Ellagic acid (EA), a natural polyphenol, features a highly organized planar structure with an extensive sp2 carbon-conjugated area, making it favorable for light energy absorption and fluorescent emission. However, this planar structure can easily aggregate through π-π stacking, leading to aggregation-caused quenching of fluorescence. In this research, aniline-doped ellagic acid (EAAn2) was successfully synthesized via a C-N coupling reaction to address this issue. The fluorescence properties of EAAn2 in various organic solvents were thoroughly investigated. Compared to EA, EAAn2 exhibited a red shift in fluorescence emission, primarily revealing yellow fluorescence instead of the green fluorescence of EA. Moreover, the fluorescence intensity and the concentration at which aggregation-caused quenching occurs for EAAn2 were substantially improved due to the two grafted aniline molecules.EAAn2 was utilized as a molecular fluorescent probe in DMSO to detect three kinds of metal ions: alkali and alkaline-earth metal ions, transition metal ions, and post-transition metal ions, using EA as a control. It was found that the combination of EAAn2 with these metal ions exhibited stronger fluorescence intensity than EA and effectively resisted the blue shift in fluorescence emission due to aniline doping. Based on these results, Mg2⁺ ions could be clearly distinguished from other alkali and alkaline-earth metal ions by differences in their fluorescence emission, as could Cr2⁺ ions among transition metals. This research effectively enhances the fluorescence properties of EA through C-N coupling and demonstrates its greater potential in the detection of metal ions, providing fundamental and valuable information for future fluorescent applications.
Read full abstract