Design And Synthesis Of Novel Boronyl Pyridine Bipyrene Compounds And Their Application

Carbohydrates and nucleic acids are two main basic substances for organisms,which take part in the regulation of various physiological processes including genetic information transmission,energy supply for life activities,and cell recognition.For instance,Fructose,a kind of reduced monosaccharide with high sweetness and low glycemic index in nature,is widely used in food and medical fields.Many single nucleotides,such as adenosine triphosphate（ATP）and coenzyme（NADH）,also have a variety of important biological functions.Therefore,the selective detection and identification of some important monosaccharides and mononucleotides have become a hot point recently.Based on the reversible and covalent binding of boronic acid groups to 1,2/1,3-cis-dihydroxy compounds,a variety of boronic acid-based fluorescent probes have been developed for the detection of carbohydrates and nucleosides.In this thesis,a series of novel boronic acid-based pyridine pyrene compounds were designed,synthesized,and used for the fluorescent detection of monosaccharides and mononucleotides.The specific research content of this thesis is as follows:1.Series dual-boronic acid pyridine pyrene compounds（M-1/2/3 and P-1/2/3）were firstly successfully prepared synthesized using 1,6-dibromopyrene as the starting material through Suzuki coupling reaction and nucleophilic substitution reaction.The structure of the new compounds was determined ¹H NMR and ¹³C NMR.The basic spectral parameters of the new compounds were measured by UV-Vis absorption and fluorescence emission spectrum.All the compounds displayed large Stokes shift（>100nm）and dual-boronic acid para-pyridine pyrene compounds（P-1/2/3）showed high fluorescence quantum yield（Φ>0.20）.2.The new dual-boronic acid pyridine pyrene compounds were used as the one-component fluorescent probes for detection and identification importing single nucleotides.The spectral results showed the fluorescence of dual-boronic acid meta-pyridine pyrene compounds（M-1/2/3）was stronger after binding to the single nucleotides,whereas dual-boronic acid para-pyridine pyrene compounds（P-1/2/3）displayed an opposite change.At the same time,M-1/2/3 can be used for the qualitative and quantitative detection of NADH.3.The two-component fluorescent sensors（TCF-1/2/3/4/5/6）were prepared with dual-boronic acid-based pyridine pyrene compounds（quencher）and 8-hydroxypyrene-1,3,6-trisulfonic acid trisodium salt（fluorophore）and used for detection and identification importing monosaccharide.The spectral experimental results showed enlarging theπ-system of core structure in quencher could enhance the quenching ability of the fluorophore.All two-component fluorescent sensors were found to be high selectivity for fructose.TCF-1 was further applied to the evaluation of sucrose phosphorylase activity.