Synthesis and mesomorphic properties of banana-shaped achiral molecules with central and lateral halogen substituents

Three banana-shaped achiral compounds, derivatives of 4-chloro-1,3-phenylene bis[4-(4-n-decanyloxyphenyliminomethyl)benzoate], were synthesized with variation of a substituent (X = H, F, or Cl); their antiferroelectric properties are described. The mesomorphic and switching properties were characterized by polarizing optical microscopy, differential scanning calorimetry, triangular wave method, and X-ray diffraction. The introduction of a lateral halogen substituent in the Schiff's base moiety prevents the regular stacking of the molecules, resulting in a decrease of melting temperature and leads to formation of the switchable SmC* phase in the melt. All of the compounds showed antiferroelectric switching, and their values of spontaneous polarization on reversal of an applied electric field were 260, 480, and 300 nC cm(-2), respectively, for X = H, F and Cl.