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. The differences between the geometries of the neutral species and their radical ions were computed and rationalized.