Ratiometric Fluorescent Sensor for Copper(II) and Phosphate Ions from Aminopyrene Derivatives

Three derivatives of 1-aminopyrene are functionalized with 2-picolyl and 2-picolinyl groups and tested as fluorescent sensors for metal ions. The target compounds are successfully synthesized in 50 to 90% yields and characterized by 1H-NMR, 13C-NMR, and HRMS. The compound with an amino picolyl group (P1) exhibits an excellent selectivity towards Cu(II) ion as the fluorescent signal shifts from 433 to 630 nm. From a fluorescence titration experiment, the limit of detection for Cu(II) ion is estimated to 0.19 µM. That the fluorescence spectral shift by Cu(II) ion is reliant on the use of acetonitrile as a co-solvent and the results from cyclic voltammetry and UV-Vis spectroscopy suggest that the sensing mechanism involves a coordination complex between the P1, acetonitrile, and Cu(II) ion. Furthermore, this P1-Cu complex can also be used as a selective fluorescent sensor for PO43- ion with a detection limit of 0.44 µM.

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