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Organoboron Compounds as Lewis Acid Receptors of Fluoride Ions in Polymeric Membranes

Organoboron Compounds as Lewis Acid Receptors of Fluoride Ions in Polymeric Membranes

Martyna Jańczyk, Agnieszka Adamczyk-Woźniak, Andrzej Sporzyński, Wojciech Wróblewski

Anal Chim Acta. 2012 Jul 6;733:71-7.

PMID: 22704378

Abstract:

Newly synthesized organoboron compounds - 4-octyloxyphenylboronic acid (OPBA) and pinacol ester of 2,4,6-trifluorophenylboronic acid (PE-PBA) - were applied as Lewis acid receptors of fluoride anions. Despite enhanced selectivity, the polymer membrane electrodes containing the lipophilic receptor OPBA exhibited non-Nernstian slopes of the responses toward fluoride ions in acidic conditions. Such behavior was explained by the lability of the B-O bond in the boronic acids, and the OH(-)/F(-) exchange at higher fluoride content in the sample solution. In consequence, the stoichiometry of the OPBA-fluoride complexes in the membrane could vary during the calibration, changing the equilibrium concentration of the primary anion in membrane and providing super-Nernstian responses. The proposed mechanism was supported by (19)F NMR studies, which indicated that the fluoride complexation proceeds more effectively in acidic solution leading mainly to PhBF(3)(-) species. Finally, the performances of the membranes based on the phenylboronic acid pinacol ester, with a more stable B-O bond, were tested. As it was expected, Nernstian fluoride responses were recorded for such membranes with worsened fluoride selectivity.

Chemicals Related in the Paper:

Catalog Number	Product Name	CAS Number	Price
AP247564712	2,3,6-Trifluorophenylboronic acid	247564-71-2	Price
AP871125701	3-Propoxy-2,4,6-trifluorophenylboronic acid	871125-70-1	Price
LS793292	3-(4-Methylpiperazine-1-carbonyl)phenylboronic acid, pinacol ester		Price

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