Application of Δ- and Λ-isomerism of octahedral metal complexes for inducing chiral nematic phases

International Journal of Molecular Sciences

Volumn 10, Issue 10, 2009, Pages 4559-4574

  Sato, Hisako ^a,b   Yamagishi, Akihiko ^a  

^a EHIME UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

Chiral; Dopant; Metal complex; Nematic; Twisting power; Vibrational circular dichroism

Indexed keywords

CHROMIUM; COBALT; METAL COMPLEX; RUTHENIUM;

CHEMICAL STRUCTURE; CIRCULAR DICHROISM; ISOMERISM; LIQUID CRYSTAL; NUCLEAR MAGNETIC RESONANCE; REVIEW; ROOM TEMPERATURE;

CHIRAL; DOPANT; METAL COMPLEX; NEMATIC; TWISTING POWER; VIBRATIONAL CIRCULAR DICHROISM;

CHROMIUM; COBALT; COORDINATION COMPLEXES; HYDROXYBUTYRATES; LIQUID CRYSTALS; METALS; PENTANONES; RUTHENIUM; STEREOISOMERISM;

EID: 71649087921     PISSN: None     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/ijms10104559     Document Type: Review

References (43)

1. Kitzerow, H.-S.; Bahr, C. Chirality in Liquid Crystals; Springer-Verlag: New York, NY, USA, 2001.
2. Solladie, G.; Zimmermann, R.G. Liquid crystals: A tool for studies on chirality. Angew. Chem. Int. Ed. 1984, 23, 348-362. (Pubitemid 14640767)
3. Goodby, J.W. Chirality in liquid crystals. J. Mater. Chem. 1991, 1, 307-318.
4. Lee, S.-E.; Raynes, E.P. Transmission and amplification of information and properties in nanostructured liquid crystals. Angew. Chem. Int. Ed. 2008, 47, 2754-2787.
5. Ernst, K.-H. Amplification of chirality in two-dimensional molecular lattices. Curr. Opin. Colloid Interface Sci. 2008, 13, 54-59.
6. Pijper, D.; Feringa, B.L. Control of dynamic helicity at the macro- and supramolecular level. Soft Matter 2008, 7, 1349-1372.
7. Takezoe, H.; Takanishi, Y. Bent-core liquid crystals: Their mysterious and attractive world. Jpn. J. Appl. Phys. PT. 1 2006, 45, 597-625. (Pubitemid 43216216)
8. Hofmeier, H.; Schubert, U.S. Recent developments in the supramolecular chemistry of terpyridine-metal complexes. Chem. Soc. Rev. 2004, 33, 373-399. (Pubitemid 39172100)
9. Link, D.R.; Natale, G.; Shao, R.; Maclennan, J.E.; Clark, N.A.; Körblova, E.; Walba, D.M. Spontaneous formation of macroscopic chiral domains in a fluid smectic phase of achiral molecules. Science 1997, 278, 1924-1927. (Pubitemid 28013229)
10. Di Matteo, A.; Todd, S.M.; Gottarelli, G.; Solladié, G.; Williams, V.E.; Lemieux, R.P.; Ferrarini, A.; Spada, G.P. Correlation between molecular structure and helicity of induced chiral nematics in terms of short-range and electrostatic-induction interactions. The case of chiral biphenyls. J. Am. Chem. Soc. 2001, 123, 7842-7851. (Pubitemid 32899348)
11. Pieraccini, S.; Ferrarini, A.; Spada, G.P. Chiral doping of nematic phases and its application to the determination of absolute configuration. Chirality 2008, 20, 749-759.
12. Ferrarini, A.; Moro, G.J.; Nordio, P.L. Simple molecular model for induced cholesteric phases. Phys. Rev. E 1996, 53, 681-688. (Pubitemid 126583760)
13. Tang, K.; Green, M.M.; Cheon, K.S.; Selinger, J.V.; Garetz, B.A. Chiral conflict. The effect of temperature on the helical sense of a polymer controlled by the competition between structurally different enantiomers: From dilute solution to the lyotropic liquid crystal state. J. Am. Chem. Soc. 2003, 125, 7313-7323.
14. Eelkema, R.; van Delden, R.A.; Feringa, B.L. Direct visual detection of the stereoselectivity of a catalytic reaction. Angew. Chem. Int. Ed. 2004, 43, 5013-5016. (Pubitemid 39330764)
15. Eelkema, R.; Feringa, B.L. Amplification of chirality in liquid crystals. Org. Biomol. Chem. 2006, 4, 3729-3745.
16. Feringa, B.L.; Huck, N.P.M.; van Doren, H.A. Chiroptical switching between liquid crystalline phases. J. Am. Chem. Soc. 1995, 117, 9929-9930.
17. Ruslim, C.; Ichimura, K. Conformational effect on macroscopic chirality modification of cholesteric mesophases by photochromic azobenzene dopants. J. Phys. Chem. B 2000, 104, 6529-6535. (Pubitemid 30904046)
18. Mathews, M.; Tamaoki, N. Planar chiral azobenzenophanes as chiroptic switches for photon mode reversible reflection color control in induced chiral nematic liquid crystals. J. Am. Chem. Soc. 2008, 130, 11409-11416.
19. Mathews, M.; Tamaoki, N. Reversibly tunable helicity induction and inversion in liquid crystal self-assembly by a planar chiroptic trigger molecule. Chem. Commun. 2009, 3609-3611.
20. Ichimura, K. Photoalignment of liquid-crystal systems. Chem. Rev. 2000, 100, 1847-1873.
21. Ikeda, T.; Mamiya, J.-I.; Yu, Y. Photomechanics of liquid-crystalline elastomers and other polymers. Angew. Chem. Int. Ed. 2007, 46, 506-528. (Pubitemid 46159190)
22. Tejedor, R.M.; Oriol, L.; Serrano, J.L.; Sierra, T. Chiral photochemical induction in liquid crystals. J. Mater. Chem. 2008, 18, 2899-2908.
23. Choi, S.-W.; Kawauchi, S.; Ha, N.Y.; Takezoe, H. Photoinduced chirality in azobenzene-containing polymer systems. Phys. Chem. Chem. Phys. 2007, 9, 3671-3681.
24. Matsuoka, Y.; Sato, H.; Yamagishi, A.; Okamoto, K.; Hoshino, N. ΔΛ-Isomerism of mixed 1,3-diketonate complexes of Ru(III) - A designed new source of chirality in nematic liquid crystals. Chem. Mater. 2005, 17, 4910-4917 and references therein. (Pubitemid 41476035)
25. Sato, H.; Yamagishi, A.; Yoshida, J.; Nakano, H.; Hoshino, N. A microscopic model for helical twisting power by the optical isomers of an octahedral metal complex. Jpn. J. App. Phys. 2005, 44, 4067-4072. (Pubitemid 41205475)
26. Sato, H.; Yamagishi, A. Application of the ΔΛ isomerism of octahedral metal complexes as a chiral source in photochemistry. J. Photochem. Photobiol. C: Photochem. Rev. 2007, 8, 67-84. (Pubitemid 47223826)
27. Yoshida, J.; Sato, H.; Yamagishi, A.; Hoshino, N. On the parity in helical twisting power of Ru(III) 1,3-diketonates of C2 symmetry in nematic liquid crystals. J. Am. Chem. Soc. 2005, 127, 8453-8456. (Pubitemid 40828161)
28. Yoshida, J.; Sato, H.; Yamagishi, A.; Hoshino, N. Induction and structural control of chiral nematic phases by the use of photoresponsive tris(β-diketonato) Co(III) and Ru(III) complexes. J. Phys. Chem. B 2008, 112, 9677-9683.
29. Furuno, F.; Sato, H.; Yoshida, Y.; Hoshino, H.; Fukuda, F.; Yamagishi, A. Linkage effects of chromium(III) acetylacetonato units on chiral induction of liquid crystal phases. J. Phys. Chem. B 2007, 111, 521-526. (Pubitemid 46256248)
30. Mitsuoka, T.; Sato, H.; Yoshida, J.; Yamagishi, A.; Einaga, Y. Photomodulation of a chiral nematic liquid crystal by the use of a photoresponsive ruthenium(III) complex. Chem. Mater. 2006, 18, 3442-3447. (Pubitemid 44187534)
31. Taniguchi, T.; Monde, K.; Nishimura, S.-I.; Yoshida, J.; Sato, H.; Yamagishi, A. Rewinding of helical systems by use of the Cr(III) complex as a photoresponsive chiral dopant. Mol. Cryst. Liq. Cryst. 2006, 460, 107-116. (Pubitemid 44956332)
32. Drake, A.F.; Gian, G.G.; Spada, P. The twisting power of some chiral tris-(pentane-2,4-dionato)metal(III) complexes in nematic liquid crystals. Chem. Phys. Lett. 1984, 110, 630-633.
33. Hoshino, N.; Matsuoka, Y.; Okamoto, K.; Yamagishi, A. Δ-[Ru(acac)L] (L = a mesogenic derivative of bpy) as a novel chiral dopant for nematic liquid crystals with large helical twisting power. J. Am. Chem. Soc. 2003, 125, 1718-1719. (Pubitemid 36232565)
34. Zheng, H.; Lai, C.K.; Swager, T.M. Controlling intermolecular interactions between metallomesogens: Side-chain effects in discotic copper, palladium, and vanadyl bis(β-diketonates). Chem. Mater. 1995, 7, 2067-2077.
35. Piao, G.; Akagi, K.; Shirakawa, H. Chiroptical titanium complexes as catalytically active chiral dopants available for asymmetric acetylene polymerization. Synth. Metals 1999, 101, 92-93.
36. Hamakubo, K.; Hama, S.; Yagi, S.; Nakazumi, H.; Mizutani, T. Extraordinary doping effects of chiral helical linear tetrapyrrole-Zn(II) complexes on chiral nematic induction of MBBA liquid crystal. Chem. Lett. 2005, 34, 1454-1455. (Pubitemid 43002454)
37. Braun, M.; Hahn, A.; Engelmann, M.; Fleischer, R.; Frank, W.; Kryschi, C.; Haremza, S.; Kürschner, K.; Parker, R. Bis-chelated imine-alkoxytitanium complexes: Novel chiral dopants with high helical twisting power in liquid crystals. Chem. Eur. J. 2005, 11, 3405-3412. (Pubitemid 40750997)
38. Engelmann, M.; Braun, M.; Kuball, H.-G. Helical twisting power of chiral titanium complexes in nematic compounds. Liq. Cryst. 2007, 34, 73-77.
39. Yamagishi, A.; Taniguchi, M.; Imamura, Y.; Sato, H. Clay column chromatography for optical resolution: Selectivities of Λ-[Ru(phen)] and Λ-[Ru(bpy)] laponite columns towards 1,1′- binaphthol. Appl. Clay Sci. 1996, 11, 1-10.
40. Anzai, N.; Machida, S.; Horie, K. Chirooptical control of liquid crystalline textures containing chromium complex by irradiation of circular polarized light. Chem. Lett. 2001, 888-889. (Pubitemid 33354396)
41. Anzai, N.; Machida, S.; Horie, K. Light-induced control of textures and cholesteric pitch in liquid crystals containing chromium complexes, by means of circular and linear polarized light. Liq. Cryst. 2003, 30, 359-366.
42. Stevenson, K.L. Partial photoresolution. III. The tris(acetylacetonato) chromium(III) system. J. Am. Chem. Soc. 1972, 94, 6652-6654.
43. Choi, S.-W.; Kawauchi, S.; Tanaka, S.; Watanabe, J.; Takezoe, H. Vibrational circular dichroism spectroscopic study on circularly polarized light-induced chiral domains in the B4 phase of a bent mesogen. Chem. Lett. 2007, 36, 1018-1019.