The synthesis of laterally fluorinated alkoxystilbazoles and some of their mesogenic complexes with Ir(I). The molecular structure of trans-4-undecyloxy-3-fluoro-4′-stilbazole

Abstract

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, trans with 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)]₂ under CO affords the complexes cis-[IrCl(CO)₂(n-XF-OPhVPY)] which are non-mesomorphic for X = 3, but have monotropic phases for X = 2.