Fluorescent chemosensors based on 4-hydroxy cyclopentenones were synthesized by the base catalyzed reaction of 1,5-diphenyl-pentane-1,3,5-trione with benzil and thenil. The molecule obtained by the benzil reaction was found to be useful for the selective detection of Fe 3+ by fluorescence turn-off, while the molecule synthesized by the thenil reaction was useful for selective detection of Cu 2+ by fluorescent turn-on. Details of the synthesis, complexation mode, nature of binding, reversibility, and pH studies of the two sensors are discussed. The studies revealed that the sensors were suitable for determining Fe 3+ and Cu 2+ content in real water samples.
A mild, efficient and simple method for the synthesis of 3,6-dihydroxy-1,2,4,5-tetracarboxylic tetraalkyl esters using cerium(IV) ammonium nitrate mediated oxidation of 1,3-acetone dicarboxylates has been developed. The detailed absorption and emission studies of the synthesized compounds reveal that these molecules have appreciable quantum yields and possess large Stokes shift values.
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