文摘
Developing simple probes to sense Al3+in vivo and in vitro in real time is highly desirable as Al3+ imbalance has been linked to a variety of diseases in human being. Here, we introduce a new, highly selective and sensitive Schiff base chemosensor, boldFont">H2bpet, based on benzophenone that can detect Al3+ in a 0.01% ethanol in 50 mM HEPES buffer medium by fluorimetric sensing. The structure of the probe, boldFont">H2bpet involves existence of keto−–enol tautomerism. Single crystal X-ray diffraction study reveals prevalence of keto form of boldFont">H2bpet in the solid state. The binding properties of boldFont">H2bpet with Al3+ was thoroughly investigated by fluorescence spectroscopy and ESI–MS analyses. The binding of Al3+ to the probe boldFont">H2bpet, induces distinct 1H and 13C NMR shifts in favour of boldFont">H2bpet (keto form):Al3+ aggregate. The sensing mechanism of boldFont">H2bpet toward Al3+ and composition of boldFont">H2bpet:Al3+ aggregate was proposed and established by DFT/TDDFT calculations. Its application in fluorescent imaging in HepG2 cells was also tested. This report demonstrates an advancement in detection of Al3+ with the introduction of a new benzophenone containing Schiff base chemosensor.