Synthesis Of Ferrocenyl Chiral Sulfoxide And Ferrocenyl 1,2,3-triazole And Study On Ion Recognition Properties Of 1,2,3-triazole

In this thesis,we have mainly studied the synthesis of two series of ligands containing ferrocenyl group.In the first part,we synthesized a series of ferrocenyl1,2,3-triazole compounds and applied them as chemosensors to detect metal ions.In the second part,we synthesized a series of chiral sulfoxides containing ferrocenyl group.The details of the two parts are as follows:In the first part,iodide I₂ was used to catalyze the reaction of ferrocenyl hydrazone with aniline to synthesize new ferrocenyl 1,2,3-triazole ligands.By optimizing the reaction conditions,the yield of the target product was increased to83%and the optimized reaction conditions were obtained.The catalyst was I₂,the oxidant was AIBN,and the solvent was EA.Through substrate screening,it was proved that the reaction was suitable for a wide range of substrates,high efficiency,green,simple,safe and avoided the use of metal catalysts and azide.Meanwhile,the starting material was easy to get.The series of ferrocenyl 1,2,3-triazole ligands were characterized by NMR,HRMS and single crystal diffraction.Then,we selected 3b,3j and 3t ligands as chemosensors to detect metal ions.The results showed that 3b could selectively recognize Cu²⁺and Pb²⁺,3j and 3t could recognize Cu²⁺selectively.The Cu²⁺recognition of the three ligands was visible to the naked eye,and the color of ligand solution changed from yellow to atrovirens.All three ligands could detect metal ions by UV-Vis spectra and CV,DPV.In the second part,the asymmetric catalytic oxidation of 1-substituted ferrocenyl p-toluene sulfide with manganese catalyst and porphyrin-like chiral ligand was studied.A chiral ferrocenyl sulfoxide ligand was synthesized by introducing the stereoscopic configuration determination sulfoyl group?>S⁺—O^-?.The optimized conditions were determined by screening,the catalyst was Mn?OTf?₂?1.0 mol%?,the ligand was porphyrin-like ligand L₁?1.0 mol%?,the solvent was CH₂Cl₂/IPA?3ml,1:1?,and the oxidant was H₂O₂,which was safe and green.Although the result could only reach a moderate level and obtained sulfoxide in 53%yield,the enantioselectivity of sulfoxide was 64%,however,it was found that the enantioselectivity of ferrocenyl p-fluorobenzene sulfoxide could be increased to 84%by changing the substrate.The reaction was simple and safe,and the starting material was easy to obtain.Moreover,this reaction successfully overcame the difficulty of asymmetric oxidation of large steric sulfides.These series of sulfoxide ligands were characterized.by NMR,HRMS,single crystal diffraction and HPLC.