Synthesis and functionalization of diketopyrrolo[3,4‐ c ]pyrrole (DPP) derivatives containing chiral groups able to induce a strong chiral perturbation of the DPP core are still a challenging task. We report in this work the straightforward preparation of four bis([4]helicene)‐DPP and bis([4]thiahelicene)‐DPP dyes upon the condensation of 2‐CN‐[4](thia)helicene precursors, followed by their N‐alkylation by nucleophilic substitution (compounds 9 – 11 ) or by a Mitsunobu‐type strategy (compound 12 ). Compound 12 , which contains sec ‐phenylethyl groups attached to the nitrogen atoms, has been obtained as ( R , R ) and ( S , S ) enantiomers. The four DPP‐helicenes are luminescent in solution, while the N‐benzyl ( 10 ) and N ‐ sec ‐phenethyl ( 12 ) are emissive in the solid state as well. The chiroptical properties of compound 12 in solution and in the solid state indicate a strong chiral perturbation provided by the α‐stereogenic centres, in spite of the stereodynamic nature of the [4]helicene flanking units.