Liquid crystalline hexa-amides and side chain polysiloxanes of azacrown [18]-N6

Abstract The hexa-4-dodecyloxybenzoyl derivative 1 of azacrown [18]-N6 was originally reported to have a ‘tubular’ mesophase on the basis of its large central ring and 6-fold symmetry. Starting in the mesophase, annealing of 1 under a cover slip results in formation of a new crystalline phase that melts directly to an isotropic liquid at the temperature previously observed for the mesophase to isotropic transition. Thus the phase behaviour of 1 is kinetically controlled. The analogous hexa-3,4-bisdodecyloxybenzoyl derivative 2 of azacrown [18]-N6 has no kinetic limitations to its phase changes and has an enantiotropic columnar liquid crystalline phase. We have synthesized side chain copolysiloxanes with a (CH2)11 spacer and 75–84 per cent by weight of the same 4-dodecyloxybenzoyl-[18]-N6 mesogen. The polysiloxanes also display a liquid crystalline phase.