Design, Synthesis And Sensing Of Pyrene Derivative Fluorescent Probes

How to obtain high-quality chemical and biological quantitative information with simplicity and accuracy is one of the central task of analytical science. Fluorescent probes have been widely used to facilitate the detection of chemical, biological, medical and material analytes due to the high sensitivity and good selectivity. Pyrene and its derivatives have been widely used in fluorescent sensing and molecular markers owing to high quantum yield, long fluorescence lifetime and chemical stability. Based on the Schiff base reaction under mild reaction conditions, we designed and synthesized a series of novel pyrene derivative fluorescent probes for the highly sensitive detection of intracellular Zn2+, thiophene and ClO-. Good effects have been achieved and the main jobs are as follows:(1) The study of pyrene derivatives fluorescent probe(L1) for Zn2+Using 1-pyrenecarboxaldehyde and anthranilic acid, a new ultrasensitive chemical sensor 2-(pyren-1-ylmethylene amino) benzoic acid(L1) was synthesized and exhibited good selectivity for Zn2+ ion detection. The pyrene-containing schiff base probe showed strong fluorescence in protic solvent such as methanol and ethanol, whereas it showed almost no fluorescence in aprotic solvent such as DMSO, THF and CH3 CN. Additionally, L1 probe can be used for the ultrasensitive detection of cellular Zn2+. Hela cell showed almost no fluorescence in the L1-PBS system. After the addition of 5 nmol/L Zn2+, bright fluorescence can be observed with a fluorescent microscope due to the interaction between L1 and cellular Zn2+.(2) Pyrene derivative fluorescent probe(L2)-AgNPs for the quantitative detection of thiopheneNano-sized silver particles have special physical and chemical properties. They have been widely used in the areas of sensor and pharmaceutical analysis. In this chapter, the synthesized probe 4-(pyren-1-ylmethylene amino) benzoic acid can combined with nano silver specificity in ethanol/acetonitrile aqueous solution. With the increases of the concentration of silver nanoparticles, the fluorescence enhanced linearly, which is obvious with low detection limit and high sensitivity. After the addition of thiophene, the specific S-Ag bonds may be formed via silver nanoparticles and S atoms of thiophene, leading to the decreaseds action between the schiff base and AgNPs. Hence the fluorescence was lowered. Based on this phenomenon, the thiophene content in gasoline, simulating gasoline and oil was further tested and the recovery is between 66.4% and 113%, which proved the feasiblility of the above method. The limit of detection is as low as 0.25 nmol/L.(3) Pyrene derivatives fluorescent probes(L3) for the detection of ClO-Using 1-pyrenecarboxaldehyde and 3-amino-2-naphthoic acid, a new fluorescence probe(L3) was synthesized and characterized by NMR, IR and UV-vis spectrum. For the probe, the suitable conditions such as temperature, concentration and pH was investigated. The fluorescence and ultraviolet spectra of L3 were studied in various solvents. The synthesized pyrene-containing schiff base fluorescence probe could rotate freely and no fluorescence was presented. When adding anionic ClO-, N atoms in the C=N were removed, leading the enhancement of the fluorescence. A good linear relationship in the range of 2×10-12 mol/L ~ 4×10-6 mol/L is obtained for ClOdetection(S/N=3).