Novel coumarin fluorescent dyes: Synthesis, structural characterization and recognition behavior towards Cu(II) and Ni(II)

• Published in: Dyes and pigments Vol. 91; no. 3; pp. 309 - 316
• Main Authors: Li, Hongqi, Cai, Li, Li, Jinxing, Hu, Yixin, Zhou, Pingping, Zhang, Jiming
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 01.12.2011
• Subjects: Blue shift; Character recognition; Coumarin; Cu(II) ion; Dye; Dyes; Fluorescence; Fluorescent; Fluorescent dyes; Ni(II) ion; Nuclear magnetic resonance; Recognition; Fluorescent; Dye; Cu(II) ion; Coumarin; Recognition; Ni(II) ion
• ISSN: 0143-7208; 1873-3743
• DOI: 10.1016/j.dyepig.2011.05.011

A series of novel coumarin dyes ( 3–12) were designed and synthesized. The structures of the dyes were characterized by IR, 1H NMR, 13C NMR, 19F NMR, MS and single crystal X-ray diffraction. 3-(2-Benzoylhydrazonotrifluoroethyl)-7-( N, N-diethylamino)coumarin ( 11) could recognize Cu 2+ and Ni 2+ selectively in aqueous solution. Upon addition of Cu 2+ or Ni 2+ to 11 a blue shift or a bathochromatic shift of the absorption band was observed while the emission band blue-shifted with decrease in the fluorescence intensity. Upon addition of Cu 2+ the color of the solution of 11 changed from orange to red. The results showed that 11 could be used as an optical chemosensor of Cu 2+ and Ni 2+. ► Novel coumarin dyes were synthesized and characterized. ► A coumarin dye ( 11) could recognize Cu 2+ and Ni 2+ selectively in aqueous solution. ► Upon addition of Cu 2+ the color of the coumarin solution changed from orange to red.