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Phenyleneethynylene Macrocycle-Fused Phenylacetylene Monomers: Synthesis and Polymerization

✍ Scribed by Takashi Kaneko; Takahiro Horie; Shinji Matsumoto; Masahiro Teraguchi; Toshiki Aoki

Publisher
John Wiley and Sons
Year
2009
Tongue
English
Weight
854 KB
Volume
210
Category
Article
ISSN
1022-1352

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✦ Synopsis

Abstract

Phenyleneethynylene macrocycle‐substituted acetylenes were synthesized by repetition of the Sonogashira coupling reaction, and the elimination reaction of the terminal acetylene protecting group. The monomers were polymerized with a rhodium catalyst, [Rh(nbd)Cl]~2~, at the terminal acetylene unit, and the polymerization mixtures were purified by precipitating into methanol to yield the corresponding poly(phenylacetylene) derivatives as yellow‐red powders, which had a high degree of polymerization ($\overline {DP}$ ≈ 500) in spite of their steric bulkiness. The trimethylsilyl and pentamethyldisiloxanyl groups of polymers improved their solubility, and the polymers were soluble in common organic solvents, such as toluene, chloroform and tetrahydrofuran.

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