1,8-Naphthalimide derivative-based turn-off fluorescent probe for the detection of picrate in organic aqueous media

Abstract

Abstract The synthesis of a simple fluorescent naphthalimide-based receptor N-allyl-4-iminodi(N-butylacetamide)-1,8-naphthalimide 3 was carried out as a selective picrate (Pic–) anion probe, and the detecting behavior of this probe was studied by fluorescence spectroscopy. In DMF solution, the interaction of compound 3 with different anions, including Pic–, F–, Cl–, Br–, I–, OH–, Ac–, NO3 –, ClO4 –, SCN–, SO3 2–, SO4 2–, H2PO4 –, and HPO4 2–, revealed significant fluorescence quenching only with the Pic– anion. By adding the picrate anions, green-yellow fluorescence emission quenches, which is easily observed by naked eyes under a 365 nm UV light irradiation. This phenomenon is essential for producing a highly selective and sensitive fluorescent probe for picrate anions. The probe can be applied to the quantification of Pic– with a linear range covering from 4.97 × 10–6 to 6.82 × 10–5 m and a detection limit of 5.8 × 10–7 m. Most importantly, probe 3 has a high selectivity for picrate over competitive anions and picrate-containing analytes, which meet the selective requirements for practical application. Thus, the present results would be inspiring findings in the future design of reaction-based fluorescent turn-off probes for the environmentally relevant picrate probe.