2,6,10-Tris(bithiophenyl)triphenylene: Synthesis and high-spin alignment in its p-doped radical derivative

Takeshi Ibe; Hiroaki Umeda; Hiroyuki Nishide

doi:10.1016/j.synthmet.2009.01.003

2,6,10-Tris(bithiophenyl)triphenylene: Synthesis and high-spin alignment in its p-doped radical derivative

Takeshi Ibe, Hiroaki Umeda, Hiroyuki Nishide^*

^*Corresponding author for this work

Waseda Research Institute for Science and Engineering

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

4 Citations (Scopus)

Abstract

2,6,10-Tris[5′-(5-hexyloxyphenyl-2,2′-bithiophenyl)]-3,7,11-tris(hexyloxy)tripheneylene (2) was designed and synthesized as a π-conjugated platform to produce its tris(cationic radical) derivative (1) in a non-Kekulé and nondisjoint fashion. An electrochemical study revealed the chemically reversible redox property of 2. Gaseous antimony pentachloride-doping of 2 dispersed in a polystyrene matrix gave its cationic radical. It was chemically stable with a half-life >2 weeks and displayed a triplet ground state based on an ESR measurement. A high-spin state with S = 3/2 for 1 was proved by the magnetization and magnetic susceptibility.

Original language	English
Pages (from-to)	788-791
Number of pages	4
Journal	Synthetic Metals
Volume	159
Issue number	9-10
DOIs	https://doi.org/10.1016/j.synthmet.2009.01.003
Publication status	Published - 2009 May

Keywords

π-Conjugated molecule
Arylthiophene
Ferromagnetic interaction
Non-Kekulé molecule
Triphenylene

ASJC Scopus subject areas

Mechanical Engineering
Mechanics of Materials
Materials Chemistry
Metals and Alloys
Electronic, Optical and Magnetic Materials
Condensed Matter Physics

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10.1016/j.synthmet.2009.01.003

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title = "2,6,10-Tris(bithiophenyl)triphenylene: Synthesis and high-spin alignment in its p-doped radical derivative",

abstract = "2,6,10-Tris[5′-(5-hexyloxyphenyl-2,2′-bithiophenyl)]-3,7,11-tris(hexyloxy)tripheneylene (2) was designed and synthesized as a π-conjugated platform to produce its tris(cationic radical) derivative (1) in a non-Kekul{\'e} and nondisjoint fashion. An electrochemical study revealed the chemically reversible redox property of 2. Gaseous antimony pentachloride-doping of 2 dispersed in a polystyrene matrix gave its cationic radical. It was chemically stable with a half-life >2 weeks and displayed a triplet ground state based on an ESR measurement. A high-spin state with S = 3/2 for 1 was proved by the magnetization and magnetic susceptibility.",

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T2 - Synthesis and high-spin alignment in its p-doped radical derivative

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AU - Umeda, Hiroaki

AU - Nishide, Hiroyuki

PY - 2009/5

Y1 - 2009/5

N2 - 2,6,10-Tris[5′-(5-hexyloxyphenyl-2,2′-bithiophenyl)]-3,7,11-tris(hexyloxy)tripheneylene (2) was designed and synthesized as a π-conjugated platform to produce its tris(cationic radical) derivative (1) in a non-Kekulé and nondisjoint fashion. An electrochemical study revealed the chemically reversible redox property of 2. Gaseous antimony pentachloride-doping of 2 dispersed in a polystyrene matrix gave its cationic radical. It was chemically stable with a half-life >2 weeks and displayed a triplet ground state based on an ESR measurement. A high-spin state with S = 3/2 for 1 was proved by the magnetization and magnetic susceptibility.

AB - 2,6,10-Tris[5′-(5-hexyloxyphenyl-2,2′-bithiophenyl)]-3,7,11-tris(hexyloxy)tripheneylene (2) was designed and synthesized as a π-conjugated platform to produce its tris(cationic radical) derivative (1) in a non-Kekulé and nondisjoint fashion. An electrochemical study revealed the chemically reversible redox property of 2. Gaseous antimony pentachloride-doping of 2 dispersed in a polystyrene matrix gave its cationic radical. It was chemically stable with a half-life >2 weeks and displayed a triplet ground state based on an ESR measurement. A high-spin state with S = 3/2 for 1 was proved by the magnetization and magnetic susceptibility.

KW - π-Conjugated molecule

KW - Arylthiophene

KW - Ferromagnetic interaction

KW - Non-Kekulé molecule

KW - Triphenylene

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2,6,10-Tris(bithiophenyl)triphenylene: Synthesis and high-spin alignment in its p-doped radical derivative

Abstract

Keywords

ASJC Scopus subject areas

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