New coumarin-urea based receptor for anions: a selective off–on fluorescence response to fluoride
2012; Elsevier BV; Volume: 68; Issue: 19 Linguagem: Inglês
10.1016/j.tet.2012.02.067
ISSN1464-5416
AutoresGianluca Ambrosi, Mauro Formica, Vieri Fusi, Luca Giorgi, Eleonora Macedi, Giovanni Piersanti, Michele Retini, Maria Antonietta Varrese, Giovanni Zappia,
Tópico(s)Analytical Chemistry and Sensors
ResumoA 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 1H NMR, UV–vis, and fluorescence titration. It was found that L forms stable [LG] and [LG2] 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.
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