ABSTRACT
A novel Schiff base chemosensor HMID, ((E)1((2hydroxy3methoxybenzylidene)amino)imidazolidine2,4dione), have been designed and synthesized. Sensor HMID showed a selectivity to Zn2+ through fluorescence enhancement in aqueous solution. Its detection limit was analyzed as 11.9⯵M. Importantly, compound HMID could be applied to image Zn2+ in live cells. Detection mechanism of Zn2+ by HMID was suggested to be an effect of chelation-enhanced fluorescence (CHEF) by DFT calculations. Moreover, HMID could detect Cu2+ with a change of color from colorless to pink. The selective detection mechanism of Cu2+ by HMID was demonstrated to be the promotion of intramolecular charge transfer band by DFT calculations. Additionally, HMID could be employed as a naked-eye colorimetric kit for Cu2+. Therefore, HMID has the ability as a 'single sensor for dual targets'.
Subject(s)
Colorimetry/methods , Copper/analysis , Fluorescent Dyes/chemistry , Molecular Imaging/methods , Zinc/analysis , Chelating Agents/chemistry , Color , Density Functional Theory , Fluorescent Dyes/chemical synthesis , Fluorescent Dyes/metabolism , HeLa Cells , Humans , Limit of Detection , Magnetic Resonance Spectroscopy , Molecular Structure , Schiff Bases/chemistry , Spectrometry, Mass, Electrospray Ionization , Spectrophotometry, UltravioletABSTRACT
A new bi-functional chemosensor 1 based on 3,5-dichlorosalicylaldehyde and 2-(methylthio)aniline has been synthesized. It can detect Cu2+ with a color change from pale yellow to dark yellow in aqueous solution. The selective mechanism of 1 for Cu2+ was proposed to be the enhancement of the intramolecular charge transfer (ICT) band, which was explained by theoretical calculations. The sensor 1 could be used to detect and quantify Cu2+ in water samples. In addition, the sensor 1 displayed "turn-on" fluorescence response only to Zn2+, based on an effect of chelation-enhanced fluorescence (CHEF). Therefore, 1 can serve as a 'single sensor for two different targets' with dual modes.
