Synthesis of new liquid crystal Schiff’s bases bearing ester moiety, DFT calculation and mesomorphic studies

Abstract

A new homologues series of liquid crystalline material (E)-4-(((3,4-dimethylphenyl) imino) methyl) phenyl4-n-alkoxybenzoate (SBn) synthesized. SBn compounds was subjected to analysis using infrared spectroscopy, proton magnetic resonance, 13C NMR, UV- visible and mass spectroscopy for characterization. The investigation of liquid crystalline phases and their transition enthalpies was carried out using a polarized optical microscope and differential scanning calorimetry, respectively. All compounds within the homologous series display mesogenic properties. The SB1 -SB7 homologues exhibit an enantiotropic nematic mesophase within the temperature range of 180-106 °C, while the SB14 -SB18 homologues show a smectic A mesophase at temperatures between 78-75 °C. Additionally, the SB8 -SB10 homologues exhibit a monotropic smectic A mesophase at 61-59 °C. The phase transitions observed in series SBn are compared with those of structurally related compounds to assess the influence of central linkage and lateral tail `substitution on their mesophase behavior. With the help of DFT; EHOMO and ELUMO energy gap were computed to be negative for all derivative molecules, indicating their stability and in the following order: SB4 > SB6 > SB8 > SB12. Dielectric through determined values of complex permittivity of the synthesised liquid crystal over a broad frequency range are reported. Determined static permittivity value of liquid crystal is 2.25, at room temperature. The compound SBn exhibited a relaxation peak in the dielectric loss spectra in the microwave frequency range, which may be assigned to the rotation of the end polar group of the molecule.