The reaction of oligo (2-ethynylpyridines)(L1–L8) with copper (I) ions proceeded smoothly to afford tri-, tetra-, and pentanuclear triple-stranded helicates (CL1–CL8) in good yields. If a chiral ligand was used, the stereoselective self-assembly of chiral helicates with one particular chirality was achieved in the solid state. Racemization of copper (I) helicates was also observed in solution.