Triphenylene discotic liquid crystal trimers synthesized by Co(2)(CO)(8)-catalyzed terminal alkyne [2 + 2 + 2] cycloaddition

The synthesis of star-shaped discotic liquid crystal trimers using Co(2)(CO)(8)-catalyzed terminal alkyne [2 + 2 + 2] cycloaddition reaction is reported. The trimers consist of three triphenylene discotic units linked to a central 1,2,4-trisubstituted benzene ring via flexible spacers. The trimers were synthesized in the yields up to 70% by mixing the monomers with 10 mol % of Co(2)(CO)(8) as the catalyst in refluxing 1,4-dioxane. The liquid crystalline properties were investigated by using polarizing optical microscopy (POM), differential scanning calorimetry (DSC) and X-ray diffraction (XRD). Trimer 4 with an ester connecting group and a longer spacer exhibited a rectangular columnar mesophase, while 5b and 5c possessing an ether linkage and a shorter spacer display a hexagonal columnar mesophase. The connecting functional group and the length of the flexible spacer between the central benzene ring and the triphenylene units have pivotal influence on the mesomorphism.