Preparation and redox properties of fluorinated 1,3-diphenylisobenzofurans

Eleven fluorinated 1,3-diphenylisobenzofurans, materials that are promising to perform efficient singlet fission, have been synthesized and their electrochemical reduction and oxidation in non-aqueous dimethylformamide examined. The redox properties are not changed continuously with increasing numbe...

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Bibliographic Details
Published in:Electrochimica acta 2019-10, Vol.321 (C), p.134659, Article 134659
Main Authors: Kaleta, Jiří, Šimková, Ludmila, Liška, Alan, Bím, Daniel, Madridejos, Jenica M.L., Pohl, Radek, Rulíšek, Lubomír, Michl, Josef, Ludvík, Jiří
Format: Article
Language:English
Subjects:
Chemical reduction
DFT calculations
Fluorinated 1,3-Diphenylisobenzofurans
Fluorination
Fluorine
Mathematical analysis
Oxidation
Oxidation/reduction
Singlet fission
Synthesis
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Summary:Eleven fluorinated 1,3-diphenylisobenzofurans, materials that are promising to perform efficient singlet fission, have been synthesized and their electrochemical reduction and oxidation in non-aqueous dimethylformamide examined. The redox properties are not changed continuously with increasing number of fluorine substituents but there are some qualitative turns in behavior for specific types of substitution revealing a discontinuity requiring deeper investigation. The DFT calculations confirm the trends observed experimentally by correlation of experimental and calculated data. The differences between the geometries of the neutral species and their radical ions were computed and rationalized. [Display omitted]
ISSN:0013-4686
1873-3859
DOI:10.1016/j.electacta.2019.134659