Combinatorial reactions of two a-aminoketones and two diones in water (pH 7, 60 �C) with accompanying photooxidation afford a series of porphyrins distinguished by four classes of polarity: hydrophilic, indeterminate, amphiphilic, and hydrophobic. The reaction in the presence of lipid vesicles leads upon polarity-based self-sorting to porphyrin-containing vesicles that are photoactive, as demonstrated by the Krasnovsky reaction (a photosynthetic-like process). The spontaneous formation of photoactive protocells from acyclic reactants provides a model for the origin of proto-photosynthesis.

Photoactive protocells from acyclic reactants in a one-flask process

243rd National Meeting (2012)

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