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Redox-Switchable Complexes Based on Nanographene-NHCs.

César Ruiz-Zambrana1, Rajeev K Dubey2, Macarena Poyatos1

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Chemistry (Weinheim an Der Bergstrasse, Germany)
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Summary

New rhodium and iridium catalysts featuring a perylene-diimide-pyrene moiety show redox-switchable behavior. Their catalytic activity in cycloaddition reactions can be turned on and off by electrochemical reduction.

Keywords:
N-heterocyclic carbenecycloadditionmechanismnanographeneredox-switchable

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Area of Science:

  • Organometallic Chemistry
  • Supramolecular Chemistry
  • Electrochemistry

Background:

  • N-heterocyclic carbenes (NHCs) are versatile ligands in organometallic chemistry.
  • Perylene diimides (PDIs) are known for their electronic and photophysical properties.
  • Combining NHCs with PDI moieties offers opportunities for novel functional materials and catalysts.

Purpose of the Study:

  • To synthesize and characterize novel rhodium and iridium complexes bearing a perylene-diimide-pyrene functionalized NHC ligand.
  • To investigate the electrochemical properties and redox behavior of these new metal complexes.
  • To evaluate the catalytic performance of the rhodium complex in a [3+2] cycloaddition reaction and explore its redox-switchable potential.

Main Methods:

  • Synthesis of rhodium and iridium complexes with the functionalized NHC ligand.
  • Electrochemical studies (cyclic voltammetry) to determine redox potentials.
  • Infrared spectroelectrochemistry to probe electronic changes upon reduction.
  • Catalytic testing of the rhodium complex in the [3+2] cycloaddition of diphenylcyclopropenone and methylphenylacetylene.

Main Results:

  • The synthesized rhodium and iridium complexes successfully incorporated the perylene-diimide-pyrene functionalized NHC ligand.
  • Electrochemical studies demonstrated two successive one-electron reduction events, attributed to the PDI moiety.
  • Infrared spectroelectrochemistry confirmed an increased electron-donating character of the ligand upon reduction.
  • The rhodium complex exhibited redox-switchable catalytic activity, with suppressed activity in its reduced state.

Conclusions:

  • Novel NHC-metal complexes with redox-active PDI units have been successfully synthesized.
  • The electronic properties of the NHC ligand can be tuned via electrochemical reduction.
  • The rhodium complex demonstrates potential as a redox-switchable catalyst for cycloaddition reactions.