Biphenylene dimers, which may be considered as "macrocyclic" 2 x 2 fragments of net 1 and dimeric fragments of a double-stranded polymer, 5, are prepared. X-ray crystallography on two polymorphs of the dimer 9 reveals that its bond alternation is analogous to that in biphenylene; the tetraphenylene part of 9 has approximately C-2h symmetry with a small dihedral angle (<12 degrees) between the benzene rings in the adjacent biphenylenes. Cyclic voltammetry of 9 gives two reversible waves corresponding to a radical anion and a dianion; the lithium and potassium salts of these anions, 9(.-), M(+) (M=Li, K) and 9(2-), 2M(+) (M=Li, K), were generated and characterized by ESR, NMR, and UV-vis spectroscopies. The spectral data for the dianions are compatible with classical structures; no evidence for "in-plane aromaticity" is found. For polymer 5, a localized band and large density of states near the Fermi level are found, using extended Huckel theory calculations.