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Isolable photoreactive polysilyl radicals.

Gregory Molev1, Boris Tumanskii, Dennis Sheberla

  • 1Schulich Faculty of Chemistry and the Lise Meitner Minerva Center for Computational Quantum Chemistry, Technion-Israel Institute of Technology, Haifa 32000, Israel.

Journal of the American Chemical Society
|September 3, 2009
PubMed
Summary
This summary is machine-generated.

Stable silyl radicals were synthesized using a novel one-step method. These silicon radicals exhibit unique photochemical properties, with one type decaying into silane and disilene, while the other undergoes hydrogen abstraction upon irradiation.

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Area of Science:

  • Organosilicon Chemistry
  • Radical Chemistry
  • Photochemistry

Background:

  • Stable silyl radicals are crucial intermediates in silicon chemistry.
  • Previous methods for synthesizing silyl radicals were limited.
  • Understanding the reactivity and photochemistry of silyl radicals is essential for developing new synthetic routes.

Purpose of the Study:

  • To develop a general and efficient one-step method for synthesizing stable silyl radicals.
  • To characterize the structure and properties of newly synthesized silyl radicals.
  • To investigate the photochemical behavior and reaction mechanisms of these silyl radicals.

Main Methods:

  • Reaction of silyl substituted dichlorosilanes with lithiosilanes in hexane.
  • Isolation and full characterization of silyl radicals, including X-ray crystallography.
  • Photochemical irradiation experiments (λ > 400 nm) and DFT calculations.

Main Results:

  • A novel one-step synthesis exclusively yields stable silyl radicals.
  • Two silyl radicals, (t-Bu(2)MeSi)(2)HSi(t-Bu(2)MeSi)(2)Si* (1) and (t-Bu(2)MeSi)(3)Si* (2), were isolated and characterized.
  • Radical 1 undergoes photolytic decay to silane and disilene; Radical 2 shows photostability but abstracts hydrogen upon irradiation.
  • DFT calculations and irradiation data indicate SOMO-1 → SOMO excitation influences photoreactivity.

Conclusions:

  • The developed one-step method is a general approach for synthesizing diverse stable silyl radicals.
  • Silyl radicals exhibit distinct photochemical reactivity, influenced by their electronic structure.
  • Photoreactivity is linked to specific electronic excitations, enabling controlled chemical transformations.