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Synthesis, cyclic voltammetry, and UV–Vis studies of ferrocene-dithiafulvalenes as anticipated electron-donor materials

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Abstract

New ferrocenyl ketones were obtained as precursors of novel π-conjugated ferrocene-dithiafulvalene (Fc-DTF) and π-extended-ferrocenedithia-fulvalenes (π-exFc-DTF) as electron-donor conducting materials from ferrocene by a direct aroylation process using the Friedel–Crafts reaction. Novel Fc-DTF conjugates were synthesized using the Wittig–Horner reaction and their structures were determined. The redox behavior of the ferrocenyl carbonyl compounds Fc-DTF and Fc-π-exDTF was investigated in comparison to the parent ferrocene by means of cyclic voltammetry. A one-electron redox behavior was observed for carbonylferrocenes as one wave potential, while a two-electron process was observed as two oxidation waves for the conjugates. Introduction of electron-withdrawing groups led to increasing E pa values and decreasing ΔE p values. The UV–Vis spectra of some compounds were studied in comparison with ferrocene. The absorption spectra showed a red-shift with a slight increase in the absorption intensities.

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Acknowledgments

The authors wish to thank the Scientific Research and the Ministry of Education, Sciences, Sports and Culture (Japan) and Assiut University (Egypt) for supporting this work.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Assiut University, Assiut, 71516, Egypt

    Abdelwareth A. O. Sarhan, Mohammed S. Ibrahim & Mostafa M. Kamal

  2. Department of Chemistry and Chemical Engineering, Faculty of Engineering, Yamagata University, 3-16 Jonan-4-Chome, Yonezawa, 992-8510, Japan

    Kaiko Mitobe & Taeko Izumi

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  1. Abdelwareth A. O. Sarhan
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  2. Mohammed S. Ibrahim
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  3. Mostafa M. Kamal
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Correspondence to Abdelwareth A. O. Sarhan.

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Sarhan, A.A.O., Ibrahim, M.S., Kamal, M.M. et al. Synthesis, cyclic voltammetry, and UV–Vis studies of ferrocene-dithiafulvalenes as anticipated electron-donor materials. Monatsh Chem 140, 315–323 (2009). https://doi.org/10.1007/s00706-008-0025-2

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