Synthesis, Properties and Redox Behavior of Ene-Diyne Scaffolds Bearing 1- and 2-Azulenyl Groups at the Periphery

被引：18

作者：

Shoji, Taku ^{[1
]}

Shimomura, Erika ^{[1
]}

Maruyama, Mitsuhisa ^{[1
]}

Ito, Shunji ^{[2
]}

Okujima, Tetsuo ^{[3
]}

Morita, Noboru ^{[4
]}

机构：

[1] Shinshu Univ, Fac Sch Sci, Dept Chem, 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：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2013卷 / 05期

关键词：

Azulene; Conjugation; Redox chemistry; Synthetic methods; Cyclic voltammetry; PUSH-PULL CHROMOPHORES; VIOLENE/CYANINE HYBRIDS; ELECTROCHROMIC SYSTEMS; BENZENE-RING; BIS; DERIVATIVES; DICATIONS; MONO; 2,5-THIOPHENEDIYL; STABILITIES;

D O I：

10.1002/ejoc.201201397

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ene-diyne systems possessing 1- and 2-azulenyl groups at the periphery were prepared by palladium-catalyzed cross-coupling reaction of 1- and 2-ethynylazulenes with 9-di-bromomethylene-9H-fluorene and 9,10-bis(dibromomethylene)-9,10-dihydroanthracene or 2-iodoazulene with 9,10-bis(diethynylmethylene)-9,10-dihydroanthracene under Sonogashira-Hagihara conditions. The redox behavior of the ene-diyne compounds was examined by cyclic voltammetry (CV) and differential pulse voltammetry (DPV). Moreover, a significant color change of the ene-diyne derivatives was observed with visible spectroscopy under electrochemical reduction conditions.

引用

页码：957 / 964

页数：8

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