Thermotropic liquid–crystalline properties of 4,4′-dialkoxy-3,3′-diaminobiphenyl compounds and their precursors

A series of 4,4ʹ-dialkoxy-3,3ʹ-diaminobiphenyl compounds were synthesised by three-step procedure that involves alkylation, nitration and reduction reactions. Their chemical structures were characterised by FTIR, 1H and 13C spectroscopy and elemental analysis. Their thermotropic liquid–crystalline (LC) properties were examined by a number of experimental techniques including differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), polarising optical microscopy (POM) and variable temperature X-ray diffraction (VT-XRD). The 4,4ʹ-dialkoxy-3,3ʹ-dinitrobipheyl compounds, precursors to the diamine compounds, were also examined for their thermotropic LC properties. POM studies of focal conic textures and VT-XRD of the 3,3ʹ-diaminobiphenyl derivatives having flexible alkyl chains (C6–C12) exhibited the smectic A (SmA) phase independent of the length of alkyl chains. Similarly, the 3,3ʹ-dinitrobiphenyl derivatives containing alkyl chains C7, and C9–C11 exhibit the SmA phase, those containing C8 formed the smectic C (SmC) phase and C12 formed both the SmA and smectic B (SmB) phases, respectively. The 3,3ʹ-diaminobiphenyl derivatives had excellent thermal stability in the temperature range of 237–329°C, while those of 3,3ʹ-dinitrobiphenyl derivatives were in the temperature range of 270–321°C. The 3,3ʹ-diaminobiphenyl derivatives emitted UV light both in chloroform and acetonitrile.