Carbaporphyrinoid systems with one or more carbon atoms within a porphyrin-like cavity have been widely studied over the last twenty years. For instance, introduction of a benzene ring in place of one of the pyrrolic subunits affords benziporphyrins which readily yield organometallic derivatives under mild conditions. In principle, this synthetic approach can be used to introduce larger polycyclic aromatic hydrocarbon (PAH) subunits, although to date only naphthalene-containing analogues have been reported. In this study, the first example of a pyrene-containing porphyrinoid 1 has been synthesized by reacting pyrene dialdehyde 2 with a tripyrrane 3 in the presence of TFA, followed by oxidation with DDQ. This system does not possess macrocyclic aromaticity but is quite stable and reacts with palladium(II) acetate to give a stable palladium(II) derivative.

Synthesis of a PAH-porphyrin hybrid

251st National Meeting (2016)

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