Alternate Route to 27-Thiasapphyrins

  • Author: Asian Journal of Organic Chemistry
  • Published Date: 09 April 2014
  • Source / Publisher: Angewandte Chemie International Edition/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
thumbnail image: Alternate Route to 27-Thiasapphyrins

Sapphyrins were the first stable expanded porphyrins reported. They are pentapyrrolic 22π-electron aromatic macrocycles that contain one direct link and four bridging methine groups between the five pyrrolic rings. These macrocycles are versatile anion binding agents and also have rich porphyrin-like coordination chemistry. Sapphyrins are usually synthesized by using 2,2'-bipyrrole, which contains a pyrrole–pyrrole bond, as the key precursor but this compound is not readily available. Therefore, Mangalampalli Ravikanth and co-workers, Indian Institute of Technology, Bombay, have used an alternate strategy to prepare meso-tetraaryl 27-thiasapphyrins from readily available precursors.

The 27-thiasapphyrins were prepared by acid-catalyzed condensation of meso-aryl dipyrromethane and 2,5-bis(p-arylhydroxymethyl)thiophene (thiophene diol) under mild, acid-catalyzed conditions. Unlike the earlier strategies, in which 2,2-bipyrrole was the key precursor, in this strategy, the pyrrole–pyrrole bond was generated by oxidative coupling of meso-aryl dipyrromethane and thiophene diol, which are readily available precursors. These macrocycles have the potential to act as ligands to form metal complexes.

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