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Two Undergraduate Experiments in Organic Polymers: The Preparation of Polyacetylene and Telechelic Polyacetylene via Ring-Opening Metathesis Polymerization

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Eric J. Moorhead and Anna G. Wenzel

Joint Science Department, Claremont McKenna, Pitzer, and Scripps Colleges, Claremont, CA 91711

J. Chem. Educ., 2009, 86 (8), p 973

DOI: 10.1021/ed086p973

Publication Date (Web): August 1, 2009

Section:

History, Education, and Documentation

Abstract

The ruthenium-catalyzed ring-opening metathesis polymerization of 1,3,5,7-cyclooctatetraene (COT) to produce polyacetylene and a telechelic polymer of polyacetylene is described in a series of two experiments for the undergraduate laboratory. In the first experiment, students plate-polymerize COT and dope the resulting polyacetylene with iodine to perform resistivity studies. In the second experiment, students mix COT with TBS-protected cis-2-butene diol as a chain transfer agent to produce a telechelic polyene, which is then studied via ¹H NMR, IR, and UV–vis spectroscopy. Experimental details and the results of a test study of these experiments in an undergraduate laboratory class are discussed.

Keywords (Audience):

Upper-Division Undergraduate

Keywords (Domain):

Inorganic Chemistry

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Alkenes

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