The oxidation of octaethylporphyrin (OEP) using H2O2/H2SO4 was firstly described in 1927, but its outcome was misinterpreted. The products were correctly described as oxochlorins in 1964 and dioxochlorins in 1969, yet to date no structural proof was provided. We present here the first complete spectroscopic and structural characterization of free base octaethyloxochlorin and all dioxobacteriochlorin and dioxoisobacteriochlorin isomers, some of which form only in miniscule yields. The optical properties of some isomers are attractive for further study because of their NIR-absorption properties.

Old reaction, new insights: The structures of all regioisomers of oxo- and dioxochlorins

250th National Meeting (2015)

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