Synthesis And Anion Recognition Of Phenolic Hydroxyl Macrocycle

Due to the importance of anion recognition in the fields of life and environment,the design and synthesis of novel anion receptors and their research in host-guest chemistry have been active research areas.In recent years,our research group has established a certain research foundation in the synthesis,recognition and non-covalent interaction of supramolecular assembly about macrocyclic compounds containing phenolic hydroxyl groups and amide groups.In this paper,N,N'-?3-aminophenyl?-2,6-dicarboximide pyridine?1?and 5,5'-methylenebissalicylic aldehyde?2?were prepared by condensation reaction to obtain rigid[1+1]Schiff base macrocycle L¹ containing phenolic hydroxyl group.Then,the C=N double bond of Schiff base in L¹ is reduced to obtain a saturated macrocycle L² with a more flexible ring skeleton,which is further used for the comparative investigation of bond cooperation between a series of anions.The main research work of this paper is as follows:1.Macrocycle L¹ and L² containing phenolic hydroxyl group were synthesized and their structures were respectively characterized by 1H NMR,MS and elemental analysis,and the crystal structures of macrocycle L¹ and L² were obtained.2.The recognition ability of L¹ with series of anion was investingated by UV-Vis absorption spectra technique.The results showed that L¹ displayed a obvious recognition for AcO^-?HSO₄^-?H₂PO₄^-?H₂P₂O₇^2-?HP₂O₇^3-,and the study of the reaction between the macrocyclic compound L² with AcO^-?HSO₄^-?H₂PO₄^-?H₂P₂O₇^2-?HP₂O₇^3-was surveyed by ¹H NMR;furthermore,the ITC technology was used to reveal the thermodynamic origin of the recognition of macrocycles and anions.3.The recognition ability of L² with series of anion was investingated by UV-Vis absorption spectra technique.the results showed that L² displayed a obvious recognition for AcO^-?H₂PO₄^-?H₂P₂O₇^2-?HP₂O₇^3-,and the study of the reaction between the macrocyclic compound L² with AcO^-?H₂PO₄^-?H₂P₂O₇^2-?HP₂O₇^3-was surveyed by ¹H NMR.