The distinctive chiral features of molecular systems and their formation mechanisms are of substantial importance from the perspective of emulating nature's approach to supramolecular self-assembly as well as their diverse applications in pharmaceutical, medicinal, and other emerging materials. Chiral moieties can be incorporated into polymers either as backbone or as a side-group attached to the backbone, ultimately aiming for unique properties induced by the chirality. Besides the classical central chirality, other concepts based on helical, planar or supramolecular chirality have been investigated for their applications in life sciences and materials. Different concepts of chirality can be combined into one polymeric structure using suitable chiral monomers. The most commonly used chiral polymers recur to molecules from the chiral pool, which are limited to naturally occuring scaffolds or require multi-step synthetic approaches. Alternatively, chiral polymers need to form and maintain supramolecular structures like helices to prevent the loss of chirality through the formation of meso components. The structuring of synthetic materials by a bottom-up dimensional organizing principle, is of utmost relevance sice both structural and complex functional diversity of materials can arise from the inherent physico-chemical properties of the molecular units. For instance, polymer modulation with precise control over the structure, properties, and functions is, among various contributing factors, achieved by the design of the monomers. Assembling customized monomers offers the opportunity to create molecular systems whose structural features and functions can be precisely controlled. To achieve the goal of an easy setup for structuring chiral polymers, in this work, we have envisioned the molecular design and development of novel polymers with a chirality transcription by incorporating chiral [2.2]paracyclophane derivatives into the polymer by employing anionic and radical polymerization with the possibility of postpolymerization modification.