Synthesis And Functions Study Of Several Bis (m-phenylene)-26-crown-8 Derivatives

Carbon monoxide is a colorless and odorless gas,which can easily combine with the prosthetic group of heme on hemoglobin to cause poisoning of organisms.It is known as the"silent killer".The human body has no obvious stress response to carbon monoxide,so it is often difficult for people with carbon monoxide poisoning to detect their symptoms.Therefore,the rapid and convenient detection of carbon monoxide concentration in the environment has become an important research topic.On the other hand,the construction of supramolecular assemblies with excellent stimulus responsiveness and controllability through host-guest interactions is a research hotspot in supramolecular chemistry.Crown ethers,as the first-generation macrocyclic molecules,are a class of host compounds that are relatively mature and have received much attention at present.They are widely used due to their simple synthesis,unique structure,easy derivatization,stable chemical properties and excellent molecular recognition performance field of supramolecular chemistry.In this paper,two bis(m-phenylene)-26-crown-8 derivatives were first designed and synthesized,and carbon monoxide probes were constructed based on the cyclopalladium metal complex formed by crown ether derivatives and palladium acetate,and ammonium salt molecules were introduced through host-guest interaction.The detection performance of the probe for carbon monoxide was further improved;in addition,In addition,two kinds of Schiff base derivatives containing phenolic hydroxyl group of bis(m-phenylene)-26-crown-8 were designed and synthesized,and their specific response behaviors to metal ions were explored.Specific content includes:(1)First,the methods and research progress of carbon monoxide detection and the research status of supramolecular chemistry and the construction of functional organic supramolecular assemblies are reviewed in this paper.(2)Design and synthesis of bis(m-phenylene)-26-crown-8-dicarboxylate N-benzyl piperidinol ester and secondary ammonium salt guest molecule,using ¹H NMR,¹³C NMR and mass spectrometry to analyze these two compounds and the structures of important intermediates were characterized,and the complexation and assembly behavior between host and guest were studied,and the detection ability of the supramolecular assembly for carbon monoxide was preliminarily explored.(3)The benzo[a]phenazinone derivatives and viologen salt guest molecules of bis(m-phenylene)-26-crown-8 were designed and synthesized,and the two compounds and important intermediates were analyzed by ¹H NMR,¹³C NMR and mass spectrometry.The structure was characterized,and the complexation and assembly behavior between host and guest were studied.The responsiveness of supramolecular assemblies to carbon monoxide was further explored.The experimental results show that the assembly can achieve a remarkable response to 1%carbon monoxide atmosphere in a short time.(4)Design and synthesis of bis(m-phenylene)-26-crown-8 benzo[a]phenazinone derivatives with extended carbon chains and two bis(m-phenylene)-26-crown-8 Schiff base derivatives containing phenolic hydroxyl groups.The structures of the two and important intermediates were characterized by ¹H NMR,¹³C NMR and mass spectrometry,and explored their response behaviors to various metal ions by UV and fluorescence spectroscopy,and determined their detection limits for several specific metal ions.