Synthesis and characterization of functionalized silicon phthalocyanines for fabrication of self-assembled monolayers

Novel octasubstituted phthalocyanine derivatives XYSiPc(OR)8 (X=alkyl, Y=alkoxy, R=alkane or alkene) were synthesized by reaction of alkoxy-substituted diiminoisoindolines with XSiCl3 followed by quenching with an alcohol YOH. Three synthetic routes for adding anchoring groups to the phthalocyanines were explored: variation of the axial groups X and Y, or incorporation of vinyl groups around the periphery of the phthalocyanine ring. The latter approach yielded silicon and copper phthalocyanines with eight terminal vinyl groups, which reacted cleanly with thioacetic acid/AIBN to give products with eight protected terminal thiols.