Functionalization of the Corrole Ring: A Neverending Game

Monday, 25 May 2015: 10:20
Lake Erie (Hilton Chicago)
R. Paolesse, S. Nardis, D. Monti, F. Mandoj, G. Pomarico, M. L. Naitana, C. Di Natale, and M. Stefanelli (University of Rome Tor Vergata)
Corrole has been one of the first porphyrinoids reported in the literature, but only in the last few years it has been observed an impressive boost in corrole researches, because it has shown some peculiar properties, different from those of the corresponding porphyrins, which are promising for practical applications.

From this point of view, it has been important to study the possible synthetic modifications of the corrole framework, with the aim to tune the properties of the resulting macrocycle to the corresponding application.

Although the impressive progress of the corrole preprative chemistry, the functionalization of this macrocycle  is still a challenging research area.

We have contributed to this area by studying the definition of synthetic protocols for the insertion of different substituents, both into the meso and b-positions of the macrocycle, with the aim of building more complex structures.

In these reaction, corrole has demonstrated a peculiar regioselectivity, with the substituents introduced in the directly linked pyrroles A and D. However we have recently observed that the substitution pattern can be modulated by the different substituents introduced in the peripheral positions.

In the present work we summarise our recent achievements in the functionalization of the corrole ring.