Fabrication and Applications of Supramolecular Chiral Assemblies

doi:10.6023/cjoc202008011

Abstract

As a kind of soft materials promoted by multiple noncovalent interactions, supramolecular chiral assemblies own the distinctive confined chiral microenvironment and play an important role in material engineering, life science, optical devices and catalytic synthesis. In general, supramolecular chiral assembles can be fabricated through the assembly of chiral molecules, or a combination of achiral molecules and chiral inducements, or mere achiral molecules in symmetry breaking manner. In this paper, the general fabrication strategies of supramolecular chiral assemblies in recent years are summarized, and their improvements in chiral template, chiral recognition, circularly polarized luminescence and asymmetric catalysis are briefly reviewed, as well as the shortcomings in these fields. With the development of supramolecular chiral assemblies, the mechanism of chirality transfer will be explained in depth in future, which may help us understand the chirality phenomenon in organism and give a clue to answer to the origin of homochirality in nature.

Key words: supramolecular chiral assembly, chiral template, chiral recognition, circularly polarized luminescence, asymmetric catalysis

Cite this article

Jinguo Liu, Feng Yin, Jun Hu, Yong Ju. Fabrication and Applications of Supramolecular Chiral Assemblies[J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1031-1052.

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Fig. & Tab. 40

Figure 1. (a) Chemical structures of D-glucose-based amphiphile 1 and TEM image of its assembly[19], and (b) chemical structures of Fmoc-D-glucosamine 2 and Fmoc-D-glucosamine 3[20]

Figure 2. Illustration of the self-assembly for twisted ribbons and microplates of 4[22]

Figure 3. Disaccharide-azobenzene compounds 5~7, and in situ LVSEM images of their assemblies (a) 5 and (b) 6 (scale bar: 1 μm) [25]

Figure 4. Chemical structures of D-phenylalanine derivatives 8~9 and SEM images of assemblies of (a) 8 and (b) 9[28]

Figure 5. Chemical structures of Bola-type valine-based amphiphiles DD-10 and LL-10[29]

Figure 6. (a) Chemical structures of D/L-11, 12, 13 and illustration of the formation of metallacycles rhomboids and hexagons, SEM images of gels of (b) D-14, (c) L-14, (d) D-15, (e) L-15 (Inset: corresponding TEM images)[30]

Figure 7. Chemical structures of D/L-16 and SEM images of their co-assemblies with various ee values (scale bar: 5 μm) [31]

Figure 8. Chemical structures of D/L-17 and illustration of the linear supramolecular structure assembled form D/L-17 and Ag+[32]

Figure 9. Chemical structure of cholesterol-azopyridine conjugate 18, and control on dimensions and supramolecular chirality of it sassemblies through UV and metal ions[38]

Figure 10. Chemical structures of bile acid derivatives 19~21, and SEM images of assemblies of 19 (a) and 20 (b)[39]

Figure 11. Illustration of right-handed fibrils assembled from 22 in water[43]

Figure 12. CD spectra signal of cresol red induced by 23[44]

Figure 13. Helical assemblies constructed by triterpenoid-pyridinium 24~27[45]

Figure 14. Chemical structures of C3-symmetrical 28 and 29, and illustration of their helical assemblies[51]

Figure 15. Chemical structures of 30, 31 and CD spectra of co-assemblies at different ratio of 31 in (a) n-heptane and (b) toluene[53]

Figure 16. (a) Chemical structures of D/L-32, 33, 34 and the chiral complexes of D-32+34 and L-32+34, (b) CD spectra versus different molar fractions of D/L-32 in the mixtures of D/L-32 and 34 (■ D-32, ▲ L-32), and (c) plot of CD intensity at 315 nm versus different ee values of mixed D/L-32 (■ ee of L-32, ▲ ee of D-32)[54]

Figure 17. Chemical structures of carotenoids 35~37[55]

Figure 18. Manipulation of supramolecular chiral assembly of 38 by circularly polarized light[61]

Figure 19. Chemical structure of 39 and CD spectra of chiral assemblies of 39 induced by CPL at (a) 365 nm (b) 313 nm[62]

Figure 20. Chemical structure of 40 and supramolecular chirality of assembled 40 induced by vortex and efficient gravity[64]

Figure 21. Chemical structure of 41 and the proposed chiral model of 41-Ag(I)[70]

Figure 22. (a) Chemical structures of 42, 43 and their hexamer, and (b) CD spectra of 40 independent assemblies[73]

Figure 23. Chemical structure of 44 and illustration of symmetry breaking, chiral induction and chiral memory of 44 gel[74]

Figure 24. (a) Chemical structures of 45, 46 and illustration of their chiral assemblies, and (b, c) chiral domains with opposite handedness (bright/dark) in assemblies[75]

Figure 25. Schematic of self-assembly process of 47 and chirality imprinting from helical-assembled 47 to inorganic silica[79]

Figure 26. Chemical structures of D/L-48, 49 and supramolecular structures of twisted nanoribbons and double-helical Au nanowires fabricated by D-48 and 49[80]

Figure 27. Self-assembly of amphiphile 50 and DNA-directed chiral organization of AuNPs and AuNRs[81]

Figure 28. Fabrication of helical MOF nanostructures by supramolecular assembly templates of D/L-51[82]

Figure 29. Chemical structure of 52 and response of vesicles self-assembled from 52 to D/L-tartrate monitored by DLS[85]

Figure 30. Structure model of assemblies 53 and its responses to R/S-TBSA[86]

Figure 31. Chemical structure of 54 and fluorescent change of assembled 54 in the presence of RR/SS-CHDA[87]

Figure 32. Chemical structures of 56, R-56 and schematic representation of their co-assembly and enantioselective recognition[88]

Figure 33. Chemical structure of 57[91]

Figure 34. Chiral AIE-active molecule 58 and TEM image of its assembly[93]

Figure 35. Chemical structure of 59 and CPL spectra of fluorescent dye co-assembled with 59[94]

Figure 36. Chemical structures of 60, QDs and the full-color CPL spectra of their co-assemblies[95]

Figure 37. Chemical structures of 61~63[100-101]

Figure 38. Nanotubes self-assembled from 64 and the asymmetric aldol reaction catalyzed by these nanotubes[102]

Figure 39. Chemical structures of 65, 66 and the asymmetric hydrogenation catalyzed by nanorods of 65[103]

Figure 40. Chemical structures and AFM images of the helical assemblies of (a) L-67 and (b) D-67[104], and (c) proposed mechanism of asymmetric Diels-Alder reaction catalyzed by helical nanotubes[105]

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