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-su bstituted diiminoisoindolines with XSiCl3 followed by quenching with an alc ohol YOH. Three synthetic routes for adding anchoring groups to the phthalo cyanines were explored: variation of the axial groups X and Y, or incorpora tion of vinyl groups around the periphery of the phthalocyanine ring. The l atter approach yielded silicon and copper phthalocyanines with eight termin al vinyl groups, which reacted cleanly with thioacetic acid/AIBN to give pr oducts with eight protected terminal thiols. (C) 1998 Elsevier Science Limi ted. All rights reserved.