New coumarin-urea based receptor for anions: a selective off-on fluorescence response to fluoride

作者：Ambrosi Gianluca; Formica Mauro; Fusi Vieri^*; Giorgi Luca; Macedi Eleonora; Piersanti Giovanni; Retini Michele; Varrese Maria Antonietta; Zappia Giovanni

来源：Tetrahedron, 2012, 68(19): 3768-3775.

DOI：10.1016/j.tet.2012.02.067

• Coumarin
• Fluoride
• Fluorescence
• Urea
• Anion coordination

A novel fluorosensor for anions, 1,11-bis(4-methylcoumarin-7-yl)-6-methyl-1,3,6,9,11-pentaazaundeca-2,10-dione (L), which contains two coumarin-urea units spaced by a flexible diethylenetriamine fragment, was easily prepared in 65% yield by a one-pot two-step procedure. The binding ability of L toward several anions (G) was evaluated by H-1 NMR, UV-vis, and fluorescence titration. It was found that L forms stable [LG] and [LG(2)] species in both DMSO and CH3CN solvents. Furthermore, the fluorescence emission of L in the visible range (400 nm) is affected by the presence of anions; it is quenched by acetate, chloride, and pyrophosphate while it is enhanced by fluoride. Thus, this novel fluorosensor provides a selective off-on response to the presence of fluoride in solution.

• 出版日期2012-5-13