5,10,15-Tris(4-sulfonatophenyl)corrole

  • ChemPubSoc Europe Logo
  • Author: European Journal of Organic Chemistry
  • Published Date: 16 October 2019
  • Source / Publisher: European Journal of Organic Chemistry/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
thumbnail image: 5,10,15-Tris(4-sulfonatophenyl)corrole

Related Societies

Porphyrins and similar compounds have been intensively studied, both to study their functions in natural systems and to use their chemical properties. Corrole, for example, has applications in catalysis, sensors, and medicine.


The controlled aggregation of the corrole macrocycles is a key step for the preparation of functional corrole-based materials. In the porphyrin family, one of the most studied macrocycles is the commercially available 5,10,10,20-tetrasulfonatophenylporphyrin, which in acidic aqueous solutions spontaneously forms ordered aggregates. Unfortunately, the synthetic strategy used for the sulfonation of porphyrins cannot be applied to the corrole ring.


Roberto Paolesse, University of Rome "Tor Vergata", Italy, and colleagues have developed two synthetic routes to obtain the water-soluble 5,10,15-tris(4-sulfonatophenyl)corrole (pictured). The first approach uses a chlorosulfonation of the phosphorus complex of 5,10,15‐tris(4‐trimethylsilylphenyl)corrole. It provides only low yields of the desired compound in the form of its phosphorus complex. The second approach uses a reaction between pyrrole and 4‐chlorosulfonyl benzaldehyde, followed by hydrolysis of the obtained chlorosulfonyl-substituted corrole, to give the desired product in 10 % yield.


Different from the analogous porphyrin, this water-soluble corrole does not aggregate in acidic solutions. Instead, it is present as a monomeric zwitterionic species even at pH = 2. This result may be attributed to the lower symmetry of the corrole ring, which reduces the efficiency of molecular packing. However, the lack of aggregation could allow the use of this corrole for the preparation of hybrid nanostructured systems, where this macrocycle is conjugated with positively charged porphyrinoids. In future work, the researchers want to prepare these hybrid aggregates and explore their performance as sensing materials.


 

Article Views: 749

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

Bookmark and Share

If you would like to reuse any content, in print or online, from ChemistryViews.org, please contact us first for permission. more


CONNECT:

ChemistryViews.org on Facebook

ChemistryViews.org on Twitter ChemistryViews.org on YouTube ChemistryViews.org on LinkedIn Sign up for our free newsletter


A product of ChemPubSoc Europe (16 European Chemical Societies)and Wiley-VCH