A new synthetic approach based on (−)-menthone for chiral liquid crystals

Abstract

Starting from (−)-menthone, a new chiral building block useful for liquid crystal preparation was synthesized. This chiral moiety was attached to selected phenols under mild conditions by esterification. Rigid cores of tolanebenzoates and phenylbenzoates were prepared using the palladium cross-coupling reaction or by traditional liquid crystal synthesis methods. This convergent approach ended with a second esterification or palladium cross-coupling reaction to furnish new liquid crystal materials with smectic A, smectic C* and N* phases, as well as blue phases (BP). Thermal behavior, and the effect of chiral moiety branches and molecular packing in the smectic phases, have been investigated using differential scanning calorimetry, optical microscopy and X-ray diffraction.

Notes

^†Compounds 4-ethynylbenzoic acid and 4-ethynylphenol decompose with light or on heating and were synthesized from 4-bromoethyl benzoate and 4-bromophenyl acetate, respectively, using the procedure described in [15].