Synthesis of poly(aryl ether)s bearing phosphonated side-chains from phosphonate ester-containing bisphenols

Abstract

As part of our project research to design aromatic polymers with pendant acid groups, we have paid efforts to synthesize phosphonic acid-containing poly(aryl ether)s (PAEs) from functionalized monomers. To this end, two bisphenol monomers bearing phosphonic ester groups were synthesized. A study of the polymerization reaction via model compound preparation point out specific experimental conditions to prevent side reactions between phosphonic ester functions and phenolate monomers. Based on these experimental optimised conditions, different PAEs with high molecular weights were prepared. Free acid phosphonic groups-containing PAE were obtained by subsequent controlled hydrolysis of phosphonate ester groups.

Impedimetric sensors based on diethylphosphonate‐containing poly(arylene ether nitrile)s films for the detection of lead ions

“…The chemical structure of the resulting polymers was analyzed by NMR spectroscopy. Whereas P1–P6 spectra were reported elsewhere, 19 typical spectra for P7–P9 are reported in supporting information (S6). As an example, the 1 H NMR characterization of both structures containing 40% of phosphonate ester‐containing monomer (P4 (60M a /40M b1 ) and P9 (60M a /40 M b2 )) are reported in Figure 5.…”

“…Diethylphosphonate‐containing bisphenols (compounds 1 and 2) were preliminary prepared, according to multi‐step syntheses, as represented in Figures 1 and 2. Bisphenol 1 procedure was detailed elsewhere 19 …”

“…In the frame of ongoing research work related to the development of new aromatic macromolecular structures, we recently published new insights for the synthesis of phosphonate ester containing poly(arylether)s 19 . Such polymers are readily soluble in common organic solvent, and can be casted into thin films, as required for the preparation of sensors.…”

“…In the frame of ongoing research work related to the development of new aromatic macromolecular structures, we recently published new insights for the synthesis of phosphonate ester containing poly(arylether)s. 19 Such polymers are readily soluble in common organic solvent, and can be casted into thin films, as required for the preparation of sensors. Our expertise in the synthesis of these polymers and recent interesting work concerning the chelation properties of phosphonate ester groups towards lanthanides, 20 prompted us to evaluate their chelating properties towards heavy metal ions, and in particular lead ions.…”

Alkali-Stable Anion Exchange Membranes Based on Poly(xanthene)

“…The bromoalkylated trifluoroacetophenone monomer [1bromo-3-(trifluoroacetylphenyl)-propane, TFAp-Br] was synthesized in high yield (92%) via a one-step Friedel−Crafts trifluoroacylation of 1-bromo-3-phenylpropane using trifluoroacetic anhydride (employing a modified previously published procedure 25 ). The structure of the product was confirmed by 1 H, 13 C, and 19 F NMR spectroscopy (Figure S1, detailed synthetic procedure and NMR analysis are presented as Supporting Information).…”