Synthesis of 2,3-Anthracenedicarboxylic-acid-derived Fluorophore and Chemiluminophore Incorporating Dipicolylaminomethyl Receptors, and Their Luminescence Responses to Metal Ions

Abstract

2,3-Anthracenedicarboxylic-acid-derived carboximide 1 and cyclichydrazide 2, incorporating dipicolylaminomethyl receptors, have been respectively prepared as novel fluorescence and chemiluminescence probes for metal cations.Carboximide 1 was essentially non-fluorescent in acetonitrile whereas it produced intense fluorescence (λFL max 470 nm) upon addition of Zn 2+ (off-on response).Cyclic-hydrazide 2 gave off blue chemiluminescence emission (λCL max 465 nm) after addition of alkaline H2O2 and iodide ion in dimethyl sulfoxide. Addition of metal cations, e.g. Zn 2+ , into the chemiluminescence system resulted in significant quenching of the chemiluminescence (on-off response). Therefore, the effects of the metal cation on the chemiluminescence behavior of cyclic-hydrazide 2 showed clear contrast to those on the fluorescence behavior of carboximide 1.