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Electro-inductive effect: Electrodes as functional groups with tunable electronic properties.

Joon Heo1,2, Hojin Ahn1, Joonghee Won1,2

  • 1Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 34141, Republic of Korea.

Science (New York, N.Y.)
|October 9, 2020
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Summary
This summary is machine-generated.

We demonstrate voltage-controlled tuning of molecular properties on gold electrodes. This electrochemically controlled surface chemistry enables inhibition of ester hydrolysis and modulation of cross-coupling and amidation reactions.

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Area of Science:

  • Electrochemistry
  • Surface Chemistry
  • Organic Synthesis

Background:

  • Traditional organic synthesis relies on functional groups to tune reactivity.
  • Controlling molecular properties via external stimuli offers new synthetic avenues.

Purpose of the Study:

  • To investigate the electrochemical control of molecular properties on gold surfaces.
  • To demonstrate voltage-driven modulation of organic reactions immobilized on electrodes.

Main Methods:

  • Immobilization of thiol-containing molecules onto gold electrodes.
  • Application of varying voltages to tune molecular properties and reaction rates.
  • Monitoring of ester saponification, Suzuki-Miyaura coupling, and carboxylic acid amidation.

Main Results:

  • Mildly negative voltage (-0.25 V vs OCP) completely inhibited base-catalyzed benzoic ester saponification.
  • Applied voltage modulated the rate of Suzuki-Miyaura cross-coupling for immobilized arylhalide substrates.
  • A two-step carboxylic acid amidation benefited from voltage switching between reaction steps.

Conclusions:

  • Electrochemical control of immobilized molecules provides a tunable platform for organic reactions.
  • Voltage-induced property modulation offers a novel approach to reaction optimization and control.
  • This method presents an alternative to traditional functional group manipulation in organic synthesis.