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

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:
 [1];  [2];  [2];  [2];  [2];  [2];  [2];  [1];  [2]
  1. Czech Academy of Sciences, Prague (Czech Republic); Univ. of Colorado, Boulder, CO (United States)
  2. Czech Academy of Sciences, Prague (Czech Republic)
Publication Date:
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.
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. doi:https://doi.org/10.1016/j.electacta.2019.134659
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. doi:https://doi.org/10.1016/j.electacta.2019.134659. https://www.osti.gov/servlets/purl/1688398.
@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 = {2019},
month = {8}
}