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Synthesis of Polyynes Using Dicobalt Masking Groups.

Daniel R Kohn1, Przemyslaw Gawel1, Yaoyao Xiong1

  • 1Department of Chemistry, Chemistry Research Laboratory, University of Oxford , Oxford OX1 3TA, United Kingdom.

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|January 24, 2018
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Researchers developed a new method to synthesize long polyynes using a dicobalt tetracarbonyldiphenylphosphinomethane (Co2(CO)4dppm) complex. This "masked alkyne equivalent" allows for the creation of fragile polyynes with up to 20 carbon atoms under mild conditions.

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Organometallic Chemistry

Background:

  • Polyynes, chains of sp-hybridized carbon atoms, are challenging to synthesize and stabilize.
  • The dicobalt tetracarbonyldiphenylphosphinomethane (Co2(CO)4dppm) complex has been explored as a protecting group for alkynes.

Purpose of the Study:

  • To develop a mild method for preparing extended, triisopropylsilyl end-capped polyynes.
  • To investigate the influence of the Co2(CO)4dppm moiety on polyyne properties.

Main Methods:

  • Synthesis of tetracobalt complexes containing polyyne precursors.
  • Mild deprotection using elemental iodine at room temperature.
  • Characterization using NMR and IR spectroscopy, density functional theory (DFT) calculations, and X-ray crystallography.

Main Results:

  • Successful preparation of fragile polyynes with up to 20 contiguous sp-hybridized carbon atoms.
  • The Co2(CO)4dppm moiety exerts significant geometric and steric effects but minimal electronic effects on the polyyne.
  • Observed minor side reaction of "alkyne hopping" during copper-catalyzed Eglinton coupling.

Conclusions:

  • The Co2(CO)4dppm complex serves as an effective "masked alkyne equivalent" for synthesizing long polyynes.
  • The developed method enables access to previously inaccessible polyyne structures.
  • Understanding the effects of the protecting group is crucial for polyyne synthesis and application.