The synthesis of new heterocyclic oligo (phenylene) analogues based on soluble, nonaggregating 1, 2-diazines is reported. Improved palladium-catalyzed reductive coupling methods were developed to allow for the preparation of large quantities of iptycene-derived bipyridazines and biphthalazines, and the controlled synthesis of well-defined oligomers up to sexipyridazine. Crystallographic, spectroscopic, and computational evidence indicate ...