Abstract
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, H2bpet, based on benzophenone that can detect Al3+ in a 0.01% ethanol in 50mM HEPES buffer medium by fluorimetric sensing. The structure of the probe, H2bpet involves existence of keto−–enol tautomerism. Single crystal X-ray diffraction study reveals prevalence of keto form of H2bpet in the solid state. The binding properties of H2bpet with Al3+ was thoroughly investigated by fluorescence spectroscopy and ESI–MS analyses. The binding of Al3+ to the probe H2bpet, induces distinct 1H and 13C NMR shifts in favour of H2bpet (keto form):Al3+ aggregate. The sensing mechanism of H2bpet toward Al3+ and composition of 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.
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