Preparation and redox properties of fluorinated 1,3-diphenylisobenzofurans

Kaleta, Jiří; Šimková, Ludmila; Liška, Alan; Bím, Daniel; Madridejos, Jenica M. L.; Pohl, Radek; Rulíšek, Lubomír; Michl, Josef; Ludvík, Jiří

doi:10.1016/j.electacta.2019.134659

Title: Preparation and redox properties of fluorinated 1,3-diphenylisobenzofurans

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Abstract

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. In conclusion, the differences between the geometries of the neutral species and their radical ions were computed and rationalized.

Authors:

Kaleta, Jiří ^[1]; Šimková, Ludmila ^[2]; Liška, Alan ^[2]; Bím, Daniel ^[2]; Madridejos, Jenica M. L. ^[2]; Pohl, Radek ^[2]; Rulíšek, Lubomír ^[2]; Michl, Josef ^[1]; Ludvík, Jiří ^[2]

Czech Academy of Sciences, Prague (Czech Republic); Univ. of Colorado, Boulder, CO (United States)
Czech Academy of Sciences, Prague (Czech Republic)

Publication Date:: Fri Aug 09 00:00:00 EDT 2019

Research Org.:: Univ. of Colorado, Boulder, CO (United States)

Sponsoring Org.:: USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division; USDOE

OSTI Identifier:: 1688398

Alternate Identifier(s):: OSTI ID: 1564546

Grant/Contract Number:: SC0007004

Resource Type:: Accepted Manuscript

Journal Name:: Electrochimica Acta

Additional Journal Information:: Journal Volume: 321; Journal ID: ISSN 0013-4686

Publisher:: Elsevier

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; Fluorinated 1,3-Diphenylisobenzofurans; Singlet fission; Synthesis; Oxidation/reduction; DFT calculations

Citation Formats


                    Kaleta, Jiří, Šimková, Ludmila, Liška, Alan, Bím, Daniel, Madridejos, Jenica M. L., Pohl, Radek, Rulíšek, Lubomír, Michl, Josef, and Ludvík, Jiří. Preparation and redox properties of fluorinated 1,3-diphenylisobenzofurans.  United States: N. p., 2019. 
Web.  doi:10.1016/j.electacta.2019.134659.

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                    Kaleta, Jiří, Šimková, Ludmila, Liška, Alan, Bím, Daniel, Madridejos, Jenica M. L., Pohl, Radek, Rulíšek, Lubomír, Michl, Josef, & Ludvík, Jiří. Preparation and redox properties of fluorinated 1,3-diphenylisobenzofurans.  United States.  https://doi.org/10.1016/j.electacta.2019.134659

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                    Kaleta, Jiří, Šimková, Ludmila, Liška, Alan, Bím, Daniel, Madridejos, Jenica M. L., Pohl, Radek, Rulíšek, Lubomír, Michl, Josef, and Ludvík, Jiří. Fri .  
"Preparation and redox properties of fluorinated 1,3-diphenylisobenzofurans".  United States.  https://doi.org/10.1016/j.electacta.2019.134659.  https://www.osti.gov/servlets/purl/1688398.

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@article{osti_1688398,

  title        = {Preparation and redox properties of fluorinated 1,3-diphenylisobenzofurans},

  author       = {Kaleta, Jiří and Šimková, Ludmila and Liška, Alan and Bím, Daniel and Madridejos, Jenica M. L. and Pohl, Radek and Rulíšek, Lubomír and Michl, Josef and Ludvík, Jiří},

  abstractNote = {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. In conclusion, the differences between the geometries of the neutral species and their radical ions were computed and rationalized.},

  doi          = {10.1016/j.electacta.2019.134659},

  journal      = {Electrochimica Acta},

  number       = ,

  volume       = 321,

  place        = {United States},

  year         = {Fri Aug 09 00:00:00 EDT 2019},

  month        = {Fri Aug 09 00:00:00 EDT 2019}

}

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