Stirring competes with chemical induction in chiral selection of soft matter aggregates

Nature Communications

Volumn 3, Issue , 2012, Pages

  Petit Garrido, Nuria ^a   Claret, Josep ^a   Ignes Mullol, Jordi ^a   Sagues, Francesc ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CHEMICAL MODIFICATION; CHIRALITY; ENANTIOMER; FLOW KINETICS; MICROSCOPY; MIXER; SUPRAMOLECULAR CHEMISTRY;

EID: 84866117666     PISSN: None     EISSN: 20411723     Source Type: Journal    
DOI: 10.1038/ncomms1987     Document Type: Article

References (43)

1. Wagniére, G. H. On Chirality and the Universal Asymmetry: Reflections on Image and Mirror Image (VHCA with Wiley-VCH, 2007).
2. Guijarro, A. & Yus, M. The Origin of Chirality in the Molecules of Life: A Revision from Awareness to the Current Theories and Perspectives of this Unsolved Problem (Royal Society of Chemistry, 2009).
3. Fasel, R., Parschau, M. & Ernst, K. H. Amplification of chirality in twodimensional enantiomorphous lattices. Nature 439, 449-452 (2006). (Pubitemid 43152832)
4. Attard, G. A. Electrochemical studies of enantioselectivity at chiral metal surfaces. J. Phys. Chem. B 105, 3158-3167 (2001).
5. Shiromo, K. et al. Finite enantiomeric excess nucleated in an achiral banana mesogen by chiral alignment surfaces. Angew. Chem. Int. Ed. 44, 1948-1951 (2005).
6. Tortora, L. & Lavrentovich, O. D. Chiral symmetry breaking by spatial confinement in tactoidal droplets of lyotropic chromonic liquid crystals. Proc. Natl Acad. Sci. USA 108, 5163-5168 (2011).
7. Avalos, M. et al. Absolute asymmetric synthesis under physical fields: Facts and fictions. Chem. Rev. 98, 2391-2404 (1998).
8. Barron, L. D. Chirality and life. Space Sci. Rev. 135, 187-201 (2008).
9. Pijper, D. & Feringa, B. L. Control of dynamic helicity at the macro- and supramolecular level. Soft Matter 4, 1349-1372 (2008). (Pubitemid 351877077)
10. Mateos-Timoneda, M. A., Crego-Calama, M. & Reinhoudt, D. N. Supramolecular chirality of self-assembled systems in solution. Chem. Soc. Rev. 33, 363-372 (2004). (Pubitemid 39163827)
11. Yashima, E., Maeda, K., Iida, H., Furusho, Y. & Nagai, K. Helical polymers: synthesis, structures, and functions. Chem. Rev. 109, 6102-6211 (2009).
12. Solladie, G. & Zimmermann, R. G. Liquid-crystals - a tool for studies on chirality. Angew. Chem. Int. Ed. Engl. 23, 348-362 (1984).
13. Huck, N. P. M., Jager, W. F., deLange, B. & Feringa, B. L. Dynamic control and amplification of molecular chirality by circular polarized light. Science 273, 1686-1688 (1996). (Pubitemid 26317778)
14. Iftime, G., Labarthet, F. L., Natansohn, A. & Rochon, P. Control of chirality of an azobenzene liquid crystalline polymer with circularly polarized light. J. Am. Chem. Soc. 122, 12646-12650 (2000). (Pubitemid 32052191)
15. Kim, M. J., Shin, B. G., Kim, J. J. & Kim, D. Y. Photoinduced supramolecular chirality in amorphous azobenzene polymer films. J. Am. Chem. Soc. 124, 3504-3505 (2002).
16. Choi, S. W. et al. Circular-polarization-induced enantiomeric excess in liquid crystals of an achiral, bent-shaped mesogen. Angew. Chem. Int. Ed. 45, 1382-1385 (2006).
17. Rikken, G. L. J. A. & Raupach, E. Enantioselective magnetochiral photochemistry. Nature 405, 932-935 (2000). (Pubitemid 30435045)
18. McBride, J. M. & Tully, J. C. Physical chemistry - did life grind to a start? Nature 452, 161-162 (2008). (Pubitemid 351380232)
19. Noorduin, W. L. et al. Emergence of a single solid chiral state from a nearly racemic amino acid derivative. J. Am. Chem. Soc. 130, 1158-1159 (2008). (Pubitemid 351170993)
20. Viedma, C. Chiral symmetry breaking during crystallization: complete chiral purity induced by nonlinear autocatalysis and recycling. Phys. Rev. Lett. 94, 065504 (2005).
21. Kondepudi, D. K., Kaufman, R. J. & Singh, N. Chiral symmetry-breaking in sodium-chlorate crystallization. Science 250, 975-976 (1990).
22. Micali, N. et al. Selection of supramolecular chirality by application of rotational and magnetic forces. Nat. Chem. 4, 201-207 (2012).
23. Barron, L. D. Spin and gravity give a helping hand. Nat. Chem. 4, 150-152 (2012).
24. Ribo, J. M., Crusats, J., Sagues, F., Claret, J. & Rubires, R. Chiral sign induction by vortices during the formation of mesophases in stirred solutions. Science 292, 2063-2066 (2001). (Pubitemid 32694379)
25. Crusats, J., El-Hachemi, Z. & Ribo, J. M. Hydrodynamic effects on chiral induction. Chem. Soc. Rev. 39, 569-577 (2010).
26. Petit-Garrido, N., Ignes-Mullol, J., Claret, J. & Sagues, F. Chiral selection by interfacial shearing of self-assembled achiral molecules. Phys. Rev. Lett. 103, 237802 (2009).
27. Chen, P., Ma, X., Hu, K., Rong, Y. & Liu, M. Left or right? The direction of compression-generated vortex-like flow selects the macroscopic chirality of interfacial molecular assemblies. Chemistry 17, 12108-12114 (2011).
28. Ohno, O., Kaizu, Y. & Kobayashi, H. J-aggregate formation of a water-soluble porphyrin in acidic aqueous-media. J. Chem. Phys. 99, 4128-4139 (1993).
29. Tsuda, K. et al. Spectroscopic visualization of vortex flows using dye-containing nanofibers. Angew. Chem. Int. Ed. 46, 8198-8202 (2007).
30. Wolffs, M. et al. Macroscopic origin of circular dichroism effects by alignment of self-assembled fibers in solution. Angew. Chem. Int. Ed. 46, 8203-8205 (2007). (Pubitemid 350096598)
31. Spada, G. P. Alignment by the convective and vortex flow of achiral selfassembled fibers induces strong circular dichroism effects. Angew. Chem. Int. Ed. 47, 636-638 (2008).
32. Arteaga, O. et al. Reversible mechanical induction of optical activity in solutions of soft-matter nanophases. Chem. Asian J. 4, 1687-1696 (2009).
33. Arteaga, O. et al. Emergence of supramolecular chirality by flows. Chemphyschem 11, 3511-3516 (2010).
34. D'Urso, A., Randazzo, R., Lo Taro, L. & Purrello, R. Vortexes and nanoscale chirality. Angew. Chem. Int. Ed. 49, 108-112 (2010).
35. Nandi, N. & Vollhardt, D. Effect of molecular chirality on the morphology of biomimetic Langmuir monolayers. Chem. Rev. 103, 4033-4075 (2003).
36. Viswanathan, R., Zasadzinski, J. A. & Schwartz, D. K. Spontaneous chiralsymmetry breaking by achiral molecules in a Langmuir-Blodgett-film. Nature 368, 440-443 (1994). (Pubitemid 24116998)
37. Ignes-Mullol, J. et al. Texture changes inside smectic-C droplets in azobenzene langmuir monolayers. Langmuir 21, 2948-2955 (2005). (Pubitemid 40448960)
38. Vlahakis, J. Z., Wand, M. D. & Lemieux, R. P. Photoinduced polarization inversion in a ferroelectric liquid crystal using an ambidextrous chiral thioindigo dopant. J. Am. Chem. Soc. 125, 6862-6863 (2003). (Pubitemid 36682773)
39. Eelkema, R. et al. Rotational reorganization of doped cholesteric liquid crystalline films. J. Am. Chem. Soc. 128, 14397-14407 (2006). (Pubitemid 44707750)
40. Warner, M., Terentjev, E., Meyer, R. & Mao, Y. Untwisting of a cholesteric elastomer by a mechanical field. Phys. Rev. Lett. 85, 2320-2323 (2000).
41. Barlow, S. M. & Raval, R. Complex organic molecules at metal surfaces: bonding, organisation and chirality. Surf. Sci. Rep. 50, 201-341 (2003).
42. Kuzmenko, I. et al. Design and characterization at crystalline thin film architectures at the air-liquid interface: Simplicity to complexity. Chem. Rev. 101, 1659-1696 (2001). (Pubitemid 35377800)
43. Rasband, W. S. ImageJ National Institutes of Health, 1997-2012).