Abstract
A new versatile emissive molecular probe ( 3) derived from 1,5-bis(2-aminophenoxy)-3-oxopenthane bearing two units of 6-nitro-4-oxo-4 H-chromene- has been prepared by a Schiff-base condensation method using conventional and green, ultrasound-aided, methods. The dry yellow powder was characterized as the imine species ( 3). These imine species, however, where found to rapidly convert to their enamine form ( 4) in solution, under the presence of water traces. This reaction was computationally studied through Density Functional Theory (DFT) in order to investigate the relative stability of the molecular pair 3/ 4. The sensing properties of the enamine ( 4) towards various metal ions were investigated via absorption and fluorometric titrations in solution in dichloromethane, acetonitrile and DMSO. The compound shows a fluorescent turn-off response in the presence of Cu 2+, Zn 2+, Cd 2+, Hg 2+ and Ag + over the other metal ions studied, such as Li +, Na +, K +, Ca 2+, Co 2+ and Ni 2+, being stronger for Cu 2+ and Hg 2+. The gas phase chemosensing abilities of ( 3) were also explored suggesting ( 3) as new active MALDI-TOF-MS matrix by two dry methods showing a strong selectivity towards Cu 2+ and Ag +. Our preliminary results show promising uses of ( 3) supported in PPMA films as metal ion solid chemosensor.
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