The water-soluble tin(IV) tetrakis(2-N-hydroxyethyl-4-pyridinium)porphyrin 1 photocatalyst was synthesized in good yield and its structure determined by single crystal X-ray crystallography. Electrochemical measurements on tin(IV) porphyrin 1 reveal a range of complex redox processes that are highly dependent on the pH and electrode used. The cathodic processes at ca. -0.6 to -0.8 V were assigned to electrochemical processes on the pyridyl moiety following differential pulse voltammetry and spectroelectrochemical investigation into the electrochemical properties of tin(IV) porphyrin. Photocatalytic experiment on tin(IV) porphyrin 1 under anaerobic conditions using triethanolamine (TEAO) as a sacrifical donor reveal a phlorin species as the main product which rapidly disappears upon exposure to oxygen. These results suggest that tin(IV) porphyrin π-radical anion is perhaps not the species responsible for the apparent ability tin(IV) porphyrins to photocatalytically reduce various substrates, including water to hydrogen.
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