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Expanded Porphyrins
Cyclo[n]pyrrole

 
    The development of novel expanded porphyrins and expanded Schiff base complexes lies at the heart of research in the Sessler group.  While a number of the current research projects are aimed at the applications of these macrocycles, further funtionalization and development of new macrocycles remains a primary goal in our group.


 
Cyclo[8]pyrrole

Cyclo[8]pyrrole (2; [30]octaphyrin(0.0.0.0.0.0.0.0)) has replaced all four mesocarbon bridges with four additional pyrrolic rings.  Therefore, 2 possesses an extended 30-p-electron periphery that is aromatic in the Hückel (4n+2) p electron sense.

A relatively straightforward 1 pot synthesis of cyclo[8]pyrrole has been recently desribed.  The ease of this cyclicization suggests that a number of similar macrocycles could be made.

Seidel, D.; Lynch V.; Sessler, J. L. Angew. Chem. Int. Ed. 2002, 41(8), 1422-1425.

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