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We report on the chemical polymerization of 2-methoxyaniline at the interface between an aqueous solution and air. The polymer is formed in the interfacial region, whereas the soluble trimer is yielded in the bulk of the polymerization solution. The preferential polymerization of 2-methoxyaniline is discussed in terms of monomer and oligomer accumulation at the interface, which influences the reactivity of these species and allows further polymerization. The phenomenon of polymer growth is employed to selectively deposit polymeric material onto glass slides decorated with gas microbubbles. Because of preferential polymerization at the bubble/solution interface, hemispherical features are produced on the surface of glass. When some polymeric material is mechanically removed, microrings or microholes are obtained. The anomalous polymerization of 2-methoxyaniline is compared to that of 2-methylaniline. This monomer polymerizes uniformly within the entire volume of the reaction mixture; thus, no preferential polymer formation at the gas/solution interface is observed. As a result, deposition on microbubble-decorated glass slides produces polymeric films containing a number of microholes.

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