Synthesis Of Phenolic Condensation Macrocyclic Compounds And Their Host-guest Recognition

Every rapid development of supramolecular chemistry is inseparable from a variety of macrocycle,from crown ether,cyclodextrin,calixarenes,cucurbituril to pillararenes,and then to leaning pillar[6]arene,bowtiearene,pagoda[4]arene,prismarenes and so on.These macrocycle compounds not only have special structures,but also are easy to synthesize,derive and rich in value electron cavities and various properties make them widely used in various fields.Therefore,the synthesize of new macrocycle compounds is of great significance to the development of supramolecular chemistry.Based on this,two new types of macrocycle compounds were synthesized and their host-guest interactions were attempted.This thesis mainly includes the following two parts: Part 1.The mixture of p-(methoxy)calix[n]arenes(n = 6,7,or 8)and paraformaldehyde was prepared in one step from p-methoxyphenol under basic conditions,and their fully methylated derivatives p-(dimethyloxy)calix[n]arenes(n = 6,7,or 8)were also prepared and purified by column chromatography to indentify their structures.In this process,the single crystal of p-(dimethyloxy)calix[7]arene was obtained and its structure was confirmed.The proportion of p-(methoxy)calix[6]-,[7]-,and [8]-arenes in the mixture obtained from the reaction was investigated under different reaction conditions,and p-(methoxy)calix[6]-and [8]-arenes could be separated from the mixture by solvent extraction.In addition,the host-guest interaction of p-(dimethyloxy)calix[6]arene with methyl-4,4?-bipyridinium hexafluorophosphate in organic solvents was investigated.Part 2.Using tetra-substituted o-xylohydroquinone and formaldehyde hydrate as a raw material,its trimer compound cyclotrixylohydroquinoylene(CTX)can be obtained under acidic conditions.The hydroquinone is bridged by methylene,and the upper edge of the obtained compound is directly oxidized.The obtained water-soluble cyclotrixylohydroquinoylene derivative(WCTX[CH2])can interact with amethyst to form host-guest complex with a complex constant of(9.92 ± 2.79)× 103 M-1.This new cyclotriveratrylene(CTV)analogue has the advantages of simple synthesis process,high yield,no other by-products,no purification and easy modification.The macrocycle and its water-soluble derivatives well combine the characteristics of traditional cyclotriveratrylene,resorcinarenes and water-soluble pillararenes,and can be widely used in supramolecular chemistry fields such as molecular recognition,catalysis,drug delivery,artificial light collection and so on.