Chinese Journal of Organic Chemistry >
Synthesis of A Novel exTTF Derivative and Its Electron Transfer towards p-Chloranil
Received date: 2013-12-03
Revised date: 2014-01-20
Online published: 2014-03-14
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21172105, 20872058)
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
Zhao Bangtun , Chen Xiuhua , Li Jiajia , Zhu Weimin . Synthesis of A Novel exTTF Derivative and Its Electron Transfer towards p-Chloranil[J]. Chinese Journal of Organic Chemistry, 2014 , 34(7) : 1417 -1423 . DOI: 10.6023/cjoc201312004
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