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Stable Open-Shell Phosphorane Based on a Redox-Active Amidodiphenoxide Scaffold.

Allen J Pistner, Hye Won Moon1, Alexey Silakov

  • 1Department of Chemistry, Massachusetts Institute of Technology (MIT) , Cambridge, Massachusetts 02139, United States.

Inorganic Chemistry
|June 30, 2017
PubMed
Summary

Pentacoordinate phosphorus compounds with a redox-active ONO amidodiphenoxide scaffold were synthesized. The diphenylphosphorane derivative exhibits reversible oxidation and forms a delocalized radical cation, indicating fast electron transfer.

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Area of Science:

  • Organophosphorus Chemistry
  • Redox-Active Ligand Systems
  • Coordination Chemistry

Background:

  • Pentacoordinate phosphorus compounds are crucial in various chemical transformations.
  • Redox-active ligands offer tunable electronic properties for novel material design.
  • Understanding electron delocalization in radical species is key to designing advanced functional molecules.

Purpose of the Study:

  • To synthesize and characterize pentacoordinate phosphorus compounds featuring a redox-active ONO amidodiphenoxide scaffold.
  • To investigate the redox behavior and electronic properties of these novel phosphorus complexes.
  • To explore the nature of radical cation formation and electron delocalization within the ONO framework.

Main Methods:

  • Synthesis of dichloro- and diphenylphosphoranes.
  • Crystallographic characterization of the synthesized compounds.
  • Electrochemical analysis using cyclic voltammetry.
  • Chemical oxidation and characterization of the radical cation using electron paramagnetic resonance (EPR) spectroscopy and density functional theory (DFT) calculations.
  • Nuclear magnetic resonance (NMR) line-broadening experiments to study electron transfer kinetics.

Main Results:

  • Successful synthesis and structural characterization of dichloro- and diphenylphosphoranes incorporating the ONO scaffold.
  • Differential redox potentials observed: irreversible oxidation for the dichloro analogue and reversible oxidation for the diphenyl analogue.
  • Formation of a stable radical cation ([2·Ph2]•+) upon chemical oxidation, with delocalized spin density primarily on the ONO ligand framework.
  • Minimal structural changes between neutral and oxidized forms, consistent with rapid electron self-exchange.

Conclusions:

  • Pentacoordinate phosphorus compounds with redox-active ONO amidodiphenoxide ligands can be effectively synthesized.
  • The diphenylphosphorane derivative demonstrates tunable redox properties and facilitates the formation of a delocalized radical cation.
  • The ONO scaffold plays a crucial role in stabilizing the radical cation and enabling fast electron transfer processes.