阴离子-π相互作用研究进展

doi:10.6023/cjoc202308003

摘要/Abstract

阴离子-π相互作用是主客体化学中的一种非共价引力相互作用. 通常, 芳香族π-系统被认为是富电子的, 可能与负电荷体系间存在排斥作用. 因此, 看似违反常理的阴离子-π相互作用, 自其首次被报道就受到了高度关注, 并迅速在分子识别、催化、自组装、聚集诱导发光材料和新型阴离子受体设计合成等领域展现出了广阔而重要的应用前景. 综述了近10年阴离子-π相互作用在理论计算研究、催化、自组装、受体设计与合成、聚集诱导发光等领域的研究进展, 并对于阴离子-π相互作用在超分子化学领域中的研究与应用进行展望, 为超分子化学研究提供参考.

关键词: 阴离子-π相互作用, 超分子化学, 受体合成, 识别

Anion-π interaction is a non-covalent interaction in host-guest chemistry. In general, aromatic π-systems are regarded as electron rich and may have repulsive interactions with negatively charged systems. Therefore, the anion-π interaction, which seems counterintuitive, has attracted remarkable attention since it was first reported. And surprisingly, it has shown broad and significant potential applications in various fields, including molecular recognition, catalysis, self-assembly, aggregation-induced luminescent materials, and the design and synthesis of novel anionic receptors. This review focuses on the research progress of anion-π interactions in the fields of theoretical studies, catalysis, self-assembly, receptor design and synthesis, and aggregation-induced luminescence in the last decade. Finally, the research and application prospects of anion-π interactions in the field of supramolecular chemistry will be provided.

Key words: anion-π interactions, supramolecular chemistry, receptor synthesis, recognition

引用此文

张晓, 胡密霞, 杜艳青, 梁凤英, 张笑迎, 额尔敦. 阴离子-π相互作用研究进展[J]. 有机化学, 2024, 44(4): 1181-1196.

Xiao Zhang, Mixia Hu, Yanqing Du, Fengying Liang, Xiaoying Zhang, Chaolu Eerdun. Research Progress on Anion-π Interactions[J]. Chinese Journal of Organic Chemistry, 2024, 44(4): 1181-1196.

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图/表 47

图1. C6H6(左)和C6F6(右)的ESP图

Figure 1. ESP maps of C6H6 (left) and C6F6 (right)

图2. 四极矩示意图

Figure 2. Schematic representations of quadrupole moments

图3. 阴离子与π体系的三种相互作用模式

Figure 3. Three modes of interaction of anions with π-systems

图4. 1,3,5-三嗪(1)(左)和三氟-1,3,5-三嗪(2)(右)的结构和ESP图

Figure 4. Structures and ESP of 1,3,5-triazine (1) (left) and trifluoro-1,3,5-triazine (2) (right)

Complex	E/(kJ•mol^–1)	E_int(kJ•mol^–1)	R_e(cation-π)/nm	R_e(anion-π)/nm
Na⁺…C₆H₆	–87.86		0.2429
Na⁺…C₆F₃H₃	–34.35		0.2552
Na⁺…C₆F₆	+14.64		0.2652
C₆H₆…F^–	+11.72			0.3162
C₆H₆…Cl^–	+10.04			0.3731
C₆H₆…Br^–	+7.95			0.3840
Na⁺…C₆H₆…F^–	–389.53	–93.68	0.2280	0.2482
Na⁺…C₆H₆…Cl^–	–356.10	–91.76	0.2304	0.3049
Na⁺…C₆H₆…Br^–	–352.54	–92.55	0.2313	0.3157
Na⁺…C₆F₃H₃…F^–	–380.49	–81.50	0.2353	0.2368
Na⁺…C₆F₃H₃…Cl^–	–336.18	–71.71	0.2389	0.2925
Na⁺…C₆F₃H₃…Br^–	–330.08	–66.94	0.2399	0.3006
Na⁺…C₆H₆…F^–	–369.95	–71.50	0.2437	0.2286
Na⁺…C₆H₆…Cl^–	–316.44	–50.42	0.2488	0.2835
Na⁺…C₆H₆…Br^–	–293.05	–46.99	0.2495	0.2913

表1. 在MP2/6-31++G**基组水平上理论计算研究所得阴离子-π、阳离子-π和π-π相互作用能及其对应的平衡距离(Re)

Table 1. Interaction energies for the investigated anion-π, cation-π, and anion-π-cation complexes on MP2/6-31++G** level of theory and corresponding equilibrum distances (Re)

图5. 苯三酰亚胺笼3的结构

Figure 5. Structure of BTI-based molecular cage 3

图6. BTI晶体结构的(a)俯视图(空腔被DMSO分子占据)和(b)侧视图

Figure 6. (a) Top view (the cavity is occupied by DMSO molecules) and (b) side view of crystal structure of BTI

图7. 化合物4的结构

Figure 7. Structure of compound 4

图8. 化合物5的结构

Figure 8. Structure of compound 5

图9. 化合物6的结构

Figure 9. Structure of compound 6

图10. 加入萘-1,5-二磺酸四丁基铵后CD3CN中6c (1 mmol/L)的化学位移变化

Figure 10. Changes of chemical shifts of 6c (1 mmol/L in CD3CN) upon the addition of tetrabutylammonium naphthlene- 1,5-disulfonate

图11. 大环分子7的结构

Figure 11. Structure of macromolecule 7

图12. 阴离子-π相互作用诱导囊泡自组装形成

Figure 12. Anion-π interactions induce vesicle self-assembly formation

图13. 主体分子8和9的结构

Figure 13. Structures of host molecules 8 and 9

图14. SDS、SLA和SDP的结构

Figure 14. Structures of SDS, SLA and SDP

图15. 化合物13的结构

Figure 15. Structure of compound 13

图式1. 主体分子H和两亲性客体分子G的合成

Scheme 1. Synthesis of the host H and the amphiphilic guest G

图式2. 阴离子-π催化的迈克尔加成反应

Scheme 2. Anion-π-catalyzed Michael addition reactions

图16. 阴离子-π催化剂的结构

Figure 16. Structure of anionic-π catalysts

图17. (a)笼状化合物14的结构、(b, c) [C1?(TolSO3–)3][(n-Bu)4N+]3和(d, e) [C1?–O3S(CH2)3$\text{SO}_{3}^{-}$][Et4N+]2的晶体结构

Figure 17. (a) Structures of cage compounds 14, and crystal structures of (b, c) [C1?($\text{Tol}\text{SO}_{3}^{-}$)3][(n-Bu)4N+]3 and (d,e) [C1?–O3S- (CH2)3$\text{SO}_{3}^{-}$][Et4N+]2

图18. 笼状受体15的结构

Figure 18. Structure of cage receptor 15

图19. 化合物16的结构

Figure 19. Structure of compound 16

图20. 阴离子受体17和18的结构

Figure 20. Anion receptors 17 and 18

图21. 阴离子受体19~21的结构

Figure 21. Structures of anion receptors 19~21

图22. 化合物22和23的结构

Figure 22. Structures of compounds 22 and 23

图23. 受体24的结构

Figure 23. Structure of receptor 24

图24. 阴离子-π受体25的结构

Figure 24. Structure of anion-π receptor 25

图25. 3Ru-[15]PCP-II-6OTf的结构

Figure 25. Structure of 3Ru-[15]PCP-II-6OTf

图26. 3Ru-[15]PCP-II-6OTf晶体结构(重叠构象)的(a)俯视图和(b)侧视图

Figure 26. (a) Top view and (b) side view of crystal structure of 3Ru-[15]PCP-II-6OTf (eclipsed conformation)

图27. 3Ru-[15]PCP-II-6OTf的CD3NO2溶液中加入不同阴离子的四丁基铵盐(1.5 mmol/L, 1∶1物质的量比)时1H NMR谱(600 MHz, 298 K)的变化

Figure27. Changes in 1H NMR spectra (600 MHz, 298 K) upon addition of tetrabutylammonium salts of different anions (1.5 mmol/L, 1∶1 molar ratio) to CD3NO2 solution of 3Ru-[15]PCP- II-6OTf

图28. HD的结构

Figure 28. Structure of HD

图29. 化合物28的结构

Figure 29. Structure of compound 28

图30. 化合物29的结构

Figure 30. Structure of compound 29

图31. 基于阴离子-π相互作用的固有带电AIE系统设计原理

Figure 31. Design rationale of inherent-charged AIE system based on anion-π interactions

图32. TPO-P、TPF和TriPO-PN的结构

Figure 32. Structures of TPO-P, TPF, and TriPO-PN

图33. TPO-P和TriPO-PN与阴离子间的阴离子-π相互作用距离

Figure 33. Anion-π interaction distances between TPO-P and TriPO-PN and anions

图34. 化合物33的结构

Figure 34. Structure of compound 33

图式3. TPI-Si和TPIH-Si之间的可逆转变

Scheme 3. Reversible transformation between TPI-Si and TPIH-Si

图35. TNA的结构

Figure 35. Structure of TNA

图36. 加入不同阴离子水溶液后TG的荧光光谱变化(λex=380 nm)

Figure 36. Fluorescence spectral changes (λex=380 nm) of TG with addition of different anion aqueous solutions

图37. TG (5 mg)的DMSO-d6溶液中加入不同物质的量比的CN–时1H NMR谱的变化

Figure 37. Changes in 1H NMR spectra when different amounts of CN– are added to the DMSO-d6 solution of TG (5 mg) TNA on the left and G on the right. The molar ratios (TG∶CN–) are (a) 1∶0; (b) 1∶0.2 (c) 1∶0.4 (d) 1∶1, and (e) 1∶2, respectively.

图38. 柱[5]芳烃凝胶的结构

Figure 38. Structure of pillar[5]arene-based gelator

图39. 分子识别控制疏水性的两种不同策略示意图

Figure 39. Schematic representation of two different strategies for molecular recognition to control hydrophobicity

图40. 具有生物活性的五元氮杂环化合物的代表性实例

Figure 40. Representative examples of the bioactive five- membered azaheterocyclic compounds

图式4. 化合物43~46的结构

Scheme 4. Structures of compounds 43~46

图41. PTP、PTBF、PTCNC、PTCNP、PTCNBF的结构

Figure 41. Structures of PTP, PTBF, PTCNC, PTCNP, and PTCNBF

图42. 4种阴离子-π型AIE发光物质的结构

Figure 42. Structures of four anion-π type AIE luminescent substances

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