A series of alkoxy-substituted hydroxybutyl dibenzoates and four halogen-substituted compounds were synthesised in quantitative yields. The structures of the molecules were confirmed by Fourier transform infra-red, 1 H nuclear magnetic resonance (NMR) and 13 C-NMR spectroscopy and gas chromatography-mass spectrometry. The stabilities of the synthesised compounds were determined by thermogravimetric analysis. The mesomorphic behaviour was investigated using differential scanning calorimetry, polarising optical microscopy and wide-angle X-ray diffraction (WAXD) analysis. It was observed that the compounds with alkoxy tails form the typical fan-like texture of a smectic liquid crystalline phase between the melting point and clearing temperature. WAXD experiments confirmed the formation of smectic liquid crystalline phases. The halogen-substituted compounds were incapable of forming the liquid crystalline phase on heating.
The title compound, C17H16O5, is an important intermediate for the synthesis of side-chain ligands for polymeric liquid crystals. The propoxy and benzoic acid groups subtend dihedral angles of 4.36 (6) and 55.35 (6)°, respectively, with the central benzoyloxy unit. The crystal structure is stabilized by an intermolecular O—H⋯O hydrogen bond.
The title compound, C15H11FO2, is an important intermediate in the synthesis of side-chain ligands for polymeric liquid crystals. The vinyl group is almost coplanar with both the aromatic rings. The crystal structure is stabilized by intermolecular O—H⋯O hydrogen bonding.
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