Abstract Our synthetic efforts toward the realization of cross-conjugated macrocycles containing 2, 6-diethynylpyridine sub-units are described. Macrocycle 4b was efficiently constructed from easily accessible building blocks using a series of palladium-catalyzed cross-coupling and copper-catalyzed homocoupling reactions. The synthesis, characterization and solid state characteristics of this macrocycle, as well as its precursors ...