Synthesis And Application Of Supramolecular Macrocycle

Molecular recognition and assembly are two basic cores of supramolecular chemistry.Molecules inside the supramolecular system interact via non-colavent bonds.Supramolecular chemistry functional systems based on host-guest interaction have had great performances and broad prospects in the field of drug delivery systems and artificial intelligent materials.As we know a new type of macrocyclic molecule pillararene was discoverd in 2008,due to its highly symmetrical rigid ring structure and excellent derivatization ability,supramolecular chemistry functional systems which were constructed by pillar[5]arene or pillar[6]arene have always been a hot topic in the filed of science.In this paper,two kinds of supramolecular chemistry functional systems with multiple response properties were built based on pillararene,and the synthesis of a new type of oxyheterocyclic macrocycle was preliminarily studied.This thesis will be divided into the following three parts:1.Construction of vesicles with photodegradation based on water-soluble pillar[5]arene and anthracene derivativesThe guest molecule G:9,10-dialkoxyanthracene was successfully synthesized.The anthracene unit can capture the single state oxygen to form the internal oxide.WP5 and molecule G could form supramolecular amphiphile in water system based on host-guest interaction,then further self-assemble into vesicles.The binding mode between WP5 and molecule G,particle size and morphology of the vesicles were characterized by various testing methods.Supramolecular assemblies exhibited enhanced photodegradability after UV irradiation compared with single molecule G.Supramolecular assemblies co-assembled with eosin Y could be photodegraded under visible light,which has showed great ability in vitro controlled drug release with pH response and photodegradation response2.Construction of pH responsive dispersant of graphene oxide aqueous solution based on host-guest interaction between water-soluble pillar[6]arene and ferroceneFirst of all,guest molecule Py-Fc(pyrene modified by ferrocene)was synthesized.Throught the ?-? accumulation force between graphene oxide and pyrene and the host-guest interaction between pillar[6]arene and ferrocene,WP6 was successfully loaded on the surface of graphene oxide which work as a aqueous dispersant.This supramolecular chemistry functional system could effectively inhibit the aggregation of graphene oxide layers in high temperature and keep the homogeneity of the graphene oxide solution.In addition,this system possessed a pH response performance.Graphene oxide can rapidly precipitate without order.The successful construction of this supramolecular chemistry functional system has a certain reference value for the homogeneous dispersion of graphene and its derivative in aqueous system.It also may have potential applications in pH detection and sewage disposal.3.Synthesis of new oxyheterocyclic macrocycleWe designed the synthetic routin of a new kind oxyheterocyclic macrocycle with rigid skeleton and electron-rich cavity,which has the potential for subsequent chemical modification to construct banded heterocyclic aromatics.F irstly,the template reaction was completed with 3,6-two chlorine-2,5-two methyl formate-1,4-benzoquinone and phenol,which provided a certain experimental basis for synthesis of our target product.Secondly,the synthesis conditions of oxyheterocyclic macrocycle were preliminarily screened,which may provide certain reference value for subsequent synthesis...