A Novel Synthesis of Polymers with Dimensionally Extended pi-Conjugation by Solid-State Polymerization and Their Physical Properties

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Some tetrayne and hexayne derivates were synthesized and then polymerized in the solid-state by gamma-ray. The resulting pi-conjugated polymers looked like metal. The tetrayne compounds with urethane groups were the most polymerizable. The similar compounds having aryl groups gave large enough crystals for X-ray single crystal structure determination, resulting in the confirmation of the polymer structure, i.e. a polydiacetylene with directly bound diacetylenic moiety. However, it has become apparent that the reaction of diacethlenic moiety to ladder polymer does not proceed so easily. UV absorption peaks due to exciton were shifted bathochromically with extending pi-conjugation, and the degree of the shift was proportional to the number of acetylene group in the side chain. The value of chi^<(3)> was ca.10^<-9> esu, which was increased about one order of magnitude greater than ordinary polydiacetykenes.