphonium salts are crucial in various chemical applications.
  • Ferrocene derivatives offer unique redox properties for advanced materials.
  • Understanding structure-property relationships is key for designing functional molecules.

Purpose of the Study:

  • To synthesize and characterize novel ferrocenyl-containing sterically hindered phosphonium salts.
  • To investigate the impact of structural variations on their electrochemical behavior.
  • To explore potential applications in energy storage devices.

Main Methods:

  • Synthesis of phosphonium salts based on di(tert-butyl)ferrocenylphosphine.
  • Electrochemical analysis using voltammetry.
  • Density Functional Theory (DFT) calculations.

Main Results:

  • Established correlations between salt structure and electrochemical properties.
  • Observed shifts in ferrocene/ferrocenium transition potentials with structural changes.
  • DFT revealed the influence of bromide anions on highest occupied molecular orbital (HOMO) energy and ion pair stability.

Conclusions:

  • Structural modifications, including alkyl chain length and anion type, allow fine-tuning of redox properties.
  • The bromide anion destabilizes ion pairs, facilitating oxidation.
  • These tailored phosphonium salts show promise for multicomponent batteries and capacitors.