Chiral doping of nematic phases and its application to the determination of absolute configuration

Chirality

Volumn 20, Issue 5, 2008, Pages 749-759

  Pieraccini, Silvia ^a   Ferrarini, Alberta ^b   Spada, Gian Piero ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b UNIVERSITY OF PADOVA   (Italy)

Author keywords

Absolute configuration; Cholesteric induction; Helical twisting power; Liquid crystal; Nematic

Indexed keywords

CHEMICAL STRUCTURE; CHIRALITY; LIQUID CRYSTAL; MOLECULAR RECOGNITION; PRIORITY JOURNAL; REVIEW; STEREOCHEMISTRY;

EID: 43249107712     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20482     Document Type: Review

References (95)

1. Reinitzer F. Beiträge zur Kenntniss des Cholesterinse für Chemie. Monatsh Chem 1888;9:421-441.
2. Bahadur B, editor. Liquid crystals - Applications and uses. Singapore: World Scientific; 1990.
3. Collins PJ, Hird M. Introduction to liquid crystals - Chemistry and physics. London: Taylor and Francis; 1997.
4. Dierking I. Textures of liquid crystals. Weinheim: Wiley-VCH; 2003.
5. Demus D, Goodby J, Gray GW, Spiess HW, Vill V, editors. Handbook of liquid crystals. Weinheim: Wiley-VCH; 1998.
6. Kitzerow HS, Bahr C, editors. Chirality in liquid crystals. New York: Springer-Verlag; 2001.
7. Friedel G. The mesomorphic states of matter. Ann Phys 1922;18:273-474.
8. Buckingham AD, Ceasar GP, Dunn MB. The addition of optically active compounds to nematic liquid crystals. Chem Phys Lett 1969; 3:540-541.
9. Korte EH. Discrimination of enantiomers at microgram level using liquid crystalline solutions. Appl Spectrosc 1978;32:568-572.
10. Solladié G, Zimmermann R. Liquid crystals: A tool for studies on chirality. Angew Chem Int Ed Eng 1984;23:348-362.
11. Hakemi H, Varanasi PP. The determination of cholesteric pitch from the diffusion profile a new experimental approach. Liq Cryst 1986;1: 63-71.
12. Chilaya GS, Lisetski LN. Cholesteric liquid crystals: Physical properties and molecular-statistical theories. Mol Cryst Liq Cryst 1986;140: 243-286.
13. De Vries H. Rotatory power and other optical properties of certain liquid crystals. Acta Crystallog 1951;4:219-226.
14. Grandjean F. The existence of equidistant layers normal to the optic axis in anisotropic liquids (liquid crystals). Compt Rend 1921;172:71-74.
15. Cano R. An explanation of Grandjean discontinuities. Bull Soc Fr Mineral 1968;91:20-27.
16. Heppke G, Oestreicher F. Determination of the helical sense of cholesteric liquid crystals using the Grandjean-Cano method. Z Naturforsch (A) 1977;32:899-901.
17. Heppke G, Oestreicher F. Determination of the cholesteric screw sense. Mol Cryst Liq Cryst 1978;41:245-249.
18. Kahn FJ. Electric-field-induced color changes and pitch dilation in cholesteric liquid crystals. Phys Rev Lett 1970;24:209-212.
19. Eelkema R, Pollard MM, Katsonis N, Vicario J, Broer DJ, Feringa BL. Rotational reorganization of doped cholesteric liquid crystalline films. J Am Chem Soc 2006;128:14397-14407.
20. Eelkema R, Pollard MM, Vicario J, Katsonis N, Ramon BS, Bastiaansen CWM, Broer DJ, Feringa BL. Nanomotors rotates microscale objects. Nature 2006;440:163.
21. Eelkema R, Feringa BL. Amplification of chirality in liquid crystals. Org Biomol Chem 2006;4:3729-3745.
22. Ichimura K. Photoalignment of liquid-crystal systems. Chem Rev 2000;100:1847-1873.
23. Ikeda T, Kanazawa A. In: Feringa BL, editor. Molecular switches. Weinheim: Wiley-VCH; 2001. p 363-397.
24. Ikeda T. Photomodulation of liquid crystal orientations for photonic applications. J Mater Chem 2003;13:2037-2057.
25. Proni G, Spada GP. Doped nematic phases: A tool for amplifying and detecting chirality. Enantiomer 2001;6:171-179.
26. Kuball HG, Höfer T. From a chiral molecule to a chiral anisotropic phase. In: Bahr CH, Kitzerow HS, editors. Chirality in liquid crystals. New York: Springer-Verlag; 2001. p 67-100.
27. Penot JP, Jacques J, Billard J. Reducing the part of chance in research on spontaneous resolution. II. A microdiagnostic technique for optical activity and its application. Tetrahedron Lett 1968;37:4013-4016.
28. Bertocchi G, Gottarelli G, Prati R. Determination of heroin by means of the pitch of induced cholesteric mesophases. Talanta 1984;31:138-140.
29. Gottarelli G, Samorì B, Fuganti C, Grasselli C. Liquid crystal characterization of compounds chiral by deuterium substitution. J Am Chem Soc 1981;103:471-472.
30. Kuball HG, Weiß B, Beck AK, Seebach D. TADDOLs with unprecedented helical twisting power in liquid crystals. Preliminary communication. Helv Chim Acta 1997;80:2507-2514.
31. Seebach D, Beck AK, Heckel A. TADDOLs, their Derivatives, and TADDOL analogues: Versatile chiral auxiliaries. Angew Chem Int Ed 2001;40:92-138.
32. Van Delden RA, Feringa BL. Color indicators of molecular chirality based on doped liquid crystals. Angew Chem Int Ed 2001;40:3198-3200.
33. Van Delden RA, Feringa BL. Colour indicator for enantiomeric excess and assignment of the configuration of the major enantiomer of an amino acid ester. Chem Commun 2002;174-175.
34. Eelkema R, van Delden RA, Feringa BL. Direct visual detection of the stereoselectivity of a catalytic reaction. Angew Chem Int Ed 2004;43:5013-5016.
35. Zahn S, Proni G, Spada GP, Canary JW. Supramolecular detection of metal ion binding: ligand conformational control of cholesteric induction in nematic liquid crystalline phases. Chem Eur J 2001;7: 88.
36. 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.
37. Drake AF, Gottarelli G, Spada GP. The twisting power of some chiral tris(pentane-2,4-dionate)metal(III) complexes in nematic liquid crystals. Chem Phys Lett 1984;110:630-633.
38. Eelkema R, Feringa BL. Macroscopic expression of the chirality of amino alcohols by a double amplification mechanism in liquid crystalline media. J Am Chem Soc 2005;127:13480-13481.
39. Eelkema R, Feringa BL. Phosphoric acids as amplifiers of molecular chirality in liquid crystalline media. Org Lett 2006;8:1331-1334.
40. Gottarelli G, Spada GP. Induced cholesteric mesophases: origin and applications. Mol Cryst Liq Cryst 1985;123:377-388.
41. Gottarelli G, Spada GP, Solladié G. Some stereochemical applications of induced cholesteric liquid crystals. Nouv J Chim 1986;10:691-696.
42. Spada GP, Proni G. The nematic liquid crystal phase as a probe of the molecular shape helicity. Enantiomer 1998;3:301-314.
43. Gottarelli G, Samorì B, Marzocchi S, Stremmenos C. Induction of a cholesteric mesophase in a nematic liquid crystal by some optically active alcohols. Possible method for the correlation of configurations. Tetrahedron Lett 1975;24:1981-1984.
44. Krabbe HJ, Heggemeier H, Schrader B, Korte EH. Relationship between the infrared rotatory dispersion of liquid-crystalline solutions of chiral molecules and their absolute configuration. Angew Chem Int Ed Eng 1977;16:791-792.
45. Krabbe HJ, Heggemeier H, Schrader B, Korte EH. Determination of the absolute configuration of chiral molecules from the infrared rotatory dispersion of their liquid-crystalline solutions. J Chem Res (S) 1978;238. J Chem Res (M) 1978;3023-3040.
46. Korte EH, Schrader B, Bualek S. A new method for the study of molecular chirality: Infrared rotatory dispersion of induced cholesteric solutions. J Chem Res (S) 1978;236-237. J Chem Res (M) 1978;3001-3022.
47. Gottarelli G, Samorì B, Folli U, Torre G. Induction of cholesteric mesophases in nematic liquid crystals by some optically active sulfoxides: Relationship between the absolute configurations, the dimensions of the substituents and the handness of the induced mesophases. J Phys (C) 1979;40:25-26.
48. 2-symmetric 1,1′-binaphthyl derivatives by circular dichroism spectroscopy and cholesteric induction in nematic mesophases. J Org Chem 2000;65:5522-5527.
49. Superchi S, Donnoli MI, Proni G, Spada GP, Rosini C. Induction of cholesteric mesophases by simple cyclic derivatives of p,p′- disubstituted 1,2-diphenylethane-1,2-diols: Importance of shape and electronic factors. J Org Chem 1999;64:4762-4767.
50. Gottarelli G, Mariani P, Spada GP, Samorì B, Forni A, Solladié G, Hibert M. Induction of cholesteric mesophases in nematic liquid crystals and correlation of absolute configurations of some chiral oxiranes and thiiranes. Tetrahedron 1983;39:1337-1344.
51. Gottarelli G, Samorì B, Stremmenos C, Torre G. Induction of cholesteric mesophases in nematic liquid crystals by some chiral aryl alkyl carbinols. Tetrahedron 1981;37:395-399.
52. Suchod B, Renault A, Lajzerowicz J, Spada GP. A study of the conformation of some chiral binaphthyl and bithienyl derivatives in the solid state and in solution. An approach by X-ray diffraction, circular dichroism spectroscopy and induced cholesteric mesophase analysis. J Chem Soc Perkin Trans 2 1992;1839-1844.
53. Rinaldi PL, Wilk M. Use of liquid crystal induced circular dichroism for absolute configurational assignments of β-amino alcohols. J Org Chem 1983;48:2141-2146.
54. Mioskowski C, Bourguignon J, Candau S, Solladié G. Photochemically induced cholesteric-nematic transition in liquid crystals. Chem Phys Lett 1976;38:456-459.
55. Gottarelli G, Hibert M, Samorì B, Solladié G, Spada GP, Zimmermann R. Induction of the cholesteric mesophase in nematic liquid crystals: Mechanism and application to the determination of bridged biaryl configuration. J Am Chem Soc 1983;105:7318-7321.
56. Gottarelli G, Spada GP, Varech D, Jacques J. All-trans 2,7-dialkylperhydrophenantrene as a solvent for measurements of helical twisting power and linear dichroism. Liq Cryst 1986;1:29-35.
57. Memmer R, Kuball HG, Schönhofer A. Computer simulation of chiral liquid crystal phases. III. A cholesteric phase formed by chiral Gay-Berne atropisomers. Mol Phys 1996;89:1633-1649.
58. Gottarelli G, Osipov MA, Spada GP. A study of solvent effect on the optical rotation of chiral biaryls. J Phys Chem 1991;95:3879-3884.
59. Bandini M, Casolari S, Cozzi PG, Proni G, Schmohel E, Spada GP, Tagliavini E, Umani Ronchi A. Synthesis and characterization of new enantiopure 7,7′-disubstituted 2,2′-dihydroxy-1,1′-binaphthyls: Useful ligands for the asymmetric allylation reaction of aldehydes. Eur J Org Chem 2000;491-497.
60. Gottarelli G, Spada GP, Bartsch R, Solladié G, Zimmermann R. Induction of the cholesteric mesophase in nematic liquid crystals: correlation between the conformation of open-chain chiral 1,1′-binaphthyls and their twisting powers. J Org Chem 1986;51:589-592.
61. Rosini C, Rosati I, Spada GP. A conformational analysis of mono and dialkyl ethers of 2,2′-dihydroxy-1,1′-binaphthalene by circular dichroism spectroscopy and cholesteric induction in nematic liquid crystals. Chirality 1995;7:353-358.
62. Deussen HJ, Shibaev PV, Vinokur R, Bjornholm T, Schaumburg K, Bechgaard K, Shibaev VP. New 6,6′-disubstituted-binaphthol derivatives as chiral dopants: Synthesis and temperature dependence of molecular conformations. Liq Cryst 1996;21:327-340.
63. Goossens WJA. Molecular theory of the cholesteric phase and of the twisting power of optically active molecules in a nematic liquid crystal. Mol Cryst Liq Cryst 1971;12:237-244.
64. Stegemeyer H, Finkelmann H. Temperature dependence of helical pitch of induced cholesteric mesophases. Naturwiss 1975;62:436-437.
65. Van der Meer BW, Vertogen G. The helix inversion in cholesteric-nematic mixtures. Phys Lett (A) 1979;74:242-244.
66. Allen MP. Calculating the helical twisting power of dopants in a liquid crystal by computer simulation. Phys Rev (E) 1993;47:4611-4614.
67. Emelyanenko AV, Osipov MA, Dunmur DA. Molecular theory of helical sense inversions in chiral nematic liquid crystals. Phys Rev (E) 2000;62:2340-2352.
68. Berardi R, Kuball HK, Memmer R, Zannoni C. Chiral induction in nematics. A computer simulation study. J Chem Soc Farad Trans 1998;94:1229-1234.
69. Cook MJ, Wilson MR. Calculation of helical twisting power for liquid crystal chiral dopants. J Chem Phys 2000;112:1560-1564.
70. Ferrarini A, Moro GJ, Nordio PL. Simple molecular model for induced cholesteric phases. Phys Rev (E) 1996;53:681-688.
71. Ferrarini A, Moro GJ, Nordio PL. Shape model for ordering properties of molecular dopants inducing chiral mesophases. Mol Phys 1996;87:485-499.
72. Eisenberg D, McLachlan A. Solvation energy in protein folding and binding. Nature 1986;319:199-203.
73. Ooi T, Oobatake M, Nemethy G, Scheraga HA. Accessible surface areas as a measure of the thermodynamic parameters of hydration of peptides. Proc Natl Acad Sci USA 1987;84:3086-3090.
74. Still WC, Tempvzyk A, Hawley RC, Hendrickson T. Semianalytical treatment of solvation for molecular mechanics and dynamics. J Am Chem Soc 1990;112:6127-6129.
75. Cramer CJ, Truhlar DG. Implicit solvation models: equilibria, etructure, spectra, and dynamics. Chem Rev 1999;99:2161-2200.
76. Ferrarini A, Janssen F, Moro GJ, Nordio PL, Molecular surface and order parameters in liquid crystals. Liq Cryst 1999;26:201-210.
77. Richards FM. Areas, volumes, packing and protein structure. Ann Rev Biophys Bioeng 1997;151-176.
78. Connolly ML. Analytical molecular surface calculation. J Appl Cryst 1983;548-558.
79. Osipov MA, Pickup BT, Dunmur DA. A new twist on molecular chirality: Intrinsic chirality indices. Mol Phys 1995;84:1193-1206.
80. Solymosi M, Low RJ, Grayson M, Neal MP. A generalized scaling of chiral indices for molecules. J Chem Phys 2002;116:9875-9881.
81. Neal MP, Solymosi M, Wilson MR, Earl DJ. Helical twisting power and scaled chiral indices. J Chem Phys 2003;119:3567-3573.
82. Kamberaj H, Osipov MA, Low RJ, Neal MP. Helical twisting power and chirality indices. Mol Phys 2004;102:431-446.
83. Kamberaj H, Low RJ, Neal MP. Correlation between molecular chirality and helical twisting power a computer simulation study. Mol Phys 2006;104:335-357.
84. Ferrarini A, Nordio PL. On the assessment of molecular chirality. J Chem Soc Perkin Trans 2 1998;455-460.
85. Gottarelli G, Spada GP, Seno K, Hagishita S, Kuriyama K. Induced cholesteric mesophases as a probe for the stereochemistry of chiral biphenyls. Bull Chem Soc Jpn 1986;56:1607-1608.
86. Williams VE, Lemieux RP. Substituent effects in the induction of a cholesteric liquid crystal phase by atropisomeric dibenzoxepins: A study of arene-arene interactions. Chem Commun 1996;2259-2260.
87. Di Matteo A, Todd SM, Gottarelli G, Solladié G, Williams VE, Lemieux RP, Ferrarini A, Spada GP. Correlation between molecular structure and helicity of induced chiral nematics in terms of short-range and electrostatic-induction interactions. J Am Chem Soc 2001;123:7842-7851.
88. Gottarelli G, Hansen H-J, Spada GP, Weber RH. A liquid crystal study of heptalene. Helv Chim Acta 1987;70:430-435.
89. Gottarelli G, Proni G, Spada GP, Fabbri D, Gladiali S, Rosini C. Conformational and configurational analysis of 4,4′-biphenanthryl derivatives and related helicenes by circular dichroism spectroscopy and cholesteric induction in nematic mesophases. J Org Chem 1996; 61:2013-2019.
90. Ferrarini A, Gottarelli G, Nordio PL, Spada GP. Determination of the absolute configuration of helicenes and related biaryls from calculation of helical twisting powers by the surface chirality model. J Chem Soc Perkin Trans 2 1999;411-417.
91. Pieraccini S, Ferrarini A, Kaoro F, Gottarelli G, Lena S, Tsubaki K, Spada GP. Homochiral helices inducing opposite-handed cholesteric phases. Chem Eur J 2006;12:1121-1126.
92. Ferrarini A, Nordio PL, Shibaev PV, Shibaev VP. Twisting power of bridged binaphthol derivatives: Comparison of theory and experiment. Liq Cryst 1998;24:219-227.
93. Earl DJ, Wilson MR. Predictions of molecular chirality and helical twisting powers: Atheoretical study. J Chem Phys 2003;119:10280-10288.
94. Pieraccini S, Donnoli MI, Ferrarini A, Gottarelli G, Ucini G, Rosini C, Superchi S, Spada GP. A correlation between the absolute configuration of alkyl aryl sulfoxides and their helical twisting power in nematic liquid crystals. J Org Chem 2003;68:519-526.
95. Celebre G, de Luca G, Maiorino M, Iemma F, Ferrrarini A, Pieraccini S, Spada GP. Solute-solvent interactions and chiral induction in liquid crystals. J Am Chem Soc 2005;127:11736-11744.