Study On Design,Synthesis Of Novel Quinoline Fluorescent Probes And Their Properties

Due to seriously pollution of metal ions to soil,water and life systems,this threat the health of human who are at the top of the food chain.Therefore,we need to develop a new way which is simple,fast and on-line to detection of the metal ions concentration of soil,water and biological samples.Although a variety of detection instruments have been used,but they were certain limitations in practical applications,because of the high cost of purchase and maintenance of these instruments and complex pre-processing of the samples.In recent years,fluorescent probes have been applied in biological,environmental monitoring and other fields,due to they were cheap and easy to synthesis.More importantly,fluorescent probes required a bit of samples in application and had high selectivity and sensitivity,they were usually convenience of operation and small harm to biological samples.Quinoline and its derivatives as good chelating agents of metal and they have perfect fluorescence properties.However,due to the poor selectivity to metal and the excitation and emission wavelengths in shorter wavelength range,their applications were not extensive.Therefore,it is necessary to chemically modify the quinoline and its derivatives,expect that the new probe can achieve the purpose of identification to metal ions in high selectivity and sensitivity.And study the value of potential applications at actual and biological sample of them with fluorescence imaging techniques.In this paper,several novel probes which with quinoline as fluorophore were designed and synthesized and their structures were characterized.The abilities that new probes selective complexation and fluorescence sensing to metal ions were evaluated by UV-vis,fluorescence spectroscopy,ESI-MS,1H NMR and fluorescence imaging.Some metal complexes as new probes were used to identify H₂PO₄^-and HPO₄^2-in the aqueous solutions.This paper consists of four chapters,the general content are as follows:（1）The mechanism of probe sensing and the progress of quinoline fluorescence probe were introduced,and the design conception of this paper was put forward.（2）Two probes 2a and 2b with 8-Hydroxyquinaldine as fluorophore were designed and synthesized,and their performance of sensing were studied by fluorescence emission.2a was found to present high selectivity and sensitivity fluorescence sensing ability for Al³⁺ in aqueous solution and living cells.2b could act as selective fluorescent quenching probe for Cu2+ with formation of 1:1 complex and at the same time 2b-Cu2+ complex could be a new selective fluorescent enhanced probe for H₂PO₄^-and HPO₄^2-in Me OH-H₂O solution and living cells.（3）The probes 3a,3b and 3c with 8-Hydroxyquinaldine derivatives as fluorophore were designed and synthesized,and the properties of fluorescence sensing were studied.3a could fluorescent sensing for Al³⁺ and Fe³⁺ with high selectivity and sensitivity in solution and living cells and the colorific and fluorescence change of solution were different observed.Fluorescence titration,Job curve and 1H NMR indicated that 3a with Al³⁺ or Fe³⁺ formed 1:2 complex.（4）Two probes 4a and 4b with 2-（Hydroxymethyl）quinolin-8-ol as fluorophore were designed and synthesized and their performance to selectively identify metal ions were studied in aqueous solution.Fluorescence spectroscopy,UV-vis,1H NMR,ESI-MS and X-ray crystallography showed that probe 4a for Cd2+ had good recognition and 1:1 complex formed between 4a and Cd2+.Finally,the fluorescence performance of 4a on Cd2+ was studied by fluorescence imaging that indicated 4a had potential application value in the organism.