Quinoline based reversible fluorescent probe for Pb~(2+); applications in milk,bioimaging and INHIBIT molecular logic gate

摘要

We report the modular design and synthesis of an amine dangled Schiff base quinoline-morpholine conjugate (QMC) for highly selective detection of Pb2+ ions via fluorimetry. The sensing strategy of QMC towards Pb2+ ion exhibits a large blue shift with fluorescent enhancement via the intramolecular charge transfer (ICT) process. At the same time, QMC coordination with Pb2+, the C-N single bond rotation between quinoline and morpholine rings and the C=N isomerization process were blocked. Best of our knowledge, this is the first blue shifted turn on fluorescent chemosensor for Pb2+ ion via the ICT process. Furthermore, QMC selectively detects Pb2+ ion without any interference with alkali, alkaline earth, and transition metal ions, and limit of detection (LOD) downs to 13 mu M, which is a permissible level of Pb2+ ion in drinking water reported by WHO. The 1:2 binding stoichiometry between QMC and Pb2+ was confirmed by fluorimetric, H-1 NMR titration, mass spectrometry, and theoretical studies. Finally, QMC was potentially applied for the sensing of Pb2+ ions in milk, red wine, live cells and an INHIBIT molecular logic function was constructed by using Pb2+ and EDTA as chemical inputs.