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A Sn(IV) <i>meso</i>-tetra(4-methylthiolphenyl) N-confused porphyrin (<b>4-Sn</b>) complex was prepared to facilitate a comparison of the photophysicochemical and singlet oxygen photosensitiser properties of a series of Sn(IV) complexes of <i>meso</i>-4-methylthiolphenyl-substituted porphyrin, corrole, chlorin, and N-confused porphyrin. <b>4-Sn</b> has an unusually high singlet oxygen quantum (Φ_Δ) yield of 0.88, markedly higher than the Φ_Δ values of the other complexes in this series. A Thorlabs M660L4 LED (280 mW · cm⁻²) was used to study the photodynamic activity of <b>Sn-4</b> against the MCF-7 cancer cell line through irradiation at 660 nm for 30 min. The IC₅₀ value was calculated to be 1.4 (± 0.8) µM, markedly lower than the previously reported values for the rest of the series. Photodynamic antimicrobial activity was also determined against <i>Staphylococcus aureus</i> and <i>Escherichia coli</i>, and <b>4-Sn</b> was found to deactivate both Gram-(+) and Gram-(−) bacteria despite the absence of cationic charges on the ligand structure.