Studies On The Synthesis And Properties Of Novel Hydrazone Compounds

In recent years,the excessive content of anions and cations,such as fluoride ions and zinc ions,have been an important cause of water pollution and food pollution.The rapid and accurate recognition of these ions is of vital importance for environmental protection.In the field of supramolecular chemistry,using weak interaction between molecules and ions to achieve ion recognition is an important research direction.Among various types of ion-sensing compounds,hydrazone compounds have attracted widespread attention due to their abundant ion-complexation sites and flexible ion-coordination forms.In this paper,several series of new ion-sensing hydrazone compounds were synthesized,which achieved the efficient recognition of different ions in the state of solution or gel.The main content of this article is divided into the following four parts:Firstly,a series of pyridyl acylhydrazone derivatives were synthesized,and their gelation properties were studied by CGC test.Microscopic characteristics of the gels were studied by SEM and XRD,and the driving forces of gelation were studied by concentration-variable¹H NMR.The anion response experiment showed that B–3can both semi-quantitatively recognize F^-in THF and qualitatively recognize F^-and AcO^-in the acetonitrile gel.The cation response experiment showed that B–3 can qualitatively recognize Zn²⁺and Cu²⁺in the acetonitrile gel.Secondly,a series of quinolinyl hydrazone derivatives were synthesized,and their gelation properties were studied by CGC,SEM,XRD and concentration-variable¹H NMR.The anion response experiment showed that the THF solution of Q–1 can achieve the"naked eye"recognition F^-,AcO^-and H₂PO₄^-colorimetrically.The THF solution of Q–3 can recognize F^-both selectively and competitively.Then,the tetraphenylethylene hydrazone compound TPE–C₁₂was synthesized and its fluorescence characteristics in the DMSO/H₂O system were studied by FR.The results showed that TPE–C₁₂has a significant AIEE effect and a large Stokes shift.The anion response experiment showed that the THF solution of TPE–C₁₂can recognize F^-both selectively and competitively.In DMSO/H₂O solution,TPE–C₁₂can quantitatively recognize of F^-within the range of 0–0.6 eq according to the change of fluorescence intensity.Finally,a series of triphenylamine trihydrazone compounds containing PEG side chains were synthesized and their anion response abilities were studied.The results showed that TPA–2 and TPA–3 can recognize F^-,AcO^-and H₂PO₄^-at the same time in THF solution.However,UV-Vis research showed that TPA–2 recognizes F^-slightly better than TPA–3,while TPA–3 recognizes AcO^-slightly better than TPA–2,indicating that the length of PEG side chain（degree of polymerization）has a significant effect on the anion recognition ability of such compounds.