Trifluoromethylation of carbonyl groups in aromatic poly(ether ketone)s: formation of strongly polar yet surface-hydrophobic poly(arylenenecarbinol)s

Leroux, F., Bennett, R. ORCID: https://orcid.org/0000-0001-6266-3510, Lewis, D. and Colquhoun, H. M. (2018) Trifluoromethylation of carbonyl groups in aromatic poly(ether ketone)s: formation of strongly polar yet surface-hydrophobic poly(arylenenecarbinol)s. Macromolecules, 51 (9). pp. 3415-3422. ISSN 0024-9297 doi: 10.1021/acs.macromol.8b00017

Abstract/Summary

Fluoride-catalyzed reactions of trimethyl(trifluoromethyl)silane with a range of aromatic poly(ether ketone)s, both amorphous and semi-crystalline, proceed quantitatively in THF to yield soluble, amorphous polymers in which the carbon-silicon bond of CF3SiMe3 has added across the carbonyl-oxygen double bond of each carbonyl group. When the starting poly(ether ketone) is amorphous and soluble in THF the reaction is fairly rapid (hours), but is much slower (days) when the starting polymer is semi-crystalline, with only low solubility in THF. Quantitative desilylation of the resulting polymers is achieved by reaction with excess fluoride ion, affording poly(arylene-trifluoromethylcarbinol)s. These extremely polar polymers are readily soluble in protic solvents such as methanol or ethanol, to give solutions from which tough, coherent films may be cast by evaporation in air. Despite the evidently high polarity of the bulk polymers, the surfaces of cast films are relatively hydrophobic, with static water contact angles of ~ 90°. Surface analyses by XPS are consistent with enrichment of the polymer-air interface in CF3 groups.

Item Type	Article
URI	https://reading-clone.eprints-hosting.org/id/eprint/77256
Item Type	Article
Refereed	Yes
Divisions	Interdisciplinary centres and themes > Chemical Analysis Facility (CAF) Life Sciences > School of Chemistry, Food and Pharmacy > Department of Chemistry Interdisciplinary centres and themes > Chemical Analysis Facility (CAF) > NMR (CAF) Interdisciplinary centres and themes > Chemical Analysis Facility (CAF) > Optical Spectroscopy (CAF) Interdisciplinary centres and themes > Chemical Analysis Facility (CAF) > Thermal Analysis (CAF)
Publisher	American Chemical Society
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