A 1,8-Naphthalimide-based Tripodal Fluorescent Chemosensor to Selectively Detect Copper Ions

Abstract

A 1,8-naphthalimide-based tripodal fluorescent ligand (L3) was synthesized through the copper (I) catalyzed Huisgen azide-alkyne cycloaddition reaction of 2-(2-azidoethyl)-6-morpholino-1 H-benzo[de]isoquinoline-1,3(2 H)-dione with triproparagylamine. Naphthalimide acts as the fluorophore while the triazole and amine nitrogens chelate the metal ion. L3 showed a selective fluorescence turn-off for Cu(II) over other metal ions in aqueous acetonitrile solution. A Job’s plot, Benesi-Hildbrand plot and high-resolution mass spectrometry data confirm a 1:1 binding stoichiometry with a binding constant of 7.8 х10⁵ M^− 1 while addition of disodium EDTA demonstrates its reversibility. The structure and stability of the complex was supported by theoretical calculations. The limit of detection for Cu(II) was calculated to be 0.3 µM which is considerably lower than WHO recommended Cu(II) limit in drinking water.