Abstract
A rigid hexadecamethyl substituted phthalocyanine (Pc*) silicon(IV) dichloride was synthesized by template cyclization of corresponding 1,3-diiminoisoindoline derivative with SiCl4. Attempts to prepare the same compound by insertion of HSiCl3 into preformed H2Pc* in the presence of bases were unsuccessful. Exchange of the axial chloride ligands with trimethylsiloxy groups made the molecular complex Pc*Si(OTMS)2 very soluble and non-aggregating, as shown by UV–Vis experiments. The effect of such peripheral alkyl substitution on the singlet oxygen quantum yield of the Pc*Si(OTMS)2 complex was determined and found to be 0.28; significantly lower than that for unsubstituted parent PcSi(OTMS)2. The merit of improving solubility over reduced singlet oxygen quantum yields is discussed.
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