Liquid-crystalline heterodimesogens and ABA-heterotrimesogens comprising a bent 3,5-diphenyl-1,2,4-oxadiazole central unit

Beilstein J Org Chem. 2012:8:472-85. doi: 10.3762/bjoc.8.54. Epub 2012 Mar 30.

Abstract

Three new types of terminally connected ABA-heterotrimesogens and heterodimesogens, composed of a bent 3,5-diphenyl-1,2,4-oxadiazole central unit and one or two rod-shaped 4-cyanobiphenyl cores or one 2-phenyl-1,3,4-thiadiazole core, connected by flexible spacers, have been synthesized, and their mesomorphic behavior was studied by optical polarizing microscopy (PM), differential scanning calorimetry (DSC) and X-ray diffraction (XRD). All dimesogens exhibit broad ranges of cybotactic nematic phases (N(cybA) and N(cybC)), in some cases accompanied by additional mesophases (CybA or SmC) at lower temperature. The combination of the 3,5-diphenyl-1,2,4-oxadiazole unit with one cyanobiphenyl core leads to the removal of tilted smectic and cybotactic nematic phases (SmC, N(cybC)), which are replaced by the nontilted CybA phases and nematic phases composed of SmA-type clusters (N(cybA)). The orthogonal cybotactic nematic phases of bent-core mesogens are of special interest for achieving biaxial nematic phases of the orthorhombic type. The orthogonal (N(cybA)) and skewed (N(cybC)) cybotactic nematic phases were distinguished by XRD and optical observations.

Keywords: 1,2,4-oxadiazoles; bent-core mesogens; cybotactic nematic phases; dimesogen; liquid crystals; trimesogen.