Boronic acid-containing polyanilines

Boronic acid-containing polyaniline has also been utilized in diabetes-related research. One such polymer (23) (Fig. 17) has been observed to exhibit a linear near-infrared optical response to saccharides.43 The polymer was prepared by the copolymerization of aniline with 3-aminophenylboronic acid using lOmM (NH4)S208 in 1M HC1. The films were observed to undergo changes in the absorption spectra on addition of saccharides at pH 7.2. 

Figure 17 Boronic acid-containing polyanilines (23 and 24) used in the detection of saccharides. (Adapted from refs. 43 and 44.)...

Similarly, self-doped PABA can be prepared using excess of saccharide and one equivalent of fluoride to monomer. Complexation between saccharides and aromatic boronic acids is highly pH dependent, presumably due to the tetrahedral intermediate involved in complexation [25]. Because the pKa of 3-aminophenylboronic acid is 8.75, complexation requires pH values above 8.6. This pH range is not compatible with the electrochemical synthesis of polyaniline, which is typically carried out near a pH value of 0. However, Smith et al. have shown that the addition of fluoride can stabilize the complexation of molecules containing vicinal diols with aromatic boronic acids [23]. Based on this work, it was postulated that the electrochemical polymerization of a saccharide complex with 3-aminophenylboronic acid in the presence of one molar equivalent of fluoride at pH values lower than 8 is possible if a self-doped polymer is produced in the process. 

Some measurements of this property have been made in a range of electrically conducting polymers. These include epoxy resin/polyaniline-dodecylbenzene sulfonic acid blends [38], polystyrene-black polyphenylene oxide copolymers [38], semiconductor-based polypyrroles [33], titanocene polyesters [40], boron-containing polyvinyl alcohol [41], copper-filled epoxy resin [42], polyethylidene dioxy thiophene-polystyrene sulfonate, polyvinyl chloride, polyethylene oxide [43], polycarbonate/acrylonitrile-butadiene-styrene composites [44], polyethylene oxide complexes with sodium lanthanum tetra-fluoride [45], chlorine-substituted polyaniline [46], polyvinyl pyrolidine-polyvinyl alcohol coupled with potassium bromate tetrafluoromethane sulfonamide [47], doped polystyrene block polyethylene [38, 39], polypyrrole [48], polyaniline-polyamide composites [49], and polydimethyl siloxane-polypyrrole composites [50]. 

Electrical properties have been reported on numerous carbon fiber-reinforced polymers, including carbon nanoflber-modified thermotropic liquid crystalline polymers [53], low-density polyethylene [54], ethylene vinyl acetate [55], wire coating varnishes [56], polydimethyl siloxane polypyrrole composites [50], polyacrylonitrile [59], polycarbonate [58], polyacrylonitrile-polycarbonate composites [58], modified chrome polymers [59], lithium trifluoromethane sulfonamide-doped polystyrene-block copolymer [60], boron-containing polyvinyl alcohols [71], lanthanum tetrafluoride complexed ethylene oxide [151, 72, 73], polycarbonate-acrylonitrile diene [44], polyethylene deoxythiophe-nel, blends of polystyrene sulfonate, polyvinyl chloride and polyethylene oxide [43], poly-pyrrole [61], polypyrrole-polypropylene-montmorillonite composites [62], polydimethyl siloxane-polypyrrole composites [63], polyaniline [46], epoxy resin-polyaniline dodecyl benzene sulfonic acid blends [64], and polyaniline-polyamide 6 composites [49]. 

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