Poly(thiaheterohelicene) derived from the long-alkylated polysulfonium precursor

Ichiro Takemura, Risa Sone, Hiroyuki Nishide

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Poly[4,6-bis(dodecylthio)-1,3-phenylene-alt-2-methyl-1,3-phenylene] (Poly-S) was synthesized via Suzuki-Miyaura coupling of 1,3-dibromo-2,6-bis(dodecylthio)benzene and 2-methyl-1,3-phenylenebis (pinacol borate). After quantitative oxidation of the pendant sulfide moiety to the sulfoxide derivative (Poly-SO), the m-linked benzene rings were fused via intramolecular ring-closing condensation with excess triflic acid to form the corresponding poly(sulfonium cation) (Poly-S+) with a helical structure. Poly-S+ was quite soluble in non-polar solvents due to the long alkyl dodecyl chain. The Poly-S+ film, especially the film cast from its acetone solution, gave a polarized optical micrograph, suggesting an oriented structure of the helical poly(sulfonium) derivative. The X-ray diffraction pattern of the film supported a hexagonal columnar packing of the polymer. The polysulfonium derivative in the film state was converted to the corresponding poly(thiaheterohelicene) (Poly-TH) via the dealkylation with a basic potassium hydroxide methanol solution or pyridine. The Poly-TH film was doped with iodine. Its conductivity was enhanced about 30 times when compared to that of the undoped film.

Original languageEnglish
Pages (from-to)1092-1096
Number of pages5
JournalPolymers for Advanced Technologies
Volume19
Issue number8
DOIs
Publication statusPublished - 2008 Aug

Fingerprint

sulfoxide
Benzene
Derivatives
Potassium hydroxide
Borates
Sulfides
Acetone
Iodine
Pyridine
Diffraction patterns
Methanol
Cations
Condensation
Polymers
Positive ions
X ray diffraction
Oxidation
Acids
pyridine
trifluoromethanesulfonic acid

Keywords

  • π-conjugated polymer
  • Electronic property
  • Helicene
  • Self-assembly

ASJC Scopus subject areas

  • Polymers and Plastics

Cite this

Poly(thiaheterohelicene) derived from the long-alkylated polysulfonium precursor. / Takemura, Ichiro; Sone, Risa; Nishide, Hiroyuki.

In: Polymers for Advanced Technologies, Vol. 19, No. 8, 08.2008, p. 1092-1096.

Research output: Contribution to journalArticle

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