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A novel series of silicon(IV) phthalocyanines with one or two axial acetal-protected galactose substituent(s) have been prepared by typical substitution reactions. The compounds exhibit a high photodynamic activity against HepG2 human hepatocarcinoma cells with IC50 values down to 0.10 μM.

A novel silicon(IV) phthalocyanine with two axial poly(sebacic anhydride) chains has been synthesized by melt condensation of silicon phthalocyanine dihydrox- ide and oligo(sebacic anhydride). The polymer has been spectroscopically characterized and its molecular weights have been determined by gel permeation chromatography (GPC) and 1 H NMR spectroscopy. Nanoparticles with an intensity-average apparent hydrodynamic radius of 65 1 nm have been prepared from this polymer via a microphase inversion method with sodium dodecyl sulfate as the surfactant. The spherical nanoparticles contain loosely aggregated polymer chains, trapping about 90% of the water. On treatment with NaOH, these nanoparticles undergo degradation that has been monitored by laser light scattering and fluorescence spectroscopy. Because of the axial substitution, the change in the aggregation state of the phthalocyanine core of this polymer during nanoparticle formation and degradation is relatively small com- pared with that of the zinc(II) phthalocyanine analogue reported earlier, in which poly(sebacic anhydride) chains are linked to the periphery of the phthalocyanine ring.

A new series of phthalocyanine-containing biodegradable poly(e-caprolactone)s have been synthesized by ring-opening polymerization of e-caprolactone and/or 5-ethylene ketal e-caprolactone using silicon phthalocyanine dihydroxide as the initiator and tin(II) 2-ethylhexanoate as the catalyst. The polymers have been spectroscopically characterized, and their molecular weights have been determined by gel permeation chromatography (GPC). All the polymers exhibit typical electronic absorption and fluorescence characteristics for nonaggregated phthalocyanines. The singlet oxygen quantum yields of selected polymers have been determined and found to be slightly lower than that of unsubstituted zinc(II) phthalocyanine in N,N-dimethylformamide (DMF). Nanoparticles with an average hydrodynamic radius 〈Rh〉 of ∼87 nm have been prepared from the homo-poly(e-caprolactone) 3a and 3b (bulk) via a microphase inversion method. The ketal-containing analogues 5−7 are able to form nanoparticles with a smaller dimension (〈Rh〉 = ...