[2.2]Paracyclophane (cyclophanyl; PCP) is is a prevalent 3D scaffold of intriguing structural and electronic properties which exhibits planar chirality upon substitution and is therfore widely investigated in asymmetric synthesis as planar chiral ligands, catalysts, chiroptical, and optoelectronic materials. PCP-derived materials dealing with planar chirality and through-space conjugation have been the subject of comprehensive research. PCP and derivatives have previously been used in polymer chemistry for the preparation of π-stacked conjugated polymers by employing electrochemical, transition metal-catalyzed coupling reactions or various polycondensation approaches. Monomers based on [2.2]paracyclophanes offer intrinsically planar chirality and can be widely functionalized. Grafting synthetically tunable functional moieties can also enable post-polymerization modification for optimizing and tuning structural and functional properties of the polymer. By using carefully chosen reaction parameters and transformation steps, different polymerizable groups can be selectively positioned at either one or both benzene rings of the PCP core to enable polymerization.