Synthesis of a novel fluorescent Schiff base as a possible Cu(II) ion selective sensor.

In this study a new fluorescent Schiff base; 1,1'-(4,4'-oxybis(4,1-phenylene)bis(azan-1-yl-1-ylidene))bis(methan-1-yl-1-ylidene)dinaphthalen-2-ol (2-HNA) was synthesized and characterized by FT-IR, UV-vis, and (1)H and (13)C-NMR techniques. Photoluminescent properties of 2-HNA were investigated in different solvents including methanol, THF, DMF, DMSO, acetone, acetonitrile, and dichloromethane. 2-HNA was found to have higher emission intensity and Stoke's shift value (lambda(ST)) in methanol solution. Relative emission intensity changes (I(0)-I/I(0)) of 2-HNA in methanol/water mixtures depending on different Cu(+2) ion concentrations were determined and a linearized plot was obtained. Possible interference of some other transition metal ions was also determined. Sensitivity limit of the new sensor was found to be higher than 5 x 10(-7) mol/L. 2-HNA has quite high selectivity against Cu(+2) ion and, thus, can be used as a new fluorescence Cu(+2) ion sensor in practice.