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Synfacts 2008(4): 0364-0364  
DOI: 10.1055/s-2008-1042840
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Transition-Metal-Free Synthesis of Poly(phenylene Ethynylene)s

Contributor(s): Timothy M. Swager, Kristin L. Glab
T. Dutta, K. B. Woody, M. D. Watson*
University of Kentucky, Lexington, USA
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Publication History

Publication Date:
19 March 2008 (online)

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Significance

The properties of poly(arylene ethynyl­ene)s (PAE) can be optimized for (opto)electronic applications by structural refinement. Typical syntheses involve palladium-catalyzed cross-couplings or acyclic diyne metathesis. In this communication, poly(phenylene ethynylene)s with alternating aryl and perfluoroaryl units were synthesized in high molecular weight (9-153 kDa, depending on conditions used) and high yield (75-98%) via nucleophilic aromatic substitution of perfluorobenzene with silyl acetylenes 1 using catalytic fluoride ion. Poly 1 is easily purified since the only side product is a gas (TMSF) and the catalyst is removed with aqueous treatment.