Chiral Regulalation Of Water-soluble Pillar[5]arene And Synthesis Of Aromatic Macrocycle CTX

Supramolecular chemistry is an important part of chemistry subject,which is focused on self-assembly through weak intermolecular interactions,including hydrogen bonds,coordination and?-?interactions,etc.With the development of supramolecular chemistry,researchers have synthesized various kinds of supramolecular macrocyclic host molecules,and constructed a series of supramolecular functional systems based on the host-guest interaction between the macrocyclic host and specific guest molecules,which have a wide range of application values in chirality recognition,etc.This thesis focuses on the study of supramolecular macrocycles,a system for redox-induced of amino acid derivatives chiral inversion process of water-soluble pillar[5]arene WP5 was constructed,which based on the unique dynamically racemic planar chirality and excellent host-guest recognition ability of novel macrocycle molecule pillar[5]arene.In addition,the synthesis of a new type of supramolecular macrocycle was studied in this paper.The research content of the thesis mainly includes two parts:In the first part,based on previous work of our group,we constructed a system of chiral inversion process of WP5.L-Cys-OMe and L-Cy SS-OMe can induce p R-WP5and p S-WP5 in aqueous solution,respectively.Under the driving of dithiothreitol(DTT)/hydrogen peroxide(H₂O₂),L-Cys-OMe and L-Cy SS-OMe interconverted with each other and induced the chiral conformation reversal of WP5 as the reaction went on.By reading the CD signals,the chiral conformational change of WP5 can be easily observed.This chiral reversal strategy by redox reactions can be further applied to the construction of intelligent chiral switching materials.In the second part,we synthesized a new type of supramolecular macrocyclic host cyclotrixylohydroquinoylene(CTX)by one-pot and high yield reaction of 2,3-dimethylhydroquinone and formaldehyde catalyzed by HCl.Then the reaction conditions for the synthesis of CTX were optimized,the experiment proved that the target compound can be obtained under a variety of reaction conditions.Next,we modified it and obtained a series of CTX derivatives to further expanding this class of supramolecular macrocycle.In addition,we also selected other substrates as starting materials and studied the possibility of their ring formation.Due to the facile synthesis,easy modification and unique censer-shaped structures of CTX,it is expected to have good applications value in molecular ion recognition,liquid crystal and so forth.In summary,the supramolecular macrocycles were taken as the research theme in this paper.Firstly,the interconversion of amino acid derivatives by redox actions was used to realize the chiral reversal of the conformational chirality of racemic water-soluble pillar[5]arene,which provides a new idea for the study of dynamic chiral reversal at the monomolecular level.In addition,In addition,a novel supramolecular macrocycle and various derivatives were synthesized,further enriching the supramolecular chemistry.It hoped that the research in this thesis will provide a reference for the study of supramolecular macrocyclic chirality and synthesis of supramolecular macrocycles.