Synthesis and characterization of a π-conjugated hybrid of oligothiophene and porphyrin

Kenichi Oyaizu, Manabu Hoshino, Masuhide Ishikawa, Takuya Imai, Makoto Yuasa

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

5-(3-Thienyl)-10,15,20-triethyl-21H,23H-porphine (H2(ttep)) was synthesized and characterized. Oxidative polymerization of H2(ttep) gave a novel oligomeric porphyrin linked at the 2,5-positions of the thienyl group. Electric conductivity of 4 × 10-1 S/cm after I 2 doping indicated that the oligomer had a π-conjugated structure with a delocalization of π electrons over the thienylene backbone. PM3 calculations revealed a low HOCO-LUCO gap, which was consistent with the relatively high electric conductivity. Regioregular (head-to-tail) structure was inferred from spectroscopic and calculational results. The pendant porphyrin groups formed a regular J-type array along the thienylene backbone, which was indicated by a significant red shift of the Soret band maximum.

Original languageEnglish
Pages (from-to)5403-5412
Number of pages10
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Volume44
Issue number18
DOIs
Publication statusPublished - 2006 Sep 15
Externally publishedYes

Fingerprint

Porphyrins
Electric conductivity
Oligomers
Polymerization
Doping (additives)
Electrons
porphine

Keywords

  • Conducting polymers
  • Conjugated polymers
  • Macrocycles
  • Orientation

ASJC Scopus subject areas

  • Polymers and Plastics
  • Materials Chemistry

Cite this

Synthesis and characterization of a π-conjugated hybrid of oligothiophene and porphyrin. / Oyaizu, Kenichi; Hoshino, Manabu; Ishikawa, Masuhide; Imai, Takuya; Yuasa, Makoto.

In: Journal of Polymer Science, Part A: Polymer Chemistry, Vol. 44, No. 18, 15.09.2006, p. 5403-5412.

Research output: Contribution to journalArticle

Oyaizu, Kenichi ; Hoshino, Manabu ; Ishikawa, Masuhide ; Imai, Takuya ; Yuasa, Makoto. / Synthesis and characterization of a π-conjugated hybrid of oligothiophene and porphyrin. In: Journal of Polymer Science, Part A: Polymer Chemistry. 2006 ; Vol. 44, No. 18. pp. 5403-5412.
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