Synthesis and Properties of Photosensitive Poly(urethane-acrylate) Containing Anil Groups With Application in the Chemosensors Area

Some aspects of the enol-imine to keto-enamine photoisomerism and fluorescent behavior of the new monomer with urethane and anil units in its structure, namely, methacryloyloxyethyl-2-carbamoyloxy(m-methyl, o-hydroxybenziliden)aniline (UAN), were studied comparatively with the corresponding copolymer poly (methacryloyloxyethyl-2-carbamoyloxy(m-methyl, o-hydroxybenziliden)aniline)-co-methyl methacrylate) (COP-UAN). The structure, thermal properties, and morphology of the anil compounds were investigated by Fourier transform infrared, proton nuclear magnetic resonance, fluorescence spectroscopies, UV spectrophotometry, thermogravimetric analysis, differential scanning calorimetry, and atomic force microscopy. The photochromic behavior of salicylideneanil units was investigated by UV/laser irradiation, and an inspection of their photophysical properties suggested that such structures could function as fluorescent chemosensors for some transition metals, a fluorescence quenching in the presence of different metal cations (Fe3+, Fe2+, Cu2+, and Ni2+) being evidenced. The direct observation of an enhancement in the fluorescence emission caused of the presence of Zn2+ (solution) or Fe2+, Cu2+, and Zn2+ (thin film) would be rather suitable for the production of turn-on fluorescent chemosensors. POLYM. ENG. SCI., 2011. © 2011 Society of Plastics Engineers