The synthesis of the first two arylenealkyne conjugated macrocycles containing a long alkylene bridge via Glaser coupling of template-directed tetraacetylenes was reported. Tetraacetylene intermediates with complex structures were constructed rapidly via quadruple Hagihara coupling of monoprotected bisacetylenes to appropriate tetraiodides and subsequent desilylation. The characterization of such compounds was carried out by NMR, GPC and UV-Vis spectra. Unfortunately, the two compounds were not liquid crystals and had no biaxial nematic mesophase character as expected.
