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

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

doi:10.1002/pola.21596

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

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

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

7 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 language	English
Pages (from-to)	5403-5412
Number of pages	10
Journal	Journal of Polymer Science, Part A: Polymer Chemistry
Volume	44
Issue number	18
DOIs	https://doi.org/10.1002/pola.21596
Publication status	Published - 2006 Sept 15
Externally published	Yes

Keywords

Conducting polymers
Conjugated polymers
Macrocycles
Orientation

ASJC Scopus subject areas

Polymers and Plastics
Organic Chemistry
Materials Chemistry

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title = "Synthesis and characterization of a π-conjugated hybrid of oligothiophene and porphyrin",

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.",

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author = "Kenichi Oyaizu and Manabu Hoshino and Masuhide Ishikawa and Takuya Imai and Makoto Yuasa",

year = "2006",

month = sep,

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T1 - Synthesis and characterization of a π-conjugated hybrid of oligothiophene and porphyrin

AU - Oyaizu, Kenichi

AU - Hoshino, Manabu

AU - Ishikawa, Masuhide

AU - Imai, Takuya

AU - Yuasa, Makoto

PY - 2006/9/15

Y1 - 2006/9/15

N2 - 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.

AB - 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.

KW - Conducting polymers

KW - Conjugated polymers

KW - Macrocycles

KW - Orientation

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JO - Journal of Polymer Science, Part A: Polymer Chemistry

JF - Journal of Polymer Science, Part A: Polymer Chemistry

IS - 18

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

Abstract

Keywords

ASJC Scopus subject areas

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