Design, synthesis and properties of mesogen jacketed liquid crystalline polymers with fluorinated triphenylene pendants

Abstract

Discotic liquid crystalline polymers (DLCPs) combining the advantages of discotic liquid crystals and polymers yet have been less developed compared to the calamitic counterparts mainly due to lack of DLCP materials. Here, mesogen-jacketed liquid crystalline polymers with pendant fluorinated triphenylene were successfully synthesized via proper polymerizations of the corresponding monomers respectively. Nuclear magnetic resonance spectroscopy (both 1H NMR and 13C NMR), time-of-flight mass spectrometry (MALDI-TOF MS), Fourier transform Infrared (FT-IR) spectroscopy and other characterization methods were used to confirm the structure of the products. The mesomorphic properties of the obtained triphenylene monomers with unsaturated flexible tails and resulting polymers were investigated by polarizing optical microscopy (POM), differential scanning calorimetry (DSC), and X-ray diffractometer (XRD). The propargylene-containing monomer shows a smectic liquid crystals phase and the pentynylene monomer exhibit a highly ordered columnar helical liquid crystal phase. The three side chain polymers containing fluorinated triphenylene have good thermal stability (decomposition temperature of 350 °C or above). At the same time, the polymers prepared by the polymerization of propargylene-containing monomers have both hexagonal columnar phase (Colh) and rectangular columnar phases (Colr). The polymers with long spacer chains derived from Methyl acrylate have a hexagonal columnar structure (Colh). The fluorinated triphenylene monomers and polymers with ordered liquid crystal phases synthesized in this work provide useful inspiring for structural modifications of DLCPs and are promising for applications in organic optoelectronics.