Fluorinated allyl-, acetyl-, and bromo-containing hydroxyl-substituted phenyl ethers with a hexafluorobenzene or decafluorobiphenyl central unit

We report on methods of synthesis of new hexafluorobenzene- and decafluorobiphenyl-based hydroxyl-substituted phenyl ethers containing allyl, acetyl groups, and bromine atoms. Optimal conditions for Claisen and Fries rearrangements used during the synthesis of these fluorinated compounds are discussed. The resulting compounds can be employed as monomers for synthesis of a wide variety of nucleus-fluorinated aromatic polymers suitable for optical or membrane applications.

Graphical abstractWe report for the first time on the synthesis of two sets of functional fluorinated monomers based on 4-[2,3,5,6-tetrafluoro-4-(4-hydroxyphenoxy)phenoxy]phenol or 4-{2,3,5,6-tetrafluoro-4-[2,3,5,6-tetrafluoro-4-(4-hydroxyphenoxy)phenyl]phenoxy}phenol units and containing allyl, acetyl groups, and bromine atoms. Synthesis of such novel compounds became possible under application of the Claisen or Fries rearrangements as well as bromination reaction. The compounds were characterized by IR, (1H, 19F, and 13C) NMR spectroscopy and mass spectrometry techniques.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Novel allyl-, acetyl-, and bromo-containing monomers with a hexafluorobenzene or decafluorobiphenyl fragments were synthesized. ► Optimal conditions for Claisen and Fries rearrangements were found and described. ► The ability of the synthesized compounds to form hydrogen bonds was investigated. ► The synthesized compounds can be used as monomers for synthesis of nucleus-fluorinated aromatic polymers with various functional groups.