Synthesis of A Novel exTTF Derivative and Its Electron Transfer towards p-Chloranil

doi:10.6023/cjoc201312004

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (7): 1417-1423.DOI: 10.6023/cjoc201312004 Previous Articles Next Articles

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新型exTTF衍生物的合成及其与四氯对苯醌的电子转移

赵邦屯^a, 陈秀华^b, 李佳佳^b, 朱卫民^b

a 洛阳师范学院化学化工学院洛阳 471022;
b 郑州大学化学与分子工程学院郑州 450010

收稿日期:2013-12-03 修回日期:2014-01-20 发布日期:2014-03-14
通讯作者: 赵邦屯, 朱卫民 E-mail:zbt@lynu.edu.cn;zhuwm@zzu.edu.cn
基金资助:
国家自然科学基金（Nos.21172105，20872058）资助项目.

Synthesis of A Novel exTTF Derivative and Its Electron Transfer towards p-Chloranil

Zhao Bangtun^a, Chen Xiuhua^b, Li Jiajia^b, Zhu Weimin^b

a College of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471022;
b College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001

Received:2013-12-03 Revised:2014-01-20 Published:2014-03-14
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21172105, 20872058)

1. Synthesis of A Novel exTTF Derivative and Its Electron Transfer towards p-Chloranil.PDF(714KB)

Abstract

Using anthraquinone and 1,3-dithiol-2-thiones (1 and 3) as starting materials, the exTTF compound 9-[4,5- bis((2-cyanoethyl)thio)-1,3-dithiol-2-ylidene]-10-[4,5-(ethylenedithio)-1,3-dithiol-2-ylidene]-9,10-dihydroanthracene (4) was prepared by tripmethyl phosphite-induced Wittig cross-coupling reaction. In the presence of cesium hydroxide, the exTTF 4 was reacted with 2-(chloroethoxy)ethanol to obtain the exTTF compound 9-[4-[(2-cyanoethyl)-5-[(2-(2-hydroxyethoxy)- ethyl)thio]-1,3-dithiol-2-ylidene]-10-[4,5-(ethylenedithio)-1,3-dithiol-2-ylidene]-9,10-dihydroathracene (5) in 76% yield. The target exTTF compound 9-[4-[(2-cyanoethyl)-5-[(2-(2-(4-nitrophenoxy)ethoxy)ethyl)thio]-1,3-dithiol-2-ylidene]-10-[4,5- (ethylenedithio)-1,3-ditiol-2-ylidene]-9,10-dihydroanthracene (6) was obtained by Mitsunobu reaction of 5 and p-nitrophenol using diethyl azodicarboxy/triphenylphosphine (DEAD/PPh₃) system in 24% yield. Meanwhile, the structure of exTTF 4 was identified by X-ray diffraction analysis. The cyclic voltammogramsed showed that the compound 6 displayed two-electron quasi-reversible redox processes. Moreover, the UV-Vis absorption studies show that intermolecular electron transfer between exTTF 6 and p-chloranil may be promoted by specific metal ions such as Sc³⁺, Al³⁺ and Pb²⁺.

Key words: exTTF, crystal structure, p-chloranil, electron transfer

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Zhao Bangtun, Chen Xiuhua, Li Jiajia, Zhu Weimin. Synthesis of A Novel exTTF Derivative and Its Electron Transfer towards p-Chloranil[J]. Chin. J. Org. Chem., 2014, 34(7): 1417-1423.

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新型exTTF衍生物的合成及其与四氯对苯醌的电子转移

Synthesis of A Novel exTTF Derivative and Its Electron Transfer towards p-Chloranil

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