Research Progress on Anion-π Interactions

doi:10.6023/cjoc202308003

Abstract

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

Cite this article

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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Fig. & Tab. 47

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

Figure 2. Schematic representations of quadrupole moments

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

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

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)

Figure 5. Structure of BTI-based molecular cage 3

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

Figure 7. Structure of compound 4

Figure 8. Structure of compound 5

Figure 9. Structure of compound 6

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

Figure 11. Structure of macromolecule 7

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

Figure 13. Structures of host molecules 8 and 9

Figure 14. Structures of SDS, SLA and SDP

Figure 15. Structure of compound 13

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

Scheme 2. Anion-π-catalyzed Michael addition reactions

Figure 16. Structure of anionic-π catalysts

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

Figure 18. Structure of cage receptor 15

Figure 19. Structure of compound 16

Figure 20. Anion receptors 17 and 18

Figure 21. Structures of anion receptors 19~21

Figure 22. Structures of compounds 22 and 23

Figure 23. Structure of receptor 24

Figure 24. Structure of anion-π receptor 25

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

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

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

Figure 28. Structure of HD

Figure 29. Structure of compound 28

Figure 30. Structure of compound 29

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

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

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

Figure 34. Structure of compound 33

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

Figure 35. Structure of TNA

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

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.

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

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

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

Scheme 4. Structures of compounds 43~46

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

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

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