手性亚胺有机分子笼的合成及应用研究

doi:10.6023/cjoc202401011

有机化学 ›› 2024, Vol. 44 ›› Issue (9): 2617-2639.DOI: 10.6023/cjoc202401011 上一篇下一篇

综述与进展

手性亚胺有机分子笼的合成及应用研究

陈璐怡^a, 谭梦霞^a, 金迦南^a, 张子彬^a, 黄飞鹤^b^,^c, 李世军^a^,^*(), 李云霞^a^,^*()

a 杭州师范大学材料与化学化工学院有机硅化学及材料技术教育部重点实验室杭州 311121
b 浙江大学化学系司徒塔特分子科学研究院杭州 310058
c 浙江大学杭州国际科创中心浙江-以色列自组装功能材料联合实验室杭州 311215

收稿日期:2024-01-12 修回日期:2024-03-18 发布日期:2024-04-10
通讯作者: 李世军, 李云霞
基金资助:
国家自然科学基金(21773052); 国家自然科学基金(22071040); 浙江省自然科学基金(LZ24B020005)

Synthesis and Application of Chiral Organic Imine Molecular Cages

Luyi Chen^a, Mengxia Tan^a, Jia'nan Jin^a, Zibin Zhang^a, Feihe Huang^b^,^c, Shijun Li^a(), Yunxia Li^a()

a College of Material, Chemistry and Chemical Engineering, Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou 311121
b Stoddart Institute of Molecular Science, Department of Chemistry, Zhejiang University, Hangzhou 310058
c Zhejiang-Israel Joint Laboratory of Self-Assembling Functional Materials, ZJU-Hangzhou Global Scientific and Technological Innovation Center, Zhejiang University, Hangzhou 311215

Received:2024-01-12 Revised:2024-03-18 Published:2024-04-10
Contact: Shijun Li, Yunxia Li
Supported by:
National Natural Science Foundation of China(21773052); National Natural Science Foundation of China(22071040); Natural Science Foundation of Zhejiang Province(LZ24B020005)

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摘要/Abstract

作为一类新型多孔材料, 多孔有机分子笼(POCs)在分子识别、气体存储与分离、催化及传感等方面表现出优异的性能. 此外, POCs的良好溶解性赋予其易于加工处理的优势, 使其可与其它材料复合获得更多结构与性能. 作为POCs主要家族成员之一, 基于动态亚胺键的亚胺有机分子笼的研究近年取得巨大进展, 其中手性亚胺有机分子笼展现了POCs在手性识别、对映选择性分离及不对称催化等领域的广阔应用前景. 系统综述了手性亚胺有机分子笼的合成及其应用等方面的研究进展, 归纳总结了手性亚胺有机分子笼的三种有效合成策略, 包括利用手性构筑基元直接合成、利用非手性构筑基元在对称性破缺效应下的手性组装和利用外消旋构筑基元的手性自分类组装. 并回顾了近年来手性亚胺有机分子笼在手性识别、手性色谱分离及不对称催化领域的应用.

关键词: 多孔有机分子笼, 手性, 亚胺, 合成策略, 自组装

As a kind of novel porous materials, porous organic molecular cages (POCs) exhibit excellent properties in the field of molecular recognition, gas storage and separation, catalysis and sensing. Moreover, their good solubilities make them easily fabricate composite materials to obtain more complicated structures and interesting performances. As one of main family members of POCs, organic imine molecular cages based on dynamic imine bonds have been extensively studied. Among them, chiral organic imine molecular cages have exhibited the wide applications of POCs in the fields such as chiral recognition, enantiomer separation, asymmetric catalysis, and so on. In order to provide a comprehensive overview of the synthesis and applications of chiral organic imine molecular cages, three effective synthetic strategies of chiral organic imine molecular cages, including direct synthesis by using enantiopure chiral building blocks, chiral assembly with achiral building blocks under the effect of symmetry breaking, and chiral self-sorting assembly with racemic building blocks, are summarized. The recent progresses of the applications of chiral organic molecular imine cages in the fields of chiral molecular recognition, chiral chromatographic separation and asymmetric catalysis are also briefly retrospected.

Key words: porous organic molecular cage, chirality, imine, synthetic strategy, self-assembly

引用此文

陈璐怡, 谭梦霞, 金迦南, 张子彬, 黄飞鹤, 李世军, 李云霞. 手性亚胺有机分子笼的合成及应用研究[J]. 有机化学, 2024, 44(9): 2617-2639.

Luyi Chen, Mengxia Tan, Jia'nan Jin, Zibin Zhang, Feihe Huang, Shijun Li, Yunxia Li. Synthesis and Application of Chiral Organic Imine Molecular Cages[J]. Chinese Journal of Organic Chemistry, 2024, 44(9): 2617-2639.

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图/表 32

图式1. 亚胺笼CC1、CC2、CC3-R和CC4-S的合成

Scheme 1. Synthesis of imine cages CC1, CC2, CC3-R and CC4-S

图式2. 手性亚胺笼CC5~CC10的合成

Scheme 2. Synthesis of chiral imine cages CC5~CC10

图式3. 手性亚胺笼CC11-R、CC12-R、CC13-R和CC14-S的合成

Scheme 3. Synthesis of chiral imine cages CC11-R, CC12-R, CC13-R and CC14-S

图式4. 手性亚胺笼CC15和CC16的合成

Scheme 4. Synthesis of chiral imine cage CC15 and CC16

图式5. 手性磷酸亚胺笼CC17的合成

Scheme 5. Synthesis of chiral phosphate imine cage CC17

图1. (a) 线性四醛前驱体18~20的化学结构及(b)手性亚胺笼CC18~CC20 (R笼)单晶X射线结构的侧视图和透过笼窗的视图(省略了氢原子和溶剂分子)

Figure 1. (a) Chemical structure of linear tetraaldehyde precursors 18~20 and (b) side view and view through the cage windows of CC18~CC20 obtained from single-crystal X-ray structures (R cage enantiomers are shown) (Hydrogen atoms and solvent molecules are removed for clarity)

图式6. 手性亚胺笼CC21和CC22的合成

Scheme 6. Synthesis of chiral imine cages CC21 and CC22

图式7. (a)手性亚胺笼CC23~CC26的溶液相合成以及(b)亚胺笼CC23-S、CC24-R、CC25-R和CC26-R的化学结构

Scheme 7. (a) Solution-phase synthesis of chiral imine cages CC23~CC26, and (b) chemical structures of the four cages CC23-S, CC24-R, CC25-R and CC26-R

图式8. 同手性亚胺笼(S)-CC273＋和(R)-CC273＋的合成

Scheme 8. Synthesis of homochiral imine cages (S)-CC273＋ and (R)-CC273＋

图式9. 同手性亚胺笼CC28-R和CC28-S的合成

Scheme 9. Synthesis of homochiral imine cages CC28-R and CC28-S

图式10. 同手性亚胺笼CC29和CC30的合成

Scheme 10. Synthesis of homochiral imine cages CC29 and CC30

图式11. 手性亚胺笼CC31和CC32的合成和结构(省略了氢原子)

Scheme 11. Synthesis and structure of chiral imine cages CC31 and CC32 (Hydrogen atoms are omitted for clarity)

图式12. 螺手性亚胺笼M,M,M-CC33和P,P,P-CC33的合成

Scheme 12. Synthesis of helically chiral imine cages M,M,M-CC33 and P,P,P-CC33

图式13. 轴手性亚胺笼(R)/(S)-CC34和胺笼(R)/(S)-CC34R的合成

Scheme 13. Synthesis of axially chiral imine cages (R)/(S)-CC34, and the amine cages (R)/(S)-CC34R

图式14. 异手性亚胺笼(S,R)-CC35和(R,S)-CC35的合成

Scheme 14. Synthesis of heterochiral imine cages (S,R)-CC35 and (R,S)-CC35

图式15. 面旋转手性亚胺笼CC36和CC37的合成

Scheme 15. Synthesis of chiral face-rotating imine cages CC36 and CC37

图2. 二维手性面构筑基元组装为三维手性多面体笼

Figure 2. 3D chiral polyhedral cages originated from 2D chiral facial units

图3. (a)面旋转手性亚胺笼CC38和CC39的合成以及(b) TPE单元面P或M螺旋构型的面同向多面体笼(6M)-/(6P)-CC38和面异向多面体笼(2P4M)-/(4P2M)-CC39的卡通图

Figure 3. (a) Synthesis of chiral face-rotating imine cages CC38 and CC39, and (b) cartoons to show the TPE con?gurations in the homodirectional cubes (6P)-CC38 and (6M)-CC38, and the heterodirectional cubes (4P2M)-CC39 and (2P4M)-CC39

图式16. 面旋转手性亚胺笼CC40和CC41的合成

Scheme 16. Synthesis of chiral face-rotating imine cages CC40 and CC41

图式17. 手性亚胺笼CC42~CC44的合成

Scheme 17. Synthesis of chiral imine cages CC42~CC44

图式18. 同手性亚胺笼CC45和异手性亚胺笼CC46的合成

Scheme 18. Synthesis of homochiral imine cages CC45 and heterochiral imine cage CC46

图式19. 同手性亚胺笼(P)-CC47, (M)-CC47和异手性亚胺笼(P,M)-CC48的合成

Scheme 19. Synthesis of homochiral imine cages (P)-CC47, (M)-CC47 and heterochiral imine cage (P,M)-CC48

图式20. 同手性亚胺笼CC49的合成(省略了丁基基团)

Scheme 20. Synthesis of homochiral imine cages CC49 (butyl groups are omitted for clarity)

图式21. 同手性自由基亚胺笼CC50及其前驱体49的合成

Scheme 21. Synthesis of homochiral radical imine cages CC50 and its precursor 49

Entry	Host	ee/%
1	M,M,M-CC33	60 (S)
2	P,P,P-CC33	58 (R)
3	M,M,M-CC33	84 (S)
4	P,P,P-CC33	67 (R)
5	M,M,M-CC33	23 (S)
6	P,P,P-CC33	20 (R)
7	34	1 (S)
8	34	2 (R)

表1. 手性吸附实验数据

Table 1. Data of chiral adsorption experiments

CSP	Types of chiral substances separated	Ref.
CC3-R	Chiral alcohols, diols, amines, alcohol amines, esters, ketones, ethers, halohydrocarbons, organic acids, amino acid methyl esters, sulfoxides and linear alkanes	[55, 56]
CC5	Chiral alcohols, esters, ethers and epoxides	[57]
CC6	Chiral alcohols, esters, ketones, ethers, halohydrocarbons, epoxides, and organic acids	[58]
CC8	Chiral alcohols, esters, ethers, and epoxides	[59]
CC11-R	Derivatized amino acids, alcohols, alcohol amines, esters, ethers, ketones, and epoxides	[60]

表2. 手性亚胺笼作固定相制备的GC色谱柱所分离各种类型的手性物质

Table 2. Types of chiral substances on the chiral imine cage-coated GC capillary column

图式22. 同手性亚胺笼CC3-R/-S和CC51-R的绿色合成

Scheme 22. Green synthesis of homochiral imine cages CC3-R, CC3-S and CC51-R

Analyte	Resolution					Separation factor
Analyte	CC3-R^a	CC3-S^b	CC51-R^c	225^d	B^e	CC3-R^a	CC3-S^b	CC51-R^c	225^d	B^e
Butan-2-ol	1.53	1.52	1.73	1.55	—	1.9	1.9	1.6	1.1	1.0
3-Butyn-2-ol	1.49	1.46	2.67	2.14	0.42	1.5	1.4	1.6	1.1	1.1
4-Heptyn-2-ol	—	—	1.82	—	—	1.0	1.0	1.4	1.0	1.0
Nonan-3-ol	—	—	1.51	—	—	1.0	1.2	1.4	1.0	1.0
5-Hexyn-3-ol	0.81	0.76	1.47	—	—	1.4	1.4	1.2	1.0	1.0
4-Penten-2-ol	0.65	0.57	1.56	—	—	1.3	1.2	1.3	1.0	1.0

表3. 在CC3-R、CC3-S、CC51-R、Cyclosil-B和β-DEX 225色谱柱上分离部分手性醇的分离度和分离因子

Table 3. Resolution and separation factor for the separation of selected chiral alcohols on CC3-R, CC3-S, CC51-R, Cyclosil-B and β-DEX 225

图4. 基于手性亚胺笼CC23-R的手性固定相CSP-1和CSP-2

Figure 4. CSPs CSP-1 and CSP-2 based on CC23-R

Entry	Catalyst	Time/d	Yield/%	anti/syn	ee/%
1	CC31^a	1	98	88∶12	83
2	CC32^a	2	99	93∶7	92
3	BPP	4	96	89∶11	88
4	L-Proline	10	80	45∶45	77
5	CC31^b	1	97	88∶12	－83
6	CC32^b	2	98	93∶7	－91

表4. 手性亚胺笼和相关催化剂催化的不对称Aldol反应

Table 4. Asymmetric aldol reactions catalyzed by chiral imine cages and related catalysts

图式23. 手性亚胺笼CC52、CC53和胺笼CC52R、CC53R的合成

Scheme 23. Synthesis of chiral imine cages CC52, CC53 and amine cages CC52R, CC53R

图式24. CC52R-Ni和CC53R-Ni催化的不对称Michael加成

Scheme 24. Asymmetric Michael additions catalyzed by CC52R-Ni and CC53R-Ni

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手性亚胺有机分子笼的合成及应用研究

Synthesis and Application of Chiral Organic Imine Molecular Cages

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