Porphyrins and derivatives are compounds of high interest due to their various uses such as light-harvesting, catalysis, and as biological models. However, the use of porphyrins has been held back because their synthesis usually results in low yields and requires a high-dilution reaction medium. This contributes to a very high-cost and environmentally taxing synthesis. We have previously shown that tetra-meso-substituted porphyrins are attainable using mechanochemistry. In this way solvent is eliminated, making the synthesis process greener and more cost-friendly. The compounds we aim to synthesize here are relevant biological model compounds. Porphine is the parent structure of all porphyrins and bis-pocket porphyrin is used as a model of heme in hemoglobin. Both porphyrins are currently synthesized in low yields (porphine less than 10%; bis-pocket porphyrin 1%) and using large amounts of solvent. We will present mechanochemical protocols for the synthesis of both compounds with characterizations using ultraviolet spectroscopy and proton nuclear magnetic resonance. Our synthesis of both porphyrins will be compared to those in literature using EcoScale as a green chemistry metric.

Mechanochemical synthesis of porphine and bis-pocket porphyrin

253rd National Meeting (2017)

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