Poly(thiaheterohelicene): Control of fused helical structure and its morphology

Ichiro Takemura, Yuko Masumoto, Hiroyuki Nishide

Research output: Chapter in Book/Report/Conference proceedingConference contribution

Abstract

Helicenes are characterized by fused ring π-conjugation and its stiff structure, and have been expected to be stable magneto-optical molecules. However, they must be synthesized stepwise, therefore, there were no reports on synthesis of the helicenes having sufficient length as a π-conjugated polymer. We have developed the facile synthesis of the poly(thiaheterohelicene)s using ring-closing reaction via the sulfonium salts. Poly(1,3-phenylene)s bearing thioalkyl groups were polymerized with Pd(0) catalyst. Ring-closing reaction with strong acid followed oxidation reaction of the sulfide to produce the sulfonium derivatives. Poly(thiaheterohelicene)s were synthesized via dealkylation reaction of the sulfonium polymers with strong base. Its helicity was controlled with hydrophobic effect or inter-molecular interaction. Polarized optical micrographic imaging of poly sulfonium bearing dodecylthio groups revealed birefringence and it was changed with casting solvents. Radical formation on I2-doped poly(thiaheterohelicene) was detected with UV-vis and ESR spectrum. The electrical conductivity of the doped poly(helicene) was developed than the undoped polymer.

Original languageEnglish
Title of host publicationPolymer Preprints, Japan
Pages3034-3035
Number of pages2
Volume55
Edition2
Publication statusPublished - 2006
Event55th Society of Polymer Science Japan Symposium on Macromolecules - Toyama
Duration: 2006 Sep 202006 Sep 22

Other

Other55th Society of Polymer Science Japan Symposium on Macromolecules
CityToyama
Period06/9/2006/9/22

Keywords

  • Conjugated polymer
  • Helicene
  • Ring closing
  • Sulfonium salt

ASJC Scopus subject areas

  • Engineering(all)

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    Takemura, I., Masumoto, Y., & Nishide, H. (2006). Poly(thiaheterohelicene): Control of fused helical structure and its morphology. In Polymer Preprints, Japan (2 ed., Vol. 55, pp. 3034-3035)