Polypyrrole , boronate-functionalized

In the area of ion sensing, cation recognition by electrodes containing functionalized redox-active polymers has been an area of considerable interest. Fabre and co-workers have reported the development of a boronate-functionalized polypyrrole as a fluoride anion-responsive electroactive polymer film. The electropolymerizable polypyrrole precursor (11) (Fig. 11) was synthesized by the hydroboration reaction of l-(phenylsulfonyl)-3-vinylpyrrole with diisopinocampheylborane followed by treatment with pinacol and the deprotection of the pyrrole ring.33 The same methodology was utilized for the production of several electropolymerizable aromatic compounds (of pyrrole (12) (Fig. 11), thiophene (13 and 14) (Fig. 11), and aniline) bearing boronic acid and boronate substituents as precursors of fluoride- and/or chloride-responsive conjugated polymer.34... 

Using a different approach, the research gronps of Fabre and Freund have synthesized boronate-functionalized conjugated polymers, which serve as electrochemical sensors. For example, a conjugated redox-active film of polypyrrole (174) was electrodeposited onto a platinum electrode from acetonitrile solution. Addition of fluoride anions led to a new redox system that showed an anodic shift relative to polypyrrole itself, which was attributed to fluoride binding to the boronate group. A related poly(aniline boronic acid) (175) was also reported and studied for saccharide detection. " ... 

Nicolas, M., B. Fabre, and J. Simonet. 1999. Boronate-functionalized polypyrrole as a new fluoride sensing material. Chem Commun 1881-1882. 

The Teixidor team further improved upon this chemistry by covalently linking units of 109 to the polypyrrole monomer prior to electropolymerization.139 A [3,3 -Co(C2B<)H11)2] anion was covalently bound to a pyrrole via a spacer through one of its boron atoms by the reaction of the species [3,3 -Co(8-C4H802-l,2-C2B9H10)(r,2 -(C2B9H11)2] with potassium pyrrole, as functionalization through... 

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