The anodic reactivity of 4,4′-dimethoxychalcone: a synthetic and mechanistic investigation

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• 作者：Imen Aribi ; Sahbi Ayachi ; Kamel Alimi ; Sadok Roudesli…
• 关键词：Anodic oxidation ; Chalcone ; Radical cation ; Conjugated oligomers ; Photoluminescence
• 刊名：Research on Chemical Intermediates
• 出版年：2017
• 出版时间：January 2017
• 年：2017
• 卷：43
• 期：1
• 页码：73-89
• 全文大小：
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Catalysis; Physical Chemistry; Inorganic Chemistry;
• 出版者：Springer Netherlands
• ISSN：1568-5675
• 卷排序：43

文摘

The anodic oxidation of the 4,4′-dimethoxychalcone (DMC) was investigated by different electrochemical methods at a platinum working electrode and in acetonitrile as a solvent. The DMC exhibited a single irreversible anodic peak around 1.6 V versus Ag/AgCl. On the time scale of cyclic voltammetry experiments, the highly reactive radical cation issued from the first electron transfer underwent a second order rate-limiting reaction. The potential imposed electrolyses of DMC led to the formation of a semi-conducting oligomer with 40 % yield. Using different physico-chemicals methods, the structural study confirmed the formation of an o-phenylenevinylene oligomer. The values of the corresponding optical and electrochemical band gaps were calculated to be 3.15 and 2.86 eV, respectively. Finally, a mechanism for the DMC electro-oligomerization was proposed on the basis of the obtained results.