In order to promote interchain electronic connections in conducting polymers, three dipyrrolyl monomers have been synthesized, with conjugated spacers mimicking chains of the oligo-phenylene, oligo-phenol and oligo-aniline type. The electrochemical behaviour of these molecules as well as the characteristics of the resulting polymers have been investigated, with the help of molecular modelling (AM1-SM2). Convergent results, obtained by cyclic voltammetry, quartz crystal microbalance and ESCA, demonstrate that both pyrrolyl moieties are involved in the polymerization process, leading therefore, to ladder-like structure polymers. FTIR studies show strong interactions between the polymer backbone and the conjugated bridges.