环糊精及其共轭体的纳米超分子体系的构筑及功能研究
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摘要
在本文的工作中,我们选择了环糊精,葫芦脲,卟啉,杯芳烃四种超分子主体作为研究对象,利用各自的特点,设计出几种功能性的超分子组装体。论文的主要内容和创新点如下:
1.合成了一种基于修饰环糊精和葫芦脲的假轮烷。接着,这种假轮烷穿入PPG2000的高分子链中形成一种二维假聚轮烷。这个二维假聚轮烷通过FT-IR,NMR,TG-DTA,元素分析和透射电镜表征。特别的是,这个二维假聚轮烷可以在碱的存在下解离成一维假聚轮烷。再加入alfa环糊精后可以在pH调控下实现杂环糊精二维假聚轮烷和环糊精-葫芦脲假聚轮烷之间转换。
2.研究了含有不同数量葫芦脲于侧臂的二维假聚轮烷对DNA的凝聚行为,发现穿入侧臂的葫芦脲的数量严格影响对DNA的凝聚效果。
3.研究了在click chemistry应用在修饰环糊精中,催化剂Cu(I)的用量对反应的影响。
4.通过click chemistry的方法合成了卟啉-β-CD或卟啉-全甲基-β-CD两种环糊精-卟啉共轭体。通过和中位.四苯基卟啉-4,4',4”,4”'-四磺酸钠(3)作用,可以得到两种形态完全不同的组装体。这两种组装体分别以纳米棒状结构和纳米网状结构呈现。通过一系列表征发现,主客体之间的键合强度以及主体自身的构象变化是导致这种差异的主要原因。
5.合成了两亲的环糊精-杯芳烃共轭体。它们在不同溶剂下能以不同的组装形态形成聚集体。这种聚集体的形态变化可以通过溶剂的极性来进行调控。
6.结合双胺基修饰gama环糊精和高氯酸铜,获得了第一个对于2-蒽酸光二聚环加成反应的非敏化催化超分子光不对称合成的例子。在甲醇和水的混合溶剂中在-50℃下可以对anti-head-to-head环加成产物以高达70%的ee和52%的产率获得。这都是目前报道的环糊精诱导光手性催化的最好效果。
In the thesis,we chose cyclodextrins,cucurbiturils,porphyrins and calixarenes as the basic building blocks to contruct supramolecular functional aggregations and nano reactor container for photochirogeneis,which are summarized as follows:
1.A pseudorotaxane was synthesized by reaction of cucurbit uril with 6-[(6-aminohexyl)amino]-6-deoxy-beta-cyclodextrin chloride.Subsequently, pseudorotaxanes were further assembled to form a 2D pseudopolyrotaxane through an alpha,omega-PPG2000 diamino polymer threading the cavities of cyclodextrins,and the resulting pseudopolyrotaxane was comprehensively characterized by FT-IR, NMR,TG-DTA,elemental analysis,and transmission electron microscopy. Significantly,the 2D pseudopolyrotaxane can turn into a main-chain pseudopolyrotaxane in the presence of base,and then the addition of alpha-cyclodextrins may result in a reversible switch between two different 2D pseudopolyrotaxanes.
2.2D pseudopolyrotaxanes containing beta-cyclodextrins and cucurbit urils can induce DNA condensation,and the number of cucurbit urils threaded onto the side chains of beta-cyclodextrins plays important roles in this process.
3.Tetrakis(permethyl-beta-cyclodextrin)-modified zinc(Ⅱ) porphyrin(1) and tetra(beta-cyclodextrin)-modified zinc(Ⅱ) porphyrin(2) were synthesized via "click chemistry".Intermolecular inclusion complexation of these structurally similar 1 and 2 with tetrasodium tetraphenylporphyrintetrasulfonate(3) led to formation of two distinctly different nanoarchitectures with alternate porphyrin and cyclodextrin arrays, which were proven to be network and nanorod aggregates,respectively,by using transmission electron microscopy,atomic force microscopy,and scanning electron microscopy.From the results of comparative studies in different solutions,we elucidated the mechanisms that result in nanorod to network aggregates transition, concluding that the complexation strength of porphyrin with cyclodextrin is a crucial factor to activate the potential binding sites of a molecular building block.
4.Two new beta-cyclodextrins(beta-CDs) modified with chromophore were synthesized in high yields through Huisgen 1,3-dipolar cycloaddition.The amount of Cu catalyst was demonstrated to be a key factor that determines the yield of the 1,3-dipolar cycloaddition when applied to CD derivatization.While a catalytic amount of Cu-catalyst is commonly required in conventional click chemistry,more than a half equivalent of Cu catalyst was desirable for obtaining the modified CDs in satisfactory yields.
5.Amphiphilic cyclodextrin-calixarene conjugates can self-assembly to form distinctly different aggregations,and the morphology of aggregations critically relys on the polarity and hydrophilicity of solvent.
6.Combined use of diamino-γ-cyclodextrin and Cu(ClO_4)_2 achieved the first "catalytic" supramolecular photochirogenesis in the photocyclodimerization of 2-anthracenecarboxylate in aqueous methanol solution at -50℃to give the anti-head-to-head cyclodimer of 70%enantiomeric excess in 52%yield,both of which are the highest ever reported for CD-mediated photochirogenesis.
1.合成了一种基于修饰环糊精和葫芦脲的假轮烷。接着,这种假轮烷穿入PPG2000的高分子链中形成一种二维假聚轮烷。这个二维假聚轮烷通过FT-IR,NMR,TG-DTA,元素分析和透射电镜表征。特别的是,这个二维假聚轮烷可以在碱的存在下解离成一维假聚轮烷。再加入alfa环糊精后可以在pH调控下实现杂环糊精二维假聚轮烷和环糊精-葫芦脲假聚轮烷之间转换。
2.研究了含有不同数量葫芦脲于侧臂的二维假聚轮烷对DNA的凝聚行为,发现穿入侧臂的葫芦脲的数量严格影响对DNA的凝聚效果。
3.研究了在click chemistry应用在修饰环糊精中,催化剂Cu(I)的用量对反应的影响。
4.通过click chemistry的方法合成了卟啉-β-CD或卟啉-全甲基-β-CD两种环糊精-卟啉共轭体。通过和中位.四苯基卟啉-4,4',4”,4”'-四磺酸钠(3)作用,可以得到两种形态完全不同的组装体。这两种组装体分别以纳米棒状结构和纳米网状结构呈现。通过一系列表征发现,主客体之间的键合强度以及主体自身的构象变化是导致这种差异的主要原因。
5.合成了两亲的环糊精-杯芳烃共轭体。它们在不同溶剂下能以不同的组装形态形成聚集体。这种聚集体的形态变化可以通过溶剂的极性来进行调控。
6.结合双胺基修饰gama环糊精和高氯酸铜,获得了第一个对于2-蒽酸光二聚环加成反应的非敏化催化超分子光不对称合成的例子。在甲醇和水的混合溶剂中在-50℃下可以对anti-head-to-head环加成产物以高达70%的ee和52%的产率获得。这都是目前报道的环糊精诱导光手性催化的最好效果。
In the thesis,we chose cyclodextrins,cucurbiturils,porphyrins and calixarenes as the basic building blocks to contruct supramolecular functional aggregations and nano reactor container for photochirogeneis,which are summarized as follows:
1.A pseudorotaxane was synthesized by reaction of cucurbit uril with 6-[(6-aminohexyl)amino]-6-deoxy-beta-cyclodextrin chloride.Subsequently, pseudorotaxanes were further assembled to form a 2D pseudopolyrotaxane through an alpha,omega-PPG2000 diamino polymer threading the cavities of cyclodextrins,and the resulting pseudopolyrotaxane was comprehensively characterized by FT-IR, NMR,TG-DTA,elemental analysis,and transmission electron microscopy. Significantly,the 2D pseudopolyrotaxane can turn into a main-chain pseudopolyrotaxane in the presence of base,and then the addition of alpha-cyclodextrins may result in a reversible switch between two different 2D pseudopolyrotaxanes.
2.2D pseudopolyrotaxanes containing beta-cyclodextrins and cucurbit urils can induce DNA condensation,and the number of cucurbit urils threaded onto the side chains of beta-cyclodextrins plays important roles in this process.
3.Tetrakis(permethyl-beta-cyclodextrin)-modified zinc(Ⅱ) porphyrin(1) and tetra(beta-cyclodextrin)-modified zinc(Ⅱ) porphyrin(2) were synthesized via "click chemistry".Intermolecular inclusion complexation of these structurally similar 1 and 2 with tetrasodium tetraphenylporphyrintetrasulfonate(3) led to formation of two distinctly different nanoarchitectures with alternate porphyrin and cyclodextrin arrays, which were proven to be network and nanorod aggregates,respectively,by using transmission electron microscopy,atomic force microscopy,and scanning electron microscopy.From the results of comparative studies in different solutions,we elucidated the mechanisms that result in nanorod to network aggregates transition, concluding that the complexation strength of porphyrin with cyclodextrin is a crucial factor to activate the potential binding sites of a molecular building block.
4.Two new beta-cyclodextrins(beta-CDs) modified with chromophore were synthesized in high yields through Huisgen 1,3-dipolar cycloaddition.The amount of Cu catalyst was demonstrated to be a key factor that determines the yield of the 1,3-dipolar cycloaddition when applied to CD derivatization.While a catalytic amount of Cu-catalyst is commonly required in conventional click chemistry,more than a half equivalent of Cu catalyst was desirable for obtaining the modified CDs in satisfactory yields.
5.Amphiphilic cyclodextrin-calixarene conjugates can self-assembly to form distinctly different aggregations,and the morphology of aggregations critically relys on the polarity and hydrophilicity of solvent.
6.Combined use of diamino-γ-cyclodextrin and Cu(ClO_4)_2 achieved the first "catalytic" supramolecular photochirogenesis in the photocyclodimerization of 2-anthracenecarboxylate in aqueous methanol solution at -50℃to give the anti-head-to-head cyclodimer of 70%enantiomeric excess in 52%yield,both of which are the highest ever reported for CD-mediated photochirogenesis.
引文
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