Selective oxidative synthesis of meso-beta fused porphyrin dimers

Authors: Brennan, B.J., Arero, J., Liddell, P.A., Moore, T.A., Moore, A.L., and Gust, D.
Title: Selective oxidative synthesis of meso-beta fused porphyrin dimers
Source: Journal of Porphyrins and Phthalocyanines
Year: 2013
Volume: 17
Pages: 247-251


An efficient route to meso-β doubly connected fused porphyrin dimers was developed. Synthesis of the dimers incorporated two successive C-C bond-forming steps selectively coupling unsubstituted meso- and β- positions. Using Cu(BF4)2 as an oxidant in nitromethane solvent, the radical coupling of Cu(II)-porphyrins occurred in high yield and without side products, allowing chromatography-free purification. Efficient demetalation of the product yielded free-base derivatives and the possibility to incorporate other metals into the macrocycles. The absorption and electrochemical properties vary with the inserted metal, showing broad UV-Visible-NIR absorption and multiple oneelectron oxidations/reductions in a relatively narrow electrochemical window

Date of online publication: Thu, 2013-03-21
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