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AbstractMono‐ and di‐boranil‐substituted helicenes were prepared by BF2‐borylation of the corresponding anils, readily synthesized by condensation of 2‐amino‐ and 2,15‐diamino‐helicenes with 4‐(diethylamino)salicylaldehyde. After enantiomeric resolution using HPLC, their chiroptical properties including circularly polarized fluorescence in solution and in PMMA films were investigated and rationalized with the help of NMR, X‐ray and quantum‐chemical calculations.