The synthesis of a block copoly(3-alkylthiophene) consisting of two different P3AT blocks equipped with an H-donor and -acceptor functionality is presented. The P3ATs were synthesized using a functionalized Ni-initiator. By a series of postpolymerization reactions, including click chemistry, an H-donor and -acceptor entity was attached to the end of the polymer chains. Evidence for a quantitative functionalization of the polymers was provided by H-1 NMR and MALDI-ToF analyses. Chiral side chains were implemented on one of both blocks, allowing the study of the influence of the H-bond formation on the chiral self-assembly using UVvis and circular dichroism spectroscopy.