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Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
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Ambient stable zwitterionic perylene bisimide-centered radical.

David Schmidt1, David Bialas, Frank Würthner

  • 1Universität Würzburg, Institut für Organische Chemie & Center for Nanosystems Chemistry, Am Hubland, 97074 Würzburg (Germany).

Angewandte Chemie (International Ed. in English)
|November 14, 2014
PubMed
Summary

Researchers synthesized a stable zwitterionic radical from a tetrachloro-substituted perylene-3,4:9,10-tetracarboxylic acid bisimide (PBI) and an N-heterocyclic carbene. This novel PBI radical is fully characterized and electrochemically reversible.

Keywords:
N-heterocyclic carbenesdyesperylene bisimidespigmentsradicals

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Perylene-3,4:9,10-tetracarboxylic acid bisimides (PBIs) are versatile organic molecules with tunable electronic properties.
  • Stable radical species are of interest for applications in organic electronics and catalysis.
  • Introducing substituents onto the PBI core can significantly alter their chemical and physical characteristics.

Purpose of the Study:

  • To synthesize and characterize a novel zwitterionic radical based on a tetrachloro-substituted PBI.
  • To investigate the stability and electrochemical properties of the newly formed radical species.
  • To explore the potential for reversible redox transformations of the zwitterionic radical.

Main Methods:

  • Reaction of tetrachloro-substituted PBI (PBI-Cl4) with N-heterocyclic carbene (1,3-di-iso-propyl-imidazolin-2-ylidene, (iPr2Im)).
  • Isolation and characterization of the zwitterionic radical using spectroscopic methods (e.g., NMR, EPR, UV-Vis).
  • Single crystal X-ray diffraction for structural elucidation.
  • Electrochemical studies (e.g., cyclic voltammetry) to determine redox behavior.

Main Results:

  • Successful synthesis of an ambient stable zwitterionic radical by introducing a cationic imidazolium substituent onto the PBI core.
  • Comprehensive characterization confirmed the unprecedented PBI-centered radical structure.
  • Redox studies demonstrated reversible transfer between the zwitterionic radical, its corresponding anion, and cation on a preparative scale.

Conclusions:

  • The introduction of an N-heterocyclic carbene substituent enables the formation of a stable zwitterionic PBI radical.
  • This novel radical exhibits remarkable stability and is amenable to full structural and spectroscopic characterization.
  • The reversible redox behavior of the zwitterionic radical opens avenues for its application in redox-active materials and devices.