A new 1,8-naphthalimide-based fluorescent “turn-off” sensor for detecting Cu²⁺ and sensing mechanisms

Abstract

In this article, a new “turn-off” fluorescent sensor N- n-butyl-4-{2-[(ethylimino)methyl]phenol}-1,8-naphthalimide (HL) for CuII ions is synthesized, which contains a 1,8-naphthalimide moiety as the fluorophore and a Schiff base as the recognition group. As expected, it exhibits high selectivity and sensitivity for detecting CuII ions over other common metal ions in acetonitrile–2-(4-(2-hydroxyethyl)-1-piperazinyl)-ethanesulfonic acid (HEPES) (1:1 v/v, pH = 7.4) solution. In addition, the fluorescence intensity for HL showed a good linearity with the concentration of CuII ions in the range of 0.5–5.0 μM. The 2:1 binding stoichiometry between HL and CuII ions was established on the basis of combined fluorescence titrations, a Job’s plot, single-crystal X-ray analysis and mass spectrometry. The quenching response of HL toward CuII ions is attributed to the reverse photoinduced electron transfer mechanism. The proposed sensor HL is preliminarily applied to quantify CuII ions in water samples from the Yellow River and tap water.