Resumen de Preparation and Solution Polymerization of Diacetylenes

Bruce A. Hathaway, Angela M. Scates

• Polymeric Diacetylenes ("Polydiacetylenes", or PDA's) are being investigated for their Non-Linear Optical (NLO) properties. PDA's have also been advocated by Patel and Yang (J. Chem. Educ. 1983, 60, 181-5) as a system for teaching polymer science, although these authors did not publish a synthesis of the diacetylene precursor to their PDA in this article. Most published student laboratory syntheses of symmetrical diacetylenes follow Hay's procedure (J. Org. Chem. 1962, 27, 3320-1), with some modifications for using air as a source of oxygen. We report a simpler procedure, which has been useful in preparing a variety of diacetylenes. Yields range from 35-70%, and may be improved by increasing the reaction time. In addition, we have developed conditions suitable for solution polymerization of these diacetylenes to PDA's, using short-wave UV light. These conditions complement the solid phase polymerization conditions described by Patel and Yang.