Edwards JH,
Feast WJ.
* Durham University, UK
A New Synthesis of Poly(acetylene).
Polymer 1980;
21: 595-596
Key words
polyacetylene - conducting polymers - ROMP polymerization - retrocyclization
Significance
Polyacetylene (6) is the simplest organic conducting polymer and was pivotal to the development of
the field organic electronics, an impact that was recognized with a Nobel prize in
2000. Sensitivity to atmospheric conditions stymied early efforts towards the investigation
and application of this material. Edwards and Feast provided a method for the casting
and controlled formation of trans-polyacetylene using a creative ROMP and thermal cycloreversion of polymer 5.
Comment
Monomer 4 was prepared by the cycloisomerization of cyclooctatetraene (1) and subsequent Diels–Alder reaction with perfluorobutyne (3). Ring-opening metathesis of 4 with a titanium tetrachloride/trimethylaluminum catalyst, stereoselectively provides
polymer 5. At room temperature, this polymer decomposed to provide trans-polyacetylene (6) and 1,2-bistrifluoromethyl benzene (7) over several days. Heating under vacuum accelerates this process, providing 6in three hours.
