Preparation and Solution Polymerization of Diacetylenes

Bruce A. Hathaway and Angela M. Scates
Department of Chemistry, Southeast Missouri State University, Cape Girardeau, MO 63701-4799
J. Chem. Educ., 1997, 74 (1), p 111
DOI: 10.1021/ed074p111
Publication Date (Web): January 1, 1997
History, Education, and Documentation

Abstract

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.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Polymer Chemistry

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Synthesis
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  • Received: August 03, 2009

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