Synthesis of 2-Azulenyltetrathiafulvalenes by Palladium-Catalyzed Direct Arylation of 2-Chloroazulenes with Tetrathiafulvalene and Their Optical and Electrochemical Properties

被引：27

作者：

Shoji, Taku ^{[1
]}

Araki, Takanori ^{[1
]}

Sugiyama, Shuhei ^{[1
]}

Ohta, Akira ^{[1
]}

Sekiguchi, Ryuta ^{[2
]}

Ito, Shunji ^{[2
]}

Okujima, Tetsuo ^{[3
]}

Toyota, Kozo ^{[4
]}

机构：

[1] Shinshu Univ, Grad Sch Sci & Technol, Matsumoto, Nagano 3908621, Japan

[2] Hirosaki Univ, Grad Sch Sci & Technol, Hirosaki, Aomori 0368561, Japan

[3] Ehime Univ, Grad Sch Sci & Engn, Dept Biol & Chem, Matsuyama, Ehime 7908577, Japan

[4] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 03期

关键词：

CROSS-COUPLING REACTION; LIQUID-CRYSTALLINE BEHAVIOR; 1ST ORGANOTIN REAGENTS; 2+2 CYCLOADDITION; REDOX BEHAVIOR; CONJUGATED POLYMERS; ARYL BROMIDES; AZULENE RING; EASY ACCESS; BEARING;

D O I：

10.1021/acs.joc.6b02818

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tetrathiafulvalene (TTF) derivatives with 2-azulenyl substituents 5-11 were prepared by the palladium catalyzed direct arylation reaction of 2-chloroazulenes with TTF in good yield. Photophysical properties of these compounds were investigated by UV-vis spectroscopy and theoretical calculations. Redox behavior of the novel azulenesubstituted TTFs was examined by using cyclic voltammetry and differential pulse voltammetry, which revealed their multistep electrochemical oxidation and/or reduction properties. Moreover, these TTF derivatives showed significant spectral change in the visible region under the redox conditions.

引用

收藏

页码：1657 / 1665

页数：9

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