A Chromo-Fluorogenic Naphthoquinolinedione-Based Probe for Dual Detection of Cu(2+) and Its Use for Various Water Samples

The presence of an abnormal amount of Cu(2+) in the human body causes various health issues. In the current study, we synthesized a new naphthoquinolinedione-based probe (probe 1) to monitor Cu(2+) in different water systems, such as tap water, lakes, and drain water. Two triazole units were introduced into the probe via a click reaction to increase the binding affinity to a metal ion. In day-light, probe 1 dissolved in a mixed solvent system (HEPES: EtOH = 1:4) showed a vivid color change from light greenish-yellow to pink in the presence of only Cu(2+) among various metal ions. In addition, the green luminescence and fluorescence emission of the probe were effectively bleached out immediately after Cu(2+) addition. The limit of detection (LOD) of the probe was 0.5 µM when a ratio-metric method was used for metal ion detection. The fluorescence titration data of the probe with Cu(2+) showed a calculated LOD of 41.5 pM. Hence, probe 1 possesses the following dual response toward Cu(2+) detection: color change and fluorescence quenching. Probe 1 was also useful for detecting Cu(2+) spiked in tap/lake water as well as the cytoplasm of live HeLa cells. The current system was investigated using ultraviolet-visible and fluorescence spectroscopy as well as density functional theory calculations (DFT).