Conjugated graft copolymers consisting of a chiral poly(phenyleneethynylene) (PPE) backbone and poly(3-hexylthiophene) side chains (P3HT) with different grafting degrees were synthesized. While PPE was prepared by classical Sonogashira couplings, the end-functionalized P3HT was prepared by a controlled Kumada catalyst transfer poly-condensation (KCTP) allowing the installation of an acetylene end group. After some postpolymerization reactions on the PPE to introduce azide groups, the P3HT was clicked to the PPE through the CuAAC coupling reaction. Subsequently, the (chiral) self-assembly of these materials was studied by means of UV vis and CD spectroscopy, AFM, and DSC. Finally, fluorescence spectroscopy is used to study the quenching of the PPE fluorescence by P3HT.