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.


Article Views: 3064

Sign in Area

Please sign in below

Additional Sign In options

Please note that to comment on an article you must be registered and logged in.
Registration is for free, you may already be registered to receive, e.g., the newsletter. When you register on this website, please ensure you view our terms and conditions. All comments are subject to moderation.

Article Comments - To add a comment please sign in

If you would like to reuse any content, in print or online, from ChemistryViews.org, please contact us first for permission and consult our permission guidance prior to making your request

Follow on Facebook Follow on Twitter Follow on YouTube Follow on LinkedIn Follow on Instagram RSS Sign up for newsletters

Magazine of Chemistry Europe (16 European Chemical Societies) published by Wiley-VCH