The acid-base, spectroscopic, photophysical and liposome-binding properties of the recently synthesized free base, 29H,31H,1,4,8,11,15,18,22,25-octafluoro-2,3,9,10,16,17,23, 24-octakisperfluoro(isopropyl) phthalocyanine, F₆₄PcH₂, are reported. The perfluoroalkylation of the phthalocyanine core renders the hydrogen atoms acidic, with a pK_a = 6. The F₆₄Pc⁻² dianion is detected already at pH 3, by singular-value decomposition analysis of electronic spectra. F₆₄Pc⁻² generates ¹O₂ with quantum yields Φ_Δ = 0.252 (in MeOH) and 0.019 in liposomes. Metallation of the Pc macrocycle to yield F₆₄PcZn increases Φ_Δ to 0.606 and 0.126 in MeOH and liposomes, respectively. Surprisingly, F₆₄Pc⁻² (but not F₆₄PcH₂ or F₆₄PcZn) binds strongly to liposomes, with a binding constant K_b = 25 (mg/mL)⁻¹. The fully protonated F₆₄PcH₂, but not the zwitterionic F₆₄Pc⁻², might favor hydrogen bonding, thus reducing its lipophilicity. Similarly, the Lewis acidity of Zn in F₆₄PcZn, and thus its ability to bind water within a hydrophobic perfluoroalkyl pocket, is significantly enhanced by the fluorinated substituents.