Pd-catalyzed Suzuki coupling is used to prepare poly(p-phenylene)s (PPPs) bearing oligo(ethylene oxide)s (OEOs) and trialkylamino groups as lateral substituents. The OEO substituents require very specific reaction conditions during monomer synthesis - presumably due to their coordinating oxygen atoms - but do not affect the subsequent Pd-catalyzed polycondensation process. In contrast to this, the lateral amino groups lower the degree of polycondensation of the PPPs considerably when their nitrogen atom is placed in the β-position of the side chains. When there is a longer spacer group between the amino nitrogen and the aromatic ring to be coupled, however, high-molecular-weight PPPs can be obtained. Provided an appropriate substitution pattern and long OEO side chains are used, the resulting PPPs are readily soluble not only in organic solvents but even in aqueous media. For one of these PPPs, the degree of protonation has been determined as a function of pH, using 1H and 13C NMR spectroscopy as well as potentiometry. It is shown that the polymer is completely deprotonated at pH > 10.5 and quantitatively protonated at pH < 4.0.