Synthesis Of Polycyclic Phenazine Host Compounds And Their Recognition Properties For Object

Organic fluorescence chemistry sensor is more and more important because it has the advantages of easy synthesis,short response time,good ion selectivity and high detection limit.In the environmental sciences,biological sciences and other fields have a broad application prospects.Phenazine compounds,due to their good electrochemical properties and easy to be functionalized,the application of ion recognition is of concern.Chapter one:This chapter mainly introduces the synthesis and application of phenazine and its derivatives,and the application of phenazine compounds in the recognition of host and guest.According to the different identifying objects in the supramolecular chemistry,the identification can be divided into the following three types:?1?the recognition of the anion by the phenazine derivative;?2?the recognition of the cation by the phenazine derivative;?3?Identification of Small Molecules by phenazine derivatives.Chapter two:In this chapter,a fluorescent sensor molecule Y1 was synthesized by the method of literature.The UV spectroscopy and the pH stability of Y1 to anions and cations were systematically studied.The results show that the addition of Fe³⁺and Cu²⁺can cause the fluorescence of the solution to be quenched when 12 different kinds of cations are added to the host solution.After adding 10 different kinds of anions to the host solution,F^?,I^?,AcO^?and CN^?all make Y1 change in the ultraviolet spectrum,while Y1 on the fluorescence spectrum shows selective identification of CN^?,but the effect poorly.The experimental results show that the sensor molecule Y1 is not very stable to pH.On the basis of these experimental results,we believe that the sensor molecule Y1 has been unable to meet the developmental needs of today's fluorescent probe,this property has been unable to meet the specific identification of the test object and the stability of pH.Therefore,it is very important to design and synthesize new type of phenazine fluorescent probe.Chapter three:An imidazo-phenazine lactam compound S1 was designed and synthesized.The structures of the composites were characterized by ¹H NMR spectroscopy,¹³C NMR spectroscopy and high resolution mass spectrometry.The synthesis conditions of S1 were discussed and optimized.When various anions?F^?,Cl^?,Br^?,I^?,AcO^?,H₂PO₄^?,HSO₄^?,ClO₄^?,CN^?and SCN^??were added to the DMSO solution of S1,it was found that only CN^?so that the fluorescence spectrum of S1 showed a significant decline and redshift occurred.The fluorescence color of the solution changed from yellow to orange,indicating that S1 has a good selectivity for CN^?.The results of anti-interference experiments show that this recognition process is not affected by other anions.The minimum detection limit of fluorescence spectrum of S1 to CN^?is 9.96×10^?7 mol/L,which is lower than that of drinking water in the world.Mechanism studies have shown that S1 is a reactive type recognition CN^?fluorescence sensor.In addition,we mixed S1 into solid-state silica gel to prepare solid CN^?recognition materials and successfully used to identify solid NaCN and to detect CN^?aqueous solutions.Chapter four:12 cations(Fe³⁺,Hg²⁺,Ca²⁺,Cu²⁺,Co²⁺,Ni²⁺,Pb²⁺,Zn²⁺,Cr³⁺and Mg²⁺)were added to the DMSO solution of S1.It was found that only the addition of Fe³⁺caused the fluorescence spectrum of S1 to the fluoresce-off-phenomenon.Indicating that S1 has a good selectivity for Fe³⁺.The results of anti-interference experiments show that this recognition process is not affected by other cations.Continuous identification experiments show that S1 loading Fe³⁺can continuously identify CN^?and SCN^?.The mechanism studies show that S1 is a reactive ligand for the identification of Fe³⁺fluorescence sensors.In addition,we mixed S1 on solid silica gel to prepare solid Fe³⁺identification material and successfully used to identify solid Fe?ClO₄?₃,and then continuously identify solid NaCN and NaSCN.Chapter five:20 kinds of amino acids?L-phenylalanine,L-glutamine,L-isoleucine,L-threonine,L-glutamic acid,?-alanine,L Serine,L-methionine,L-valine,L-tyrosine,L-arginine,DL-aspartic acid,L-proline,L-histidine,L-leucine,Glycine,L-tryptophan,L-lysine,L-asparagine and L-cysteine?were added to the DMSO solution of S1.It was found that only the addition of L-lysine caused red shift of the fluorescence spectrum of S1.Under the UV-analyzer,we observed that the fluorescence color of the solution changed when L-lysine was added to the solution of S1,indicating that S1 has a good selectivity for L-lysine.The stability test of pH results show that the identification process of pH change is relatively stable.The mechanism studies show that S1 is a reactive type recognizing L-lysine fluorescence sensor.Finally we make a conclusion to the article and look forward to the development of phenazine derivatives in the field of ion recognition.Some spectra are listed.