Supramolecular Assemblies Based on Intramolecular Three-Center Hydrogen Bond and their Applications

doi:10.6023/cjoc202005053

Abstract

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

Cite this article

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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Fig. & Tab. 33

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

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

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

Figure 4. Aromatic oligoamide foldamers with different internal diameters

Figure 5. Structures of aromatic oligoamide foldamers24~26

Figure 6. Structures of aromatic oligohydrazide foldamers27 and28

Figure 7. Structures of compounds29~31

Figure 8. Structures of compounds32~35

Figure 9. Structures of compounds36 and37

Figure 10. Structures of quinoline amide oligomers38a~38e

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

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

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

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

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

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

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

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

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

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

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

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

. Asymmetric hydrogenation catalysted by76[Rh]

Figure 21. Structures of pentameric arylamide macrocycles77~79

Figure 22. Structures of hexameric arylamide macrocycles80 and81

Figure 23. Molecular structures of aromatic oligoamide foldamers82~84

Figure 24. Structures of macrocycles85 and86

Figure 25. Structures of compounds87~90

Figure 26. Structures of compounds91 and92

Figure 27. Structures of compounds93 and94

Figure 28. Structures of compounds95

Figure 29. Structures of macrocycles96

Figure 30. Structures of macrocycles97

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