葫芦脲超分子包结物的构建及性能研究
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摘要
超分子化学近年来发展十分迅速,因为其在功能材料、催化化学、生物医药、信息存储等诸多方面有着巨大的潜在应用而备受科学家们的瞩目。主客体化学是主体与客体之间通过非共价键的形式相互作用在一起而形成包结物的超分子化学,其中以具有疏水内腔的大环化合物葫芦脲为主体的主客体包结物是近年来主客体化学领域的研究热点之一。葫芦脲是由甘脲缩合而得,其两端口由羰基组成,这种具有很强刚性的空腔大环化合物因为其具有与阳离子或者带正电基团形成稳定包结物的能力,而被认为是构造超分子包结物的明星分子。
本文围绕着用葫芦脲构造功能性的超分子包结物为目标而展开,具体内容如下：
第一章,简述了主客体化学的研究进展,并综述了基于葫芦脲为主体的主客体化学的研究动态。
第二章,本章设计合成了由对2-[2-[4-(二甲氨基)苯基]乙烯基]吡啶盐(DMA)和对氨基苯氧基乙基(OA)组成的V型菁染料分子DP。
1、考察了CB[7]与DP分子形成[2]拟轮烷的过程。因为空间位阻,CB[7]只能同时与其中一端包结,在pH控制的条件下CB[7]可以在OA和DMA之间相互转化,并能引起溶液颜色的改变。并通过核磁共振氢谱证明了这两种状态的包结构象。除此之外,又计算了葫芦脲的包结对客体分子DP的pKa的影响。
2、考察了DP与CB[8]之间包结作用,用一维、二维核磁共振氢谱、质谱以及吸收光谱等手段确定了DP与CB[8]之间的包结构象,并计算了包结常数。并且对比了Y-环糊精、CB[8]与DP的包结能力,并计算了Y-环糊精与DP分子的包结常数。
第三章,设计合成了一个含有菁染料单元的客体分子LDP,此分子的两个识别点可以与CB[7]包结在一起。通过核磁,质谱和光谱等手段揭示了CB[7]与LDP包结形成拟轮烷CB[7]·LDP和CB[7]2-LDP的构型,并通过光谱数据,计算了CB[7]的包结而引起客体分子氨基pKa值的变化。
第四章,以合成基于葫芦脲为主体的荧光轮烷为目标,进行了不断的探索,先后设计了不同结构的轮烷R1、R2、R3、R4、R5、R6。
1、设计了以三聚乙二醇作为连接发色团和控制基团的长链而设计了不同结构的轮烷R1、R2、R3。其中轮烷R1以蒽的衍生物作为荧光输出端,异酞酸作为驱动控制端；轮烷R2以三苯胺衍生物作为荧光输出端,且以异酞酸作为驱动控制端；轮烷R3以三苯胺衍生物作为荧光输出端,以烟酰胺作为控制端；分别通过几种不同的合成路线探索了荧光轮烷R1、R2、R3的合成,但终因反应物的溶解度太小、没有合适溶剂、聚乙二醇链的亲水性等原因导致最终合成失败。
2、总结之前失败的原因,用纯烷基链代替了聚乙二醇而重新设计了轮烷R4。在最后一步卤代烷与烟酰胺反应组装形成轮烷R4的合成反应中,因反应物的水溶性不好,而导致最后一步反应失败。
3、为了改善因为反应物水溶性太差而导致的反应失败,引进了溶解性好于三苯胺醛的4-二甲胺基苯甲醛作为荧光输出基团的底物,由此而设计出了荧光轮烷R5。但在最终组装合成轮烷的反应中,反应物在水中溶解度并未得到有效改善,而导致轮烷R5合成失败。
4、以轮烷R4的客体分子(即两端含有阻挡基团的哑铃型分子)为基础,采用空腔和端口尺寸比CB[6]大的化合物CB[7]作为主体分子,以期待用滑动的方法获得轮烷R6。但因在最后提纯过程中产物与反应物难以分离,而导致合成失败。
第五章结论
Supramolecular chemistry with rapid developing has been attracted the attention of the chemists for its vast potential application in functional materials, catalyst chemistry, medicine and data storage. In supramolecular chemistry, host-guest chemistry describes complex that are composed of host and guest that are held together by noncovalent bonds. One of the most popular hosts is cucurbituril with hydrophobic cavity macrocyclic compound. The host-guest complex based on cucurbituril received much attention. Cucurbituril is consisting of several glycoluril repeat units. The rigid cage like compound prefers to bind with cation and positive group and can form a stable complex which is regarded as a highlight molecular.
Our research surrounds the constructing functional supramolecular complex based on cucurbiturils. Details as show:
Chapter1, the research development of supramolecular chemistry and cucurbiturils are introduced.
Chapter2. A new V-type cyanine molecular with two recognition points (OA and DMA) was synthesized. CB[7] will bind one of the two sides simultaneously only for the steric hindrance. CB[7] can switch between the two moieties accompanying the color change by adjusting the pH of solution.1H-NMR was carried out for disclosing the conformation of the two states. In addition, one and two dimensional H-NMR, ESI-MS and absorption spectra were taken advantaged to investigate the configuration of V-type molecule and CB[8].
Chapter3. A new guest LDP was synthesized which contains a cyanine unit. There are two recognition points can bind with CB[7].1H-NMR, ESI-MS and absorption spectra were carried out to disclose the conformation of [2]pseudorotaxane CB[7]·LDP and [3]pseudorotaxane CB[7]2·LDP.
Chapter4, our goal is synthesis of fluorescent rotaxane based on cucurbituril. Different structure rotaxanes R1, R2, R3, R4, R5, and R6were designed and tried synthesis.
1, the rotaxanes R1, R2and R3were devised with the same connection group: oligomeric ethylene glycol. R1is composing of anthracene and5-aminoisophthalic acid which are utilized to as a fluorescence output moiety and controllable moiety respectively. But the reaction is failed for the low solubility of the reactant. The rotaxane R2are designed by using the triphenylamine as the fluorescence output moiety and5-aminoisophthalic acid as controllable moiety. The rotaxane R3are designed by using the triphenylamine as the fluorescence output moiety and niacinmide as controllable moiety. The result was failed for the little solubility of reactants and hydrophilic oligomeric ethylene glycol chain.
2. A pure decyl chain as a new bridge was introduced to join the functional and controllable group. The low solubility of intermediate was the reason for the failure at the last step for synthesizing rotaxane R4.
3. To improve the solubility of reactant,4-dimethylaminobenzaldehyde was introduced as fluorescence moiey. But the reactant solubility wasn't increased efficiently, so the synthesis of rotaxane R5was failure.
4. The bigger host compound CB[7] was introduced for instead of CB[6]. At last, we didn't get the pure rotaxane R6because we can't separate it from the products.
Chapter5is the conclusion.
本文围绕着用葫芦脲构造功能性的超分子包结物为目标而展开,具体内容如下：
第一章,简述了主客体化学的研究进展,并综述了基于葫芦脲为主体的主客体化学的研究动态。
第二章,本章设计合成了由对2-[2-[4-(二甲氨基)苯基]乙烯基]吡啶盐(DMA)和对氨基苯氧基乙基(OA)组成的V型菁染料分子DP。
1、考察了CB[7]与DP分子形成[2]拟轮烷的过程。因为空间位阻,CB[7]只能同时与其中一端包结,在pH控制的条件下CB[7]可以在OA和DMA之间相互转化,并能引起溶液颜色的改变。并通过核磁共振氢谱证明了这两种状态的包结构象。除此之外,又计算了葫芦脲的包结对客体分子DP的pKa的影响。
2、考察了DP与CB[8]之间包结作用,用一维、二维核磁共振氢谱、质谱以及吸收光谱等手段确定了DP与CB[8]之间的包结构象,并计算了包结常数。并且对比了Y-环糊精、CB[8]与DP的包结能力,并计算了Y-环糊精与DP分子的包结常数。
第三章,设计合成了一个含有菁染料单元的客体分子LDP,此分子的两个识别点可以与CB[7]包结在一起。通过核磁,质谱和光谱等手段揭示了CB[7]与LDP包结形成拟轮烷CB[7]·LDP和CB[7]2-LDP的构型,并通过光谱数据,计算了CB[7]的包结而引起客体分子氨基pKa值的变化。
第四章,以合成基于葫芦脲为主体的荧光轮烷为目标,进行了不断的探索,先后设计了不同结构的轮烷R1、R2、R3、R4、R5、R6。
1、设计了以三聚乙二醇作为连接发色团和控制基团的长链而设计了不同结构的轮烷R1、R2、R3。其中轮烷R1以蒽的衍生物作为荧光输出端,异酞酸作为驱动控制端；轮烷R2以三苯胺衍生物作为荧光输出端,且以异酞酸作为驱动控制端；轮烷R3以三苯胺衍生物作为荧光输出端,以烟酰胺作为控制端；分别通过几种不同的合成路线探索了荧光轮烷R1、R2、R3的合成,但终因反应物的溶解度太小、没有合适溶剂、聚乙二醇链的亲水性等原因导致最终合成失败。
2、总结之前失败的原因,用纯烷基链代替了聚乙二醇而重新设计了轮烷R4。在最后一步卤代烷与烟酰胺反应组装形成轮烷R4的合成反应中,因反应物的水溶性不好,而导致最后一步反应失败。
3、为了改善因为反应物水溶性太差而导致的反应失败,引进了溶解性好于三苯胺醛的4-二甲胺基苯甲醛作为荧光输出基团的底物,由此而设计出了荧光轮烷R5。但在最终组装合成轮烷的反应中,反应物在水中溶解度并未得到有效改善,而导致轮烷R5合成失败。
4、以轮烷R4的客体分子(即两端含有阻挡基团的哑铃型分子)为基础,采用空腔和端口尺寸比CB[6]大的化合物CB[7]作为主体分子,以期待用滑动的方法获得轮烷R6。但因在最后提纯过程中产物与反应物难以分离,而导致合成失败。
第五章结论
Supramolecular chemistry with rapid developing has been attracted the attention of the chemists for its vast potential application in functional materials, catalyst chemistry, medicine and data storage. In supramolecular chemistry, host-guest chemistry describes complex that are composed of host and guest that are held together by noncovalent bonds. One of the most popular hosts is cucurbituril with hydrophobic cavity macrocyclic compound. The host-guest complex based on cucurbituril received much attention. Cucurbituril is consisting of several glycoluril repeat units. The rigid cage like compound prefers to bind with cation and positive group and can form a stable complex which is regarded as a highlight molecular.
Our research surrounds the constructing functional supramolecular complex based on cucurbiturils. Details as show:
Chapter1, the research development of supramolecular chemistry and cucurbiturils are introduced.
Chapter2. A new V-type cyanine molecular with two recognition points (OA and DMA) was synthesized. CB[7] will bind one of the two sides simultaneously only for the steric hindrance. CB[7] can switch between the two moieties accompanying the color change by adjusting the pH of solution.1H-NMR was carried out for disclosing the conformation of the two states. In addition, one and two dimensional H-NMR, ESI-MS and absorption spectra were taken advantaged to investigate the configuration of V-type molecule and CB[8].
Chapter3. A new guest LDP was synthesized which contains a cyanine unit. There are two recognition points can bind with CB[7].1H-NMR, ESI-MS and absorption spectra were carried out to disclose the conformation of [2]pseudorotaxane CB[7]·LDP and [3]pseudorotaxane CB[7]2·LDP.
Chapter4, our goal is synthesis of fluorescent rotaxane based on cucurbituril. Different structure rotaxanes R1, R2, R3, R4, R5, and R6were designed and tried synthesis.
1, the rotaxanes R1, R2and R3were devised with the same connection group: oligomeric ethylene glycol. R1is composing of anthracene and5-aminoisophthalic acid which are utilized to as a fluorescence output moiety and controllable moiety respectively. But the reaction is failed for the low solubility of the reactant. The rotaxane R2are designed by using the triphenylamine as the fluorescence output moiety and5-aminoisophthalic acid as controllable moiety. The rotaxane R3are designed by using the triphenylamine as the fluorescence output moiety and niacinmide as controllable moiety. The result was failed for the little solubility of reactants and hydrophilic oligomeric ethylene glycol chain.
2. A pure decyl chain as a new bridge was introduced to join the functional and controllable group. The low solubility of intermediate was the reason for the failure at the last step for synthesizing rotaxane R4.
3. To improve the solubility of reactant,4-dimethylaminobenzaldehyde was introduced as fluorescence moiey. But the reactant solubility wasn't increased efficiently, so the synthesis of rotaxane R5was failure.
4. The bigger host compound CB[7] was introduced for instead of CB[6]. At last, we didn't get the pure rotaxane R6because we can't separate it from the products.
Chapter5is the conclusion.
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