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

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Abstract

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.

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Acknowledgments

This research was supported by the Ministry of Higher Education and Scientific Research, Tunisia. Authors are grateful to Mr Adel Rdissi for English revision.

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Authors and Affiliations

  1. Laboratoire Interfaces et Matériaux Avancés, Faculté des Sciences de Monastir, Université de Monastir, 5000, Monastir, Tunisia

    Imen Aribi, Sadok Roudesli & Ayoub Haj Said

  2. Unité de Recherche (UR 11ES55), Matériaux Nouveaux et Dispositifs Electroniques Organiques, Faculté des Sciences de Monastir, Université de Monastir, 5000, Monastir, Tunisia

    Sahbi Ayachi & Kamel Alimi

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  1. Imen Aribi
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Correspondence to Ayoub Haj Said.

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Aribi, I., Ayachi, S., Alimi, K. et al. The anodic reactivity of 4,4′-dimethoxychalcone: a synthetic and mechanistic investigation. Res Chem Intermed 43, 73–89 (2017). https://doi.org/10.1007/s11164-016-2607-7

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