Heck Synthesis of New Organosilicon Oligo(arylenevinylenes)

Two alternative synthetic approaches to new silicon-containing oligo(arylenevinylenes), 1,4-bis-{(E)-2-[4-(trimethylsilyl)phenyl]ethenyl}benzene and 9,10-bis{(E)-2-[4-(trimethylsilyl)phenyl]ethenyl}anthracene via Heck reactions of trimethyl(4-vinylphenyl)silane with the corresponding dibromoarenes and of (4-bromophenyl)trimethylsilane with the corresponding divinylarenes were studied. The reaction of 9,10-divinylanthracene with (4-bromophenyl)trimethylsilane was found to be accompanied by elimination of one trimethylsilyl group.