Isophthalic acid based mesogenic dimers: Synthesis and structural effects on mesophase properties

Two series of mesogens based on isophthalic acid and side arms containing two and three phenyl rings linked through azomethine or ester groups were synthesized via divergent approach. Another type of structurally similar mesogen was synthesized via convergent approach in which the azomethine groups were replaced by ester groups. All the synthesized mesogens and their intermediates were structurally well characterized using FT-IR, 1H NMR, 13C NMR and EI-MASS spectrometry. The mesophase characterization was carried out using hot stage-polarizing optical microscopy (POM), differential scanning calorimetry (DSC) and X-ray diffraction (XRD) techniques. The structural changes made in the mesogens i.e. increase of terminal chain length and replacement of azomethine groups with ester groups decreased the transition temperatures whereas the increase of side arm length improves the phase stability to a wide temperature range. Nematic phase was observed for the mesogens with short terminal chain length whereas the smectic polymorphism was observed on increasing the terminal chain length. The structural modification (three ring) on the side arm core stabilizes the mesophases enantiotropically.

► Mesogenic dimers containing two and three phenyl ring side arm core were synthesized. ► The structural changes made in the mesogens causes significant effect in the melting and clearing temperatures. ► The increase of arm length stabilizes the enantiotropic fashion. ► Smectic polymorphism was observed on cooling.