A series of 3-fluorinated 4-alkoxystilbazoles (n-3F-OPhVPy) and some of the related 2-fluorinated derivatives (n-2F-OPhVPy) have been synthesized; unlike their non-fluorinated counterparts, these new stilbazoles are non-mesomorphic. A single crystal structure determination of 3-fluoro-4-undecyloxy-4′-stilbazole shows the molecule to be planar,transwith respect to the double bond and to crystallize in only one of two possible extreme rotational conformers. Reaction of these fluorinated stilbazoles with [IrCl(COD)]2under CO affords the complexescis-[IrCl(CO)2(n-XF-OPhVPY)] which are non-mesomorphic for X = 3, but have monotropic phases for X = 2.