基于冠醚和葫芦脲构筑的复杂轮烷和准轮烷
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摘要
基于大环主体及其相应的客体分子构筑轮烷和准轮烷是超分子化学的一个重要研究方向,通过对轮烷和准轮烷结构和功能的研究不仅能够促进对非共价相互作用的了解,还可有力地推动分子机器和纳米科学等研究领域的发展。本文采用冠醚和葫芦脲两类大环主体,分别针对其在有机相和水相中对特定的阳离子客体所具有的键合能力,设计并构筑了一系列新颖的轮烷和准轮烷结构,并研究了其在特定刺激下的响应行为。具体内容如下：
1.首先简要介绍了超分子化学的研究概况,对基于冠醚和葫芦脲构筑的轮烷和准轮烷体系所取得的最新成果进行了综述。
2.基于冠醚/二级胺主客体作用构筑了两种含有炔和叠氮基团的准轮烷,进而通过click反应将其共价连接合成了一种双轴杂[7]轮烷。在该轮烷中外侧的苯环可以封端21冠7环组分,又可以继续封端中心的34冠10环组分。该研究的创新之处在于这种以稳定的超分子配合物作为反应模块的策略,不仅简化了传统的穿线封端方法复杂的合成步骤,而且可以精确控制轮烷结构中两种环状组分的位置。该研究为有机超分子化学的发展提供了一种模块化的构筑策略,可用于构筑具有独特结构和功能的复杂机械互锁分子。
3.合成了一系列含有不同修饰基团的苯乙烯吡啶和联吡啶衍生物,并研究了这两类有机阳离子客体与葫芦[7]脲、葫芦[8]脲以及α-环糊精等大环主体的组装行为。
4.通过葫芦[8]脲和桥联双吡啶衍生物构筑了两种超分子环结构,并且通过加入酸使该结构转变为准轮烷,进一步加入碱可以使超分子环状结构恢复。该研究的创新之处在于通过酸碱调控主客体的作用从而实现了线状客体分子在环状和线状构象之间的可逆调控。
5.合成了一个受体-给体-受体型的线状分子,研究了其与葫芦[8]脲的组装行为。客体分子同一倍量葫芦[8]脲可以形成[2]准轮烷,进一步加入葫芦[8]脲可以连接两个[2]准轮烷形成[5]准轮烷,加入酸之后会使得[5]准轮烷分离而形成[3]准轮烷,再加入碱可以使得[5]准轮烷恢复。该研究的创新之处在于通过酸碱调控主客体间的作用从而实现非共价粘贴和断开轴分子,从而实现了准轮烷组装模式的可控转换。
As an important and intriguing area in supramolecular chemistry, the construction of rotaxanes and pseudorotaxanes based on the macrocyclic hosts and the relative guests has attracted more and more attentions. The investigations on their structures and functions not only help us to understand the non-covalent bonds, but also promote the development of molecular machinery and nanoscience. Herein, we have designed and constructed some novel pseudorotaxanes and rotaxanes, based on the unique complexation behaviors of macrocyclic hosts, including crown ethers and cucurbiturils and the relative guests. Furthermore, their switchable self-assembly behaviors under specific external stimuli have also been investigated. The details are as follows:
1. The general aspect of supramolecular chemistry was discussed briefly. Some representative results on rotaxanes and pseudorotaxanes based on crown ethers and cucurbiturils were reviewed.
2. Two pseudorotaxanes could be combined to form a twin-axial hetero[7]rotaxane by using the copper-catalyzed alkyne-azide "click" reaction. The synthetic route, in which twin-axial and single-axial rotaxanes are formed simultaneously, combines self-assembly and the formation of covalent bonds to ensure the correct positioning of the two types of rings in the final product. This strategy allows precise positional control in the final [n]rotaxane product and will thus be beneficial for the construction of more complicated interlocked molecules with well-defined structures and functions.
3. A series of styryl pyridinium and4,4'-bipyridinium derivatives were synthesized. The self-assembly behaviors between some of these organic cationic guests and cucurbit[7,8]urils and a-cyclodextrin were investigated.
4. Two stable supramolecular loops were successfully constructed by the molecular recognition of cucurbit[8]uril (CB[8]) and the homoditopic bispyridinium derivatives. The interconversion between molecular loops and [2]pseudorotaxanes could be reversibly switched under neutral and acidic condition, while the CB[8] moved between the bispyridinium unit and the linker. The result provides a noncovalent and reversible way to efficiently control the molecular conformations by noncovalent interactions.
5. An acceptor-donor-acceptor type linear molecule containing one electron-rich naphthoxy unit and two mono-charged viologen units was synthesized. Through the noncovalent interaction of equimolar CB[8] with the linear guest molecule, we firstly obtained a [2]pseudorotaxane, then added excessive CB[8] to form a [5]pseudorotaxane. Its transformation to [3]pseudorotaxane was achieved through detaching the two axle molecules in the presence of acid, which could be reversed by the addition of base. The result provides an unexplored approach for elongating reversibly the linear molecules by noncovalent interactions.
1.首先简要介绍了超分子化学的研究概况,对基于冠醚和葫芦脲构筑的轮烷和准轮烷体系所取得的最新成果进行了综述。
2.基于冠醚/二级胺主客体作用构筑了两种含有炔和叠氮基团的准轮烷,进而通过click反应将其共价连接合成了一种双轴杂[7]轮烷。在该轮烷中外侧的苯环可以封端21冠7环组分,又可以继续封端中心的34冠10环组分。该研究的创新之处在于这种以稳定的超分子配合物作为反应模块的策略,不仅简化了传统的穿线封端方法复杂的合成步骤,而且可以精确控制轮烷结构中两种环状组分的位置。该研究为有机超分子化学的发展提供了一种模块化的构筑策略,可用于构筑具有独特结构和功能的复杂机械互锁分子。
3.合成了一系列含有不同修饰基团的苯乙烯吡啶和联吡啶衍生物,并研究了这两类有机阳离子客体与葫芦[7]脲、葫芦[8]脲以及α-环糊精等大环主体的组装行为。
4.通过葫芦[8]脲和桥联双吡啶衍生物构筑了两种超分子环结构,并且通过加入酸使该结构转变为准轮烷,进一步加入碱可以使超分子环状结构恢复。该研究的创新之处在于通过酸碱调控主客体的作用从而实现了线状客体分子在环状和线状构象之间的可逆调控。
5.合成了一个受体-给体-受体型的线状分子,研究了其与葫芦[8]脲的组装行为。客体分子同一倍量葫芦[8]脲可以形成[2]准轮烷,进一步加入葫芦[8]脲可以连接两个[2]准轮烷形成[5]准轮烷,加入酸之后会使得[5]准轮烷分离而形成[3]准轮烷,再加入碱可以使得[5]准轮烷恢复。该研究的创新之处在于通过酸碱调控主客体间的作用从而实现非共价粘贴和断开轴分子,从而实现了准轮烷组装模式的可控转换。
As an important and intriguing area in supramolecular chemistry, the construction of rotaxanes and pseudorotaxanes based on the macrocyclic hosts and the relative guests has attracted more and more attentions. The investigations on their structures and functions not only help us to understand the non-covalent bonds, but also promote the development of molecular machinery and nanoscience. Herein, we have designed and constructed some novel pseudorotaxanes and rotaxanes, based on the unique complexation behaviors of macrocyclic hosts, including crown ethers and cucurbiturils and the relative guests. Furthermore, their switchable self-assembly behaviors under specific external stimuli have also been investigated. The details are as follows:
1. The general aspect of supramolecular chemistry was discussed briefly. Some representative results on rotaxanes and pseudorotaxanes based on crown ethers and cucurbiturils were reviewed.
2. Two pseudorotaxanes could be combined to form a twin-axial hetero[7]rotaxane by using the copper-catalyzed alkyne-azide "click" reaction. The synthetic route, in which twin-axial and single-axial rotaxanes are formed simultaneously, combines self-assembly and the formation of covalent bonds to ensure the correct positioning of the two types of rings in the final product. This strategy allows precise positional control in the final [n]rotaxane product and will thus be beneficial for the construction of more complicated interlocked molecules with well-defined structures and functions.
3. A series of styryl pyridinium and4,4'-bipyridinium derivatives were synthesized. The self-assembly behaviors between some of these organic cationic guests and cucurbit[7,8]urils and a-cyclodextrin were investigated.
4. Two stable supramolecular loops were successfully constructed by the molecular recognition of cucurbit[8]uril (CB[8]) and the homoditopic bispyridinium derivatives. The interconversion between molecular loops and [2]pseudorotaxanes could be reversibly switched under neutral and acidic condition, while the CB[8] moved between the bispyridinium unit and the linker. The result provides a noncovalent and reversible way to efficiently control the molecular conformations by noncovalent interactions.
5. An acceptor-donor-acceptor type linear molecule containing one electron-rich naphthoxy unit and two mono-charged viologen units was synthesized. Through the noncovalent interaction of equimolar CB[8] with the linear guest molecule, we firstly obtained a [2]pseudorotaxane, then added excessive CB[8] to form a [5]pseudorotaxane. Its transformation to [3]pseudorotaxane was achieved through detaching the two axle molecules in the presence of acid, which could be reversed by the addition of base. The result provides an unexplored approach for elongating reversibly the linear molecules by noncovalent interactions.
引文
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