A series of novel hexacoordinate bis-bipyridylsilicon(IV) complexes have been synthesized by reacting [Si(bipy)2I2]I2 with the appropriate alcohol or diol. Characterization was done and crystal structures have been obtained for the complexes: [Si(bpy)2(OMe)2]I2, [Si(bpy)2(-OCH2CH2O-)](I)(I3), [Si(bpy)2(OPh)2](I3)2, [Si(bpy)2(cat)](PF6)2, [Si(bpy)2(bph)](PF6)2, and [Si(dmbpy)2(OH)2]I2 (bpy= 2,2'bipyridine, dmbpy = 4,4'-dimethyl-2,2'-bipyridine, bbbpy = 4,4′-di-tert-butyl-2,2′-dipyridyl cat= 1,2-benzenediolato, bph=2,2'-biphenolato ligand). Two of these new hexacoordinate silicon diol complexes has been synthesized and tested for catalytic activity. Dihydroxy-bis-(4,4′-di-tert-butyl-2,2′-dipyridyl)silicon(IV) and dihydroxy-bis-(4,4'-dimethyl-2,2'-bipyridine)silicon(IV) were synthesized and found to be quite soluble in organic solvents due to the t-butyl or methyl groups on the bipyridine. Catalytic studies, such as the addition of indole to trans-β-nitrostyrene, show that these complexes can act similar to other silicon diol catalysts.