The styrene analog 3 was synthesized according to a previously reported procedure by our group (Figure ). Starting fromm racemic acetyl-PCP 1, kinetic resolution was employed to separate the enantiomers, followed by elimination to obtain the desired vinyl-PCP 3. The synthesis of N-acetyl-amino-vinyl-PCP (Figure ) and diazoacetyl-4-methylPCP (Figure ) follow similar routes. The use of two equivalents in step a, as depicted in Figure , leads to an earlier reported procedure, and the desired product was synthesized in two steps via acetoacetyl-PCP product 8. Other products, as depicted in Figure , are planned to investigate the effects and interactions of side chains and the backbone in chiral PCP-based polymers and to highlight the possibilities for easily varying the structural and complex functions of the polymers. For example, the insertion of spacers such as alkyl groups with different lengths, can vary the steric congestion drastically and therefore invoke supramolecular structures. Shorter distances could lead to the forced formation of helices or similar structures, including an additional level of chirality to the polymer. On the other hand, elongating the spacers could benefit polymerization efficiency. The supramolecular structure could be achieved from difunctionalized PCP monomers forming a polymeric network. Also, the backbone can be extended from C1 and C2 moieties to C3 and higher by adjusting the polymerization method. While this mainly affects sterics, additional heteroatoms such as oxygen can also result in altered physico-chemical properties. The insertion of functional groups is also an important possibility to extend the range of PCP polymers currently under investigation in our group.