基于分子内三中心氢键的超分子组装体系及其应用

doi:10.6023/cjoc202005053

摘要/Abstract

分子内三中心氢键被视为是一种高效且可靠地控制分子构象的手段, 可以诱导线性分子形成特定构象(折叠、螺旋、扩展及“之”字形等). 根据氢键结合原子的种类, 系统地综述了基于O…H…O型、S…H…X (X=N, O)型、N…H…X (X=N, O)型、F…H…X (X=F, O, N)型分子内三中心氢键的超分子组装体系的研究进展, 重点介绍了大环化合物、折叠体与含孔螺旋化合物、分子拉链等超分子组装体的合成以及它们在促进有机反应、分子识别、跨膜通道、分子机器、软物质材料等领域的应用. 希望为此类超分子组装体的合成及应用提供有益参考.

关键词: 分子内三中心氢键, 超分子自组装, 结构设计, 构象控制, 应用

The intramolecular three-center hydrogen bond is regarded as an efficient and reliable means to control molecular conformation, which can induce linear molecules to form specific conformations (folding, helix, expansion, zigzag, etc.). In this paper, the research progress on supramolecular assemblies based on different types of intramolecular three-center hydrogen bond is summarized in detail according to the kinds of hydrogen bonding atoms, such as O…H…O, S…H…X (X=N, O), N…H…X (X=N, O), F…H…X (X=F, O, N), and so on. More specifically, the synthesis of supramolecular assemblies is elaborated, including macrocyclic compounds, foldamers, porous helical compounds and molecular duplexes. Furthermore, their applications in promoting organic reactions, molecular recognition, transmembrane channels, molecular machines, soft materials are introduced. It is anticipated that this review can provide a useful reference for the synthesis and applications of the three-center hydrogel bond-based supramolecular assemblies.

Key words: intramolecular three-center hydrogen bond, supramolecular self-assembly, structure design, conformation control, application

引用此文

裴强, 丁爱祥, 吴晋晋. 基于分子内三中心氢键的超分子组装体系及其应用[J]. 有机化学, 2021, 41(1): 105-125.

Qiang Pei, Aixiang Ding, Jinjin Wu. Supramolecular Assemblies Based on Intramolecular Three-Center Hydrogen Bond and their Applications[J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 105-125.

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图/表 33

图1. 氢键结合方式: 两中心氢键(1), 三中心氢键(2和3)和四中心氢键(4)

Figure 1. Bonding patterns of hydrogen bond: two-center hydrogen bond (1), three-center hydrogen bond (2 and3), and four-center hydrogen bond (4)

图2. (a)分子内三中心氢键酰胺5及其异构体5a~5c的结构, 以及(b)分子内两中心氢键酰胺6和7的结构

Figure 2. (a) Structures of amide5 bearing intramolecular three- center hydrogen bond and it’s isomers5a~5c, and (b) structures of intramolecular two-center hydrogen bonded amides6 and7

图3. 不同类型的分子内三中心氢键

Figure 3. Different types of intramolecular three-center hydrogen bonds

图4. 具有不同孔径的芳香低聚酰胺折叠体

Figure 4. Aromatic oligoamide foldamers with different internal diameters

图5. 芳香低聚酰胺折叠体24~26的结构

Figure 5. Structures of aromatic oligoamide foldamers24~26

图6. 低聚芳香酰肼折叠体27和28的结构

Figure 6. Structures of aromatic oligohydrazide foldamers27 and28

图7. 化合物29~31的结构

Figure 7. Structures of compounds29~31

图8. 化合物32~35的结构

Figure 8. Structures of compounds32~35

图9. 化合物36和37的结构

Figure 9. Structures of compounds36 and37

图10. 喹啉酰胺低聚物38a~38e的结构

Figure 10. Structures of quinoline amide oligomers38a~38e

图11. 基于F…H…F型分子内三中心氢键的低聚芳香酰胺折叠体

Figure 11. Aromatic oligoamide foldamers induced by the F…H…F type intramolecular three-center hydrogen bond

图12. 基于C—H形成的F…H…F型分子内三中心氢键的折叠体

Figure 12. Foldamers based on the F…H…F type intramolecular three-center hydrogen bond formed by C—H

图13. 六聚芳酰胺大环43和五聚芳酰胺大环44的结构

Figure 13. Structures of hexameric arylamide macrocycles43 and pentameric arylamide macrocycles44

图14. (a)芳香低聚酰肼大环(45和46)、(b)四聚芳香磺酰胺大环(47和48)、(c)五聚吡啶酮酰胺大环(49)

Figure 14. (a) Aromatic oligohydrazide macrocycles (45 and46), (b) tetrameric aromatic sulfonamide macrocycles (47 and48), and (c) pentameric pyridone amide macrocycles (49)

图15. 基于N…H…X (X=N, O)型分子内三中心氢键的大环

Figure 15. Macrocycles based on the N…H…X (X=N, O) typed intramolecular three-center hydrogen bond

图16. 基于C—H形成的N…H…N型分子内三中心氢键的大环

Figure 16. Macrocycle based on the N…H…N typed intramolecular three-center hydrogen bond formed by C—H

图17. F…H…X (X=F, N)型分子内三中心氢键诱导形成的大环

Figure 17. Macrocycles induced by the F…H…X (X=F, N) typed intramolecular three-center hydrogen bond

图18. 分子内三中心氢键诱导形成的拓展结构

Figure 18. Extended structures induced by intramolecular three-center hydrogen bond

图19. 基于S…H…X (X=N、O)型分子内三中心氢键的拓展结构

Figure 19. Extended structure induced by S…H…X (X=N, O) type intramolecular three-center hydrogen bond

图20. 基于分子内三中心氢键的分子拉链

Figure 20. Molecular duplexes based on intramolecular three- center hydrogen bond

图式1. 分子内三中心氢键预组织作用促进缩合反应

Scheme 1. Condensation reaction promoted by the preorganization of intramolecular three-center hydrogen bond

图式2. 分子内三中心氢键预组织作用促进有机反应: (a)氧化反应, (b)水解反应

Scheme 2. Reactions promoted by the preorganization of intramolecular three-center hydrogen bond: (a) oxidation reaction, (b) hydrolysis reaction

Scheme 3. 手性催化剂76[Rh]催化的不对称氢化反应

. Asymmetric hydrogenation catalysted by76[Rh]

图21. 五聚芳酰胺大环77~79的结构

Figure 21. Structures of pentameric arylamide macrocycles77~79

图22. 六聚芳酰胺大环80和81的结构

Figure 22. Structures of hexameric arylamide macrocycles80 and81

图23. 寡聚芳酰胺折叠体82~84的分子结构

Figure 23. Molecular structures of aromatic oligoamide foldamers82~84

图24. 大环化合物85和86的结构

Figure 24. Structures of macrocycles85 and86

图25. 化合物87~90的结构

Figure 25. Structures of compounds87~90

图26. 化合物91和92的结构

Figure 26. Structures of compounds91 and92

图27. 化合物93和94的结构

Figure 27. Structures of compounds93 and94

图28. 化合物95的结构

Figure 28. Structures of compounds95

图29. 大环化合物96的结构

Figure 29. Structures of macrocycles96

图30. 大环化合物97的结构

Figure 30. Structures of macrocycles97

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