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Peripherally Silylated Porphyrins.

Kenichi Kato1, Keisuke Fujimoto1, Hideki Yorimitsu2,3

  • 1Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku Kyoto, 606-8502 (Japan), Fax: (+81) 75-753-3970.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|September 11, 2015
PubMed
Summary

Researchers synthesized novel silyl-substituted porphyrins, exploring the reactivity and effects of meso- and β-silyl groups. Disilane-bridged porphyrin dimers, including a nickel(II) complex, were successfully created and characterized.

Keywords:
lithiationporphyrinporphyrin dimersilylationsubstituent effects

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Area of Science:

  • Organic Chemistry
  • Organometallic Chemistry
  • Materials Science

Background:

  • Porphyrins are versatile macrocyclic compounds with applications in catalysis and materials.
  • Direct functionalization of porphyrin peripheries remains a synthetic challenge.
  • Silyl groups offer unique electronic and steric properties for molecular design.

Purpose of the Study:

  • To develop a synthetic route for directly silyl-substituted porphyrins.
  • To investigate the stability and substituent effects of meso- and β-silyl groups.
  • To synthesize and characterize novel silyl-bridged porphyrin dimers.

Main Methods:

  • Peripheral lithiation of porphyrins followed by electrophilic silylation.
  • Reaction of lithiated porphyrins with 1,2-dichlorodisilane for bridging.
  • X-ray crystallographic analysis of disilane-bridged nickel(II)-porphyrin dimer.
  • Protodesilylation and denickelation reactions.

Main Results:

  • First synthesis of directly meso- and β-silyl-substituted porphyrins achieved.
  • Meso-silyl groups showed greater substituent effects and facile protodesilylation.
  • β-silyl groups were stable under standard purification conditions.
  • Synthesis of β-to-β disilane-bridged porphyrin dimers, including a Ni(II) dimer with a steplike structure.
  • Successful denickelation of β-silylporphyrins to freebase porphyrins.

Conclusions:

  • Direct silylation provides a viable pathway to functionalized porphyrins.
  • The position of the silyl group significantly influences its reactivity and electronic impact.
  • Disilane-bridged porphyrin dimers exhibit unique structural features potentially enabling interporphyrinic interactions.
  • The developed methods offer new avenues for porphyrin-based material synthesis.