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Easy Demetalation of Porphyrins
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A simple, mild, methodology for the transformation of nickel porphyrins to the corresponding free-base porphyrins
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Nickel porphyrins are among the most commonly used building blocks for the construction of porphyrin-based architectures, as the diamagnetic nickel allows the ready characterization by NMR spectroscopy. However, nickel-based porphyrins are not useful for photophysical investigations as their photoexcited states decay to the ground state in a matter of picoseconds.
Atsuhiro Osuka and his group, Kyoto University, Japan, have found that treatment of nickel porphyrins with the Grignard reagent 4-methylphenylmagnesium bromide in specific solvents, results in smooth transmetalation of magnesium for nickel. The magnesium can then be removed under mildly acidic conditions to afford the free-base porphyrin.
This two-step methodology can also be applied to porphyrins complexed with other metals. For example, zinc, copper, and silver porphyrins also underwent a Grignard reaction to give the corresponding magnesium porphyrins, but unfortunately this methodology is not applicable to cobalt and palladium. Nevertheless, the demetalation of a variety of metal porphyrins, which is normally achieved only in very strongly acidic conditions, can now be performed much more easily.
Demetalation of Metal Porphyrins via Magnesium Porphyrins by Reaction with Grignard Reagent,
K. Murakami, Y. Yamamoto, H. Yorimitsu, A. Osuka,
Chem. Eur. J. 2013.
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