Glyoxylic functionalization of chrysene by Friedel–Crafts acylation with ethyl chloroglyoxylate or by bromination followed by substituent exchange enables the formation of bis[5]helicene-tetracarboxylates and tetracarboxdiimides through Perkin reactions and palladium-catalyzed cyclizations. Tetrasubstituted bishelicenic dichrysenoanthracenes and dinaphthochrysenes are thus obtained from chrysene in four to six steps. In the cyclization to dinaphthochrysenes, a rearrangement of the conjugated carbon skeleton is identified as side reaction. In solution, the diimides form mixtures of M,P- and M,M/P,P-diastereomers, which equilibrate at room temperature when the helices are distant but equilibrate only upon heating when the helices are close and acting in concert. The nonplanar arene geometry allows close π-contacts in two dimensions between neighboring molecules in the crystal.