Organic pi-conjugated polymers have emerged as one of the most fascinating classes of materials as they have found utility in a host of plastic electronics technologies. The distance between pi-systems and their relative orientation dictate energy/charge transfer, conductivity, and photophysical properties of these materials in bulk. This Feature Article discusses pi-conjugated polymers and model compounds in which specific inter-pi-system interactions are covalently enforced and the effect that the scaffolding, has on optoelectronic properties.