The influence of vicinal threo-difluorination on electro-optic and mesogenic properties of propyleneoxy-linked nematic liquid crystals

A protocol for the preparation of a series of liquid crystals is presented, where the structures carry a central propyleneoxy motif carrying two vicinal threo-C-F bonds. The negative dielectric anisotropy (-Delta epsilon) of the resultant liquid crystals has been explored. The stereoelectronic relationship between the vicinal C-F bonds was anticipated to orientate the fluorine atoms gauche to each other when the propylene chain is extended. This is shown to be the case. This orientation of the C-F bonds generates a net dipole perpendicular to the molecular axis, a prerequisite for the design of dielectrically negative liquid crystals. However the molecules adopt a conformation where one C-F bond reinforces the net molecular dipole, and the other has a counter effect, thus the introduction of the motif has an almost neutral effect on dielectric anisotropy (Delta epsilon(virt)) of these candidate liquid crystals. However, introduction of the difluoro motif raises the melting points of the liquid crystals and increases their conformational rigidity. (C) 2014 Elsevier Ltd. All rights reserved.