Phthalide derivatives incorporating mono- and di-picolylamino functionalities at the 6-position have been prepared as novel fluoroionophores and their fluorescence responses to metal cations have been investigated. These phthalides not only exhibited efficient fluorescence in an aqueous medium but also displayed fluorescence on-off response upon addition of transition-metal cations, namely Cu(2+). The 6-aminophthalide fluorophore served as the core of the fluorescent probes although it has rarely been applied to a chemosensor. To the best of our knowledge, these modified phthalides are the first 6-aminophthalide-derived fluorometric probes for metal cations, namely Cu(2+).

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.