Synthesis And Application Of Acylhydrazone Fluorescent Probes With AIE Characteristic

In recent years,aggregation induced enhancement?AIE?molecules have a very broad application prospect in the fields of new luminescent materials and biosensors due to their strong fluorescence at high concentration.At the same time,it can recognize anion and anion and realize the versatility of chemical sensor.For this purpose,we designed and synthesized five kinds of acylhydrazone compounds,which not only have good aggregation induced enhancement property but also have good recognition ability for Al³⁺,PPi,Ba²⁺and CO₃^2-,and have been applied to the environment and biology.Therefore,some significant experimental results are obtained as follows:1.A simple and efficient fluorescent probe L1 was synthesized by using2-hydroxy-1-napHthaldehyde and iso-phthalic dihydrazide.By adjusting the content of water in solvent and detecting the change of fluorescence signal,it is proved that L1 has good property of concentrated fluorescence.And the sensor displays a highly selective recognition and a lower detection limit(5.924×10^-6M)for Al³⁺over other tested metal ions,which has a significant fluorescence enhancement in the mixed ETOH and water?1:1?.This probe L1 has a binding ratio of 1:2.In addition,the L1-2Al³⁺showed highly selective sequential recognition of PPi with good sensitivity.The detection limit of L1-2Al³⁺to PPi could reach 4.756×10^-55 M,which illustrated L1-2Al³⁺had the potential application value.2.Fluorescent probes L2 and L3 were synthesized based on2-hydroxy-1-naphthalene formaldehyde,2,6-pyridine diformyl hydrazide and thiophene diformyl hydrazide.By adjusting the content of water in solvent and detecting the change of fluorescence signal,it is proved that L2/L3 has good property of concentrated fluorescence.And the sensors displays a highly selective recognition for Al³⁺over other tested metal ions,which has a significant fluorescence enhancement in the mixed DMF and water?1:1?.A lower detection limit of Al³⁺was measured based on 10?M receptor titration experiment,which indicates that the probe L2/L3 has the higher sensitive recognition for Al³⁺.When the molar ratio of probe L close to 0.66,the fluorescence emission intensity shows a turning point,which indicates that the combination ratio of probe L2/L3 with Al³⁺is 1:2.3.A simple fluorescent probe L based on pyridoxal and picolinylhydrazide was designed and synthesized.By adjusting the content of water in solvent and detecting the change of fluorescence signal,it is proved that L4 has good property of concentrated fluorescence.Probe L4 showed high selectivity to Ba²⁺on various cations and has a lower detection limit(6.351×10^-6M)at EtOH/H₂O?1/1,v/v,pH=7.4?.This probe L has a binding ratio of 2:1.The potential application of probe L4 was evaluated and the results showed that can detect actual water and food salt,the recoveries are in the range of 96–100%and75–101%.4.The ratio fluorescent probe L5 was designed and synthesized based on 2,6-diformyl-4-methylphenol and N-?naphthalene-1-group?methionyl hydrazide.By regulating the content of water in the solvent and detecting the change of fluorescence signal,it is proved that L5 has good property of concentrated fluorescence.Under the ethanol-water?8:2?system,CO₃^2-can be identified with high selectivity,and the detection limit can reach 3.938×10^-6m,with strong anti-interference performance.The binding constant is 1.762×10¹⁰.Through the real water and cell imaging experiments,probe L5 can detect CO₃^2-in real water and living cells.