Quinone dimers connected by 1,4-phenylene and 2,5-thienylene moieties as a π-linker

Naoto Hayashi; Teru Sakakibara; Takahiro Ohnuma; Junro Yoshino; Hiroyuki Higuchi

doi:10.3987/COM-09-S(S)108

Quinone dimers connected by 1,4-phenylene and 2,5-thienylene moieties as a π-linker

Naoto Hayashi^*, Teru Sakakibara, Takahiro Ohnuma, Junro Yoshino, Hiroyuki Higuchi

^*Corresponding author for this work

Department of Chemistry

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

4 Scopus citations

Abstract

The synthesis and characterization of quinone dimers connected by 1,4-phenylene (QPQ) and 2,5-thienylene (QTQ) linkers are described. QPQ and QTQ were synthesized by means of Suzuki coupling and subsequent oxidation. Significant bathochromic shifts were observed in the electronic absorption spectra of QPQ and QTQ as compared to that of the quinine dimers without a linker. In addition, cyclic voltammetry and DFT calculations demonstrated that QTQ was a stronger electron acceptor than QPQ due to its planar structure, even though QTQ contains an electron-rich thiophene ring.

Original language	English
Pages (from-to)	1227-1238
Number of pages	12
Journal	Heterocycles
Volume	80
Issue number	2
DOIs	https://doi.org/10.3987/COM-09-S(S)108
State	Published - 2010/03/01

Keywords

Cyclic Voltammetry
Electronic Absorption Spectra
Quinone
π Linker
π-Conjugation System

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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10.3987/COM-09-S(S)108

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title = "Quinone dimers connected by 1,4-phenylene and 2,5-thienylene moieties as a π-linker",

abstract = "The synthesis and characterization of quinone dimers connected by 1,4-phenylene (QPQ) and 2,5-thienylene (QTQ) linkers are described. QPQ and QTQ were synthesized by means of Suzuki coupling and subsequent oxidation. Significant bathochromic shifts were observed in the electronic absorption spectra of QPQ and QTQ as compared to that of the quinine dimers without a linker. In addition, cyclic voltammetry and DFT calculations demonstrated that QTQ was a stronger electron acceptor than QPQ due to its planar structure, even though QTQ contains an electron-rich thiophene ring.",

keywords = "Cyclic Voltammetry, Electronic Absorption Spectra, Quinone, π Linker, π-Conjugation System",

author = "Naoto Hayashi and Teru Sakakibara and Takahiro Ohnuma and Junro Yoshino and Hiroyuki Higuchi",

year = "2010",

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T1 - Quinone dimers connected by 1,4-phenylene and 2,5-thienylene moieties as a π-linker

AU - Hayashi, Naoto

AU - Sakakibara, Teru

AU - Ohnuma, Takahiro

AU - Yoshino, Junro

AU - Higuchi, Hiroyuki

PY - 2010/3/1

Y1 - 2010/3/1

N2 - The synthesis and characterization of quinone dimers connected by 1,4-phenylene (QPQ) and 2,5-thienylene (QTQ) linkers are described. QPQ and QTQ were synthesized by means of Suzuki coupling and subsequent oxidation. Significant bathochromic shifts were observed in the electronic absorption spectra of QPQ and QTQ as compared to that of the quinine dimers without a linker. In addition, cyclic voltammetry and DFT calculations demonstrated that QTQ was a stronger electron acceptor than QPQ due to its planar structure, even though QTQ contains an electron-rich thiophene ring.

AB - The synthesis and characterization of quinone dimers connected by 1,4-phenylene (QPQ) and 2,5-thienylene (QTQ) linkers are described. QPQ and QTQ were synthesized by means of Suzuki coupling and subsequent oxidation. Significant bathochromic shifts were observed in the electronic absorption spectra of QPQ and QTQ as compared to that of the quinine dimers without a linker. In addition, cyclic voltammetry and DFT calculations demonstrated that QTQ was a stronger electron acceptor than QPQ due to its planar structure, even though QTQ contains an electron-rich thiophene ring.

KW - Cyclic Voltammetry

KW - Electronic Absorption Spectra

KW - Quinone

KW - π Linker

KW - π-Conjugation System

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U2 - 10.3987/COM-09-S(S)108

DO - 10.3987/COM-09-S(S)108

M3 - 学術論文

AN - SCOPUS:77955688252

SN - 0385-5414

VL - 80

SP - 1227

EP - 1238

JO - Heterocycles

JF - Heterocycles

IS - 2

ER -

Quinone dimers connected by 1,4-phenylene and 2,5-thienylene moieties as a π-linker

Abstract

Keywords

ASJC Scopus subject areas

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