Many organic (opto)electronic devices rely on organic materials to adopt polyene-like quinoidal structures under operationally-relevant scenarios, a phenomenon that can only be realized by breaking aromaticity in these systems. In this context, improving the polyene-character of a material is considered a promising approach to promoting quinoid formation that can be accomplished by introducing non-aromatic π-conjugated subunits into the macromolecular scaffold. Unfortunately, the pool of appropriate precursors is severely limited, an issue that must be addressed if materials that exhibit the desirable attributes of a polyene and polyaromatic are to be realized. This presentation will describe a convenient and efficient route to cyclopentadiene-containing π-conjugated (macro)molecules. Highlights include the results of a comparative analysis between the aryl/dienyl hybrids and their aromatic congeners that show a propensity of the diene moiety to reduce the optical band gap of a π-conjugated system without compromising its planar structural topology.