Synthesis and mesomorphism of diacetylene-bridged triphenylene discotic liquid crystal dimers

Abstract

Connecting two discotic mesogens via a spacer not only stabilizes the columnar mesophase but also leads to the formation of glass columnar phase, and therefore improves the physical properties of discotic liquid crystals as organic semiconductor. Here, we report the synthesis of eight diacetylene-bridged triphenylene discotic liquid crystal dimers, [C18H6(OC n H2n+1)4(OMe)O2C−C8H16−C≡C−]2, 3(n), (n = 4–8), [C18H6(OC6H13)5O2C−C8H16−C≡C−]2, 6 and [C18H6(OC6H13)5O−(CH2)m−C≡C−]2, 8(m), (m = 1, 3) by Eglinton coupling reaction. The thermotropic liquid crystal properties were studied by differential scanning calorimetry and polarized optical microscopy. The results are showed as follows: the length of peripheral alkyl chains of triphenylene influenced properties of liquid crystal dimers; dimers 3(n) (n = 5–8) and 6 had glass columnar phase, and no crystallization was observed above −50°C for all the triphenylene dimers; compared with 3(6), 6 showed higher molecular symmetry, more stable columnar mesophase and wider mesophase range. The connecting group, length and rigidity of spacer had important influence on the mesomorphism of diacetylene-bridged triphenylene discotic liquid crystal dimers.