Synthesis And Properties Research Of Anthracene Carboxyimide-based Ratiometric Fluorescent Probes For CO And Hydrazine

Compared with traditional analytical methods,fluorescent probes with fluorescence detection and fluorescence imaging are a great powerful approach for monitoring the biomolecules in living systems,and fluorescent probes have unique advantages,such as its high selectivity,high sensitivity,noninvasive monitoring capability and usability in live organisms and so on.Many fluorescent probes functioning via single fluorescence emission signal,and the fluorescene signals(turn-on or turn-off)are widely used in detecting many important biomolecules.However,these fluorescent probes with singe signal are easily interfered by some factors such as fluorescent probe concentration,excitation intensity or emission collection efficiency.In contrast,ratiometric fluorescent probes have two fluorescence emission signals,which can effectively mitigate the above mentioned factors based the ratio of the two fluorescene signals' intensity.In the general case,ratiometric fluorescent probes need two fluorophores,which leads longer synthetic route.Meanwhile,the ratiometric probes with a single fluorophore have the shorter synthetic route,and these ratiometric probes are convenient to functionalization.Therefore,the ratiometric probes with single fluorophore is a very meaningful work.1.We synthesized an anthracene carboxyimide-based ratiometric probe for detecting CO with the reactive site allyl chloroformate.Based on the Tsuji-Trost reaction,the probe exhibited a ratio change to CO.The CO can be detected quickly(5 min),and the fluorescence intensity ratio is enhanced by about 42 times,which indicates that the probe is very sensitive to CO.In addition,Probe 1 exhibits a trend of enhanced fluorescence signal at long wavelengths(600 nm).This shows that the use of Probe 1 in biological aspects is very beneficial.Biological applications indicate that Probe 1 has low biotoxicity and also enables detection of exogenous and endogenous CO in HeLa cells.The results shows the potential of Probe 1 for biological applications.2.We used 2-fluoro-5 nitrobenzoate as a recognition site to synthesize a fluorescent probe for detecting hydrazine.Considering the two amino groups possessed by hydrazine and the ability to carry out successive nucleophilic reactions,the protecting group provides two nucleophilic sites(F atom and C=O)that react with hydrazine.Thus the protecting group can selectively respond to hydrazine.The experimental results also show that Probe 2 has good selectivity and sensitivity to hydrazine.Paper experiments show that we have developed a colorimetric tool to detect hydrazine.Moreover,cell experiments indicates that Probe 2 has low biotoxicity and can image hydrazine in HeLa cells.