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The quasi‐epitaxial growth of vacuum‐deposited films of diacetylenes on various substrates, including uniaxially aligned polymer surfaces formed with rubbing treatment or Langmuir–Blodgett technique, is reported. The oriented polydiacetylene (PDA) films are readily obtained from these monomer films using photopolymerization. Highly oriented PDA films with excellent optical qualities have been obtained on rubbed polyethylene terephthalate surfaces. The typical dichroic ratio of these oriented PDA films is more than 100:1. This ratio is high enough to permit the application of these films to optical waveguide devices. The method for obtaining these highly oriented PDA films is described in detail. In addition, the structure, the morphology, and the optical anisotropy of these PDA films is examined by x‐ray and electron diffraction, electron microscopy, and other optical means.