Quicker Way to Triphenylamine Derivatives

  • Author: ChemViews
  • Published Date: 17 April 2011
  • Source / Publisher: European Journal of Organic Chemistry/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
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Dye-sensitized solar cells that convert sunlight into electricity often use triphenylamine (TPA) derivatives due to their high light-to-electrical energy-conversion efficiencies. There are numerous ways to make TPA derivatives, but most require toxic substrates, harsh conditions, and/or long reaction times.

Jieshan Qiu and colleagues, Dalian University of Technology, China, have reported a synthesis for the construction of 4-substituted TPA derivatives that is fast, ligand-free, and can be performed in air. They use a palladium(II)-catalyzed Suzuki reaction to couple aryl halides with [4-(diphenylamino)phenyl]boronic acid. The coupling could be achieved in 98 % yield in less than five minutes with an isopropanol/water solvent mix at room temperature. A wide range of substrates, including aryl bromides and heteroaryl halides, could be used, giving a simple and inexpensive route to TPA derivatives for improved solar cells.

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