The designed synthesis of a series of copper(II) specific fluorogenic hydrophobic task-specific ionic liquids (TSILs) from a new naphthalene-based tetradentate ligand is reported. Absorption and fluorescence spectral studies reveal both the ligand and its derivative TSILs show exclusive selectivity towards copper(II) ions. The Stern-Volmer method for calculation of the detection limit for ligand and TSIL1-3 shows values of 0.12, 20, 17, and 15 μM, respectively. Extraction and striping studies by doping these TSILs in [bmim][NTf2] demonstrated that these TSILs are recyclable extractants for the selective recovery of Cu(II) ions from a mixture of 14 relevant metal chloride aqueous solutions in biphasic liquid-liquid extraction with approximately 95% recovery.