| Summary: | Phenylboronic acid-bearing polyamidoamine dendrimer (PBA-PAMAM)/poly(vinyl alcohol) (PVA) multilayer films were prepared through the layer-by-layer (LbL) deposition of PBA-PAMAM solution and PVA solution. PBA-PAMAM/PVA films were constructed successfully through the formation of boronate ester bonds between the boronic acid moiety in PBA and 1,3-diol units in PVA. When the (PBA-PAMAM/PVA)<sub>5</sub> films were immersed in rose bengal (RB) solution, RB was adsorbed onto the LbL films. The amount of RB adsorbed was higher in the LbL films immersed in acidic solution than in basic solution. The release of RB from the LbL films was also promoted in the basic solution, while it was suppressed in the acidic solution. The boronic acid ester is oxidized to phenol by hydrogen peroxide (H<sub>2</sub>O<sub>2</sub>) and the carbon-boron bond is cleaved, so that the (PBA-PAMAM/PVA)<sub>5</sub> films can be decomposed by immersion in H<sub>2</sub>O<sub>2</sub> solution. Therefore, when RB-adsorbed (PBA-PAMAM/PVA)<sub>5</sub> films were immersed in H<sub>2</sub>O<sub>2</sub> solution, the release of RB was moderately promoted when the solution was weakly acidic.
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