New thermotropic symmetrical and unsymmetrical azomethine with azobenzene unit and fluorinated alkyl chain: Synthesis and characterization

Abstract A new thermotropic liquid crystals containing azobenzene unit and imine linkages were synthesized via condensation of 4-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyloxy)benzaldehyde with 4-aminoazobenzene (AzoAz-1) and 4,4′-diaminoazobenzene (AzoAz-2). The structures of compounds were characterized by means of NMR, FTIR spectroscopy and elemental analysis; the results show an agreement with the proposed structure. The mesomorphic behavior of the unsymmetrical AzoAz-1 and symmetrical AzoAz-2 azobenzeneimines was investigated via differential scanning calorimetry (DSC) and polarizing optical microscopy (POM). Based on the POM and DSC measurements AzoAz-1 exhibited smectic phases (SmX, SmA), while AzoAz-2 showed smectic (SmX1, SmX2, SmA) and nematic (N) mesophases. Optical properties of the azobenzeneimines were tested by UV–vis and photoluminescence (PL) spectroscopy in various solvents. Preliminary investigations of electrical properties of the new compounds were carried out by current–voltage (I–V) measurements performed on ITO/compound/Al device.