Synthesis and properties of poly(9-phenanthrylacetylene) and poly(1-pyrenylacetylene)

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Abstract
Substituted polyacetylenes with very wide main-chain conjugation were synthesized by the polymerization of 9-phenanthrylacetylene (9-PhnA) and 1-pyrenylacetylene (1-PyA). The polymerizations of 9-PhnA and 1-PyA with W catalysts resulted in polymers in good yields (67-95%), whereas only low yields were attainable with Mo and Rh catalysts (6-15%). The polymers obtained with W catalysts were deeply colored (dark purple), partly soluble in toluene and chloroform, and completely soluble in o-dichlorobenzene. On the other hand, those with Mo or Rh catalysts were light brown and insoluble, which means that W-based catalysts are able to produce the polymers with wider conjugation and higher solubility than do Mo and Rh catalysts. The absorption maxima and cutoff wavelengths of the polymers produced with W catalysts reached 580 and 800nm, respectively, which is a clear indication of the extremely wide conjugation of the main chain.

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