Polar nematic trans-4-substituted-cyclohexyl (E)-alk-2-enoates The influence of dipoles and double bonds on the transition temperatures and other physical properties

Abstract

As part of a systematic study of the factors affecting nematic phase formation, the influence of introducing dipoles (in the form of oxygen, carbonyl and carboxy groups) and steric restrictions (in the form of carbon-carbon double bonds) in various positions, configurations and combinations in a model system (4-[trans-4-pentylcyclohexyl]benzonitrile) has been investigated. On the basis of these results, we have introduced an ester group and a carbon-carbon double bond with a trans-configuration (E) into the terminal alkyl chain attached to the cyclohexyl ring of a variety of two- and three-ring nematic mesogens of positive dielectric anisotropy. This is a new combination of a polar ester group (dipole effect) and the added rigidity imposed by the double bond (steric effect). Most of the new (E) alk 2-enoates containing two rings in the molecular core possess high melting points. Only a few two ring esters exhibit nematic phase, although the clearing point of those esters exhibiting mesomorphic behaviour was high. The corresponding three-ring (E)-alk-2-enoates incorporating an additional phenyl or cyclohexane ring also possess high melting and clearing points, as well as wide nematic ranges. No smectic mesophases could be observed for any of the (E)-alk-2-enoates synthesized. Comparisons with the corresponnding derivatives incorporating either just an ester group, or just a carbon-carbon double bond in the same position indicate that synergetic effects lead to higher clearing points than would otherwise have been expected. The new (E)-alk-2-enoates possess a surprisingly moderate viscosity for esters. The high value of the elastic constant ratio k ₃₃/k ₁₁ is of advantage for mixtures designed for supertwisted nematic LCDs.