Synthesis and application of purine-based fluorescence probe for continuous recognition of Cu2+ and glyphosate

In this study, a novel fluorescent sensor, N,N-dimethyl-4-((2-(8-m-ethyl-9-(naphthalen-1-yl)-9H-purin-6-yl)hydrazineylidene)methyl)aniline(PHA), which was constructed via Schiff base reaction of purine derivatives and dimethylaminobenzaldehyde. This probe showed significant selective fluorescence quenching of Cu2+, and accompanying with an increase in Cu2+ concentration and a change in solution color from colorless to yellow. The outstanding features of PHA include low detection limit (0.429 μM), strong anti-interference ability and fast response time. We further investigated the chelation mechanism of PHA and Cu2+ by Job's plot experiment, density generalization theory (DFT), and the probe PHA can form a 1:2 complex with Cu2+ ions, leading to a fluorescence quenching process, thus realizing the rapid detection of Cu2+. In addition, this new fluorescent sensor [PHA-Cu2+] can be used to detect pesticide residues in solution. When the [PHA-Cu2+] system was mixed with glyphosate solution, that a fluorescence recovering was observed. This may be because glyphosate chelates more strongly with Cu2+ ions, making the copper ions dissociated from the [PHA-Cu2+] system. The detection limit of the fluorescent sensor [PHA-Cu2+] for glyphosate was 18.77 nM. Finally, the sensor system has been successfully applied in fluorescence imaging of glyphosate in living cells.