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Synfacts 2019; 15(03): 0243
DOI: 10.1055/s-0037-1612221
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Heat On, Heat Off: A Synthesis of Polyacetylene Revisited

Contributor(s):
Timothy M. Swager
,
Benjamin R. McDonald
Edwards JH, Feast WJ. * Durham University, UK
A New Synthesis of Poly(acetylene).

Polymer 1980;
21: 595-596
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Further Information

Publication History

Publication Date:
15 February 2019 (online)

 
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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.


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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.


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