One-step synthesis of perfluorinated polyphenylenes using modified Ullmann coupling conditions

Fluorinated compounds have attracted attention in both the pharmaceutical industry and materials science due to the small size and strong electron-withdrawing property of the fluorine atom. In materials science, perfluorinated polyphenylenes play an important role as electron transport layers in organic electronics. While various strategies for the preparation of fluorinated arenes have been reported, the number of synthetic methods available for perfluorinated arenes remains limited, mainly due to the change in reactivity of reagents and substrates at the reaction site upon the introduction of additional fluorine atoms. Given the important applications of perfluorinated polyphenyl-based compounds, this article describes the one-step synthesis of the dendrimer perfluoro-3,3'5,5'-tetrakisphenyldiphenyl-1,1', which to date no example of a targeted synthesis has been reported in literature, and the synthetic methodology for the direct preparation of linear perfluorinated para-sexiphenyl. Both strategies use starting materials that are either commercially available or can be easily accessed using standard literature methods.

Automated summary

Fluorinated compounds have gained attention for their small size and strong electron-withdrawing property. In materials science, perfluorinated polyphenylenes are important in organic electronics as electron transport layers. However, the synthesis of perfluorinated arenes is limited due to changes in reactivity upon the introduction of additional fluorine atoms. This article describes the one-step synthesis of a dendrimer perfluoro-3,3'5,5'-tetrakisphenyldiphenyl-1,1' and the synthetic methodology for the direct preparation of linear perfluorinated para-sexiphenyl, using commercially available or easily accessible starting materials.