The combination of redox-active ferrocene moieties, conjugated B=N units, and p-phenylene building blocks in linearly concatenated architectural arrangements has been explored. Oligo- and poly(ferrocenylene iminoborane)s have been successfully prepared, whereby in the latter case, the formation of linear polymers vs. discrete molecular macrocycles could be largely influenced by the polymerization conditions applied. In addition, a series of well-defined co-oligomers composed of ferrocenylene and p-phenylene moieties bridged by one or two B=N units in all possible combinations have been prepared, many of which have been structurally characterized using single-crystal X-ray diffraction. Pendent triisopropylphenyl groups on boron provide pronounced kinetic stabilization. Polycondensation of complementary monomers gave copolymers comprising alternating ferrocenylene and p-phenylene iminoborane building blocks, which were found to be cyclic in nature. UV-vis absorption spectroscopic and electrochemical studies provided highly valuable insights into the interaction of the different moieties over the B=N bonds, particularly, the electronic communication between the electroactive ferrocene units.