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

Abstract

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.

Graphical Abstract

Keywords:

• Arenes
• perfluorination
• Ullmann coupling

Acknowledgments

The authors would like to thank Benjamin King and Raluchukwu Ewenike for performing the sublimation on the perfluorinated polyphenylenes, and Dr. Matthew W. Forbes at the AIMS Mass Spectrometry Laboratory at the University of Toronto for collecting the mass spectra of our samples.

Disclosure statement

The authors report there are no competing interests to declare.

Additional information

Funding

This work was supported by Canadian Foundation for Innovation and the National Science and Engineering Council of Canada under grant (RGPIN-2021-04146 to J. L. B.).