晶体生长中基于CH…O弱氢键导向堆积的二级结构的设计与合成
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摘要
分子聚集体多级结构的理性设计与构筑是当前化学研究的重要前沿方向与难题，如何精确设计并利用分子间的弱相互作用力来获得特定的具有高级结构的分子组装体系是极富挑战性的研究课题，主要因为晶体在生长过程中分子结构的多样性会导致分子堆积形态的多样性，从而使人们还无法根据单个分子结构来准确预测它在晶体结构中的堆积形态。显然在自组装形成的分级结构中，如果一系列拥有多样性取代基的组装子在自组装过程中出现具有重复性的组装区域结构，表达出可预测性的基元组装模式，那么我们在导向合成预期结构的分子堆积体时就有规律可循，也为高级堆积结构的理性设计与合成建立理论指导提供基础。
本论文系统综述了近些年来固相中CH…O弱氢键的研究状况。我们以甘脲构筑的一系列拥有多样性取代基的分子夹为研究对象，开展了以CH…O弱氢键为主要驱动力导向堆积的二级结构的研究，主要内容如下：
以酯基甘脲为基本模块，设计合成了13个不同芳环取代基团(H，OMe，NO_2，Me，Br)的对称及不对称的分子夹，并得到了其中12个化合物的晶体结构。首次得到了一个结构多样性，而二级结构的堆积态一致性的组装体系，即1，4-位的甲氧基芳环选择性的堆积在一起的基元组装模式，这为高级结构的理性设计与合成提供了很大的启发和借鉴意义。
此外，为了考察基于不同取代基甘脲构筑的分子夹在晶体生长过程中高级结构形成的规律，我们设计合成了11种甘脲化合物并根据这些甘脲化合物合成了9个不同取代基甘脲的分子夹，得到5个化合物的晶体结构。晶体结构分析显示取代基团的多样性导致了组装结构的多样性。如化合物Ⅲ-2a(R=H)可以得到高级结构，而当H原子被其它基团取代后，破坏了这种组装形式，没有高级结构形成。同时我们还讨论了同质多晶体中溶剂在晶体堆积中的作用。
另外，新颖人工受体的合成也是超分子化学研究的热点之一，我们还以廉价易得的苯基甘脲为构筑板块，首次采用一锅合成法就能够得到重要的中间体化合物IV-1，这个方法的优点是温和的反应条件，产物单一，较高的收率和不需要分离中间体。我们还进行了立体大环化合物的合成探索，为获得一类新型的人工受体合成方法提供了实验基础。同时我们还获得了6个苯基甘脲分子夹化合物的晶体结构，探讨了晶体生长过程中高级结构形成的规律。尤其值得注意的是在对映异构体Ⅳ-(±)8和Ⅳ-(±)11的晶体结构中，都可以得到中心对称的消旋的二聚体组装模式，这也是一种由CH...O弱氢键为主要驱动力导向的选择性的组装模式。
The rational design and construction of molecular aggregates possessing multi-level structure is an important frontier research in chemistry. And how to accurately design and utilize intermolecular weak interaction forces to obtain particular molecular assemble system with high-level structures is a research item full of challenge, because the diversity of molecular structure could cause multiple molecular stacking models during the course of crystal growth. So it is difficult to predict molecular stacking model based on a single molecular structure. Obviously, if a series of assemble units with multiple substituted groups show the same assemble area in the self-assemble course, and conveys anticipated base assemble model, we can use it to synthesize molecular aggregation with anticipated stacking models, which provides a foundation of building theory and guidance for high-level structure's rational design and synthesis.
In this thesis, the research works on weak CH...O hydrogen bond in solid phase was systematically reviewed. We used a series of molecular clips based on glycoluril having various substituted groups as research objects, and studied the rule of formation of secondary structure using weak CH...O hydrogen bond as main driven forces. The research results were summarized below:
Thirteen symmetrical and asymmetrical molecular clips based on diethoxycarbonyl glycoluril with different substituted groups of aromatic rings (H, OMe, NO_2, Me, Br) were designed and synthesized, and crystal structures of twelve compounds were obtained. We firstly attained a system that various structures can assemble the same secondary structure using weak CH...O hydrogen bond as main driven forces, in which p-dimethoxy-o-xylylene rings are in the interior of the dimeric molecular clips. Then it will provide much great enlightenment and reference meaning for the rational design and synthesis of more high-level structures.
Furthermore, in order to investigate the high-level structure formation rule of molecular clips constructed by glycoluril with different substituted groups during crystal growth, eleven kinds of glycoluril compounds and nine molecular clips based on these glycoluril compounds were synthesized, and crystal structure of five molecular clips were also obtained. After analysis of these crystal structures, it can conclude that various structure of substituted group can cause variety of stacking models. Such as high-level structure of compound III-2a (R = H) can be obtained, but this high-level structure will disappear when H atom is displaced by other groups, these substituted groups destroyed this assemble model. We also described the function of solvent molecule in polymorphs about crystal packing.
Besides, synthesis of novel artificial acceptors is also a hotspot of supramolecular chemistry. The major intermediate compound FV-1 was synthesized firstly using one-pot method with cheap diphenylglycoluril as building block. The advantage of this method is mild condition, single product formation, good yield, and no need for separating intermediates. Meantime, synthesis exploration of steric macrocyclic compound was also proceeded, which provided experiment foundation for gaining synthesis method of a novel kind of artificial acceptor. And 6 crystal structure of molecular clips based on diphenylglycoluril were also obtained, and formation rule of high-level structure during crystal growth was conferred. It is especially taking care that the assemble model of racemic dimmers with center symmetry can be obtained in crystal structure of enantiomers IV-(±)8 and IV-(±)11, which is also a kind of selective assemble model driven by weak CH... O hydrogen bond.
本论文系统综述了近些年来固相中CH…O弱氢键的研究状况。我们以甘脲构筑的一系列拥有多样性取代基的分子夹为研究对象，开展了以CH…O弱氢键为主要驱动力导向堆积的二级结构的研究，主要内容如下：
以酯基甘脲为基本模块，设计合成了13个不同芳环取代基团(H，OMe，NO_2，Me，Br)的对称及不对称的分子夹，并得到了其中12个化合物的晶体结构。首次得到了一个结构多样性，而二级结构的堆积态一致性的组装体系，即1，4-位的甲氧基芳环选择性的堆积在一起的基元组装模式，这为高级结构的理性设计与合成提供了很大的启发和借鉴意义。
此外，为了考察基于不同取代基甘脲构筑的分子夹在晶体生长过程中高级结构形成的规律，我们设计合成了11种甘脲化合物并根据这些甘脲化合物合成了9个不同取代基甘脲的分子夹，得到5个化合物的晶体结构。晶体结构分析显示取代基团的多样性导致了组装结构的多样性。如化合物Ⅲ-2a(R=H)可以得到高级结构，而当H原子被其它基团取代后，破坏了这种组装形式，没有高级结构形成。同时我们还讨论了同质多晶体中溶剂在晶体堆积中的作用。
另外，新颖人工受体的合成也是超分子化学研究的热点之一，我们还以廉价易得的苯基甘脲为构筑板块，首次采用一锅合成法就能够得到重要的中间体化合物IV-1，这个方法的优点是温和的反应条件，产物单一，较高的收率和不需要分离中间体。我们还进行了立体大环化合物的合成探索，为获得一类新型的人工受体合成方法提供了实验基础。同时我们还获得了6个苯基甘脲分子夹化合物的晶体结构，探讨了晶体生长过程中高级结构形成的规律。尤其值得注意的是在对映异构体Ⅳ-(±)8和Ⅳ-(±)11的晶体结构中，都可以得到中心对称的消旋的二聚体组装模式，这也是一种由CH...O弱氢键为主要驱动力导向的选择性的组装模式。
The rational design and construction of molecular aggregates possessing multi-level structure is an important frontier research in chemistry. And how to accurately design and utilize intermolecular weak interaction forces to obtain particular molecular assemble system with high-level structures is a research item full of challenge, because the diversity of molecular structure could cause multiple molecular stacking models during the course of crystal growth. So it is difficult to predict molecular stacking model based on a single molecular structure. Obviously, if a series of assemble units with multiple substituted groups show the same assemble area in the self-assemble course, and conveys anticipated base assemble model, we can use it to synthesize molecular aggregation with anticipated stacking models, which provides a foundation of building theory and guidance for high-level structure's rational design and synthesis.
In this thesis, the research works on weak CH...O hydrogen bond in solid phase was systematically reviewed. We used a series of molecular clips based on glycoluril having various substituted groups as research objects, and studied the rule of formation of secondary structure using weak CH...O hydrogen bond as main driven forces. The research results were summarized below:
Thirteen symmetrical and asymmetrical molecular clips based on diethoxycarbonyl glycoluril with different substituted groups of aromatic rings (H, OMe, NO_2, Me, Br) were designed and synthesized, and crystal structures of twelve compounds were obtained. We firstly attained a system that various structures can assemble the same secondary structure using weak CH...O hydrogen bond as main driven forces, in which p-dimethoxy-o-xylylene rings are in the interior of the dimeric molecular clips. Then it will provide much great enlightenment and reference meaning for the rational design and synthesis of more high-level structures.
Furthermore, in order to investigate the high-level structure formation rule of molecular clips constructed by glycoluril with different substituted groups during crystal growth, eleven kinds of glycoluril compounds and nine molecular clips based on these glycoluril compounds were synthesized, and crystal structure of five molecular clips were also obtained. After analysis of these crystal structures, it can conclude that various structure of substituted group can cause variety of stacking models. Such as high-level structure of compound III-2a (R = H) can be obtained, but this high-level structure will disappear when H atom is displaced by other groups, these substituted groups destroyed this assemble model. We also described the function of solvent molecule in polymorphs about crystal packing.
Besides, synthesis of novel artificial acceptors is also a hotspot of supramolecular chemistry. The major intermediate compound FV-1 was synthesized firstly using one-pot method with cheap diphenylglycoluril as building block. The advantage of this method is mild condition, single product formation, good yield, and no need for separating intermediates. Meantime, synthesis exploration of steric macrocyclic compound was also proceeded, which provided experiment foundation for gaining synthesis method of a novel kind of artificial acceptor. And 6 crystal structure of molecular clips based on diphenylglycoluril were also obtained, and formation rule of high-level structure during crystal growth was conferred. It is especially taking care that the assemble model of racemic dimmers with center symmetry can be obtained in crystal structure of enantiomers IV-(±)8 and IV-(±)11, which is also a kind of selective assemble model driven by weak CH... O hydrogen bond.
引文
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