Spontaneous Chirality Induction and Enantiomer Separation in Liquid Crystals Composed of Achiral Rod-Shaped 4-Arylbenzoate Esters

被引:36
作者
Jeong, Hyeon Su [2 ]
Tanaka, Shingo [1 ]
Yoon, Dong Ki [2 ]
Choi, Suk-Won [1 ]
Kim, Yun Ho [2 ]
Kawauchi, Susumu [1 ]
Araoka, Fumito [1 ]
Takezoe, Hideo [1 ]
Jung, Hee-Tae [2 ]
机构
[1] Tokyo Inst Technol, Dept Organ & Polymer Mat, Meguro Ku, Tokyo 1528552, Japan
[2] Korea Adv Inst Sci & Technol, Dept Chem & Biomol Engn BK 21, Taejon 305701, South Korea
关键词
SYMMETRY-BREAKING; SMECTIC PHASE; AMPLIFICATION; COMPOUND; DOMAINS; POWER; C-13;
D O I
10.1021/ja905785d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The discovery of spontaneously induced chirality and enantiomeric separation in liquid crystal and soft crystal systems composed of achiral rod-shaped 4-arylbenzoate esters is described. Negligibly small circular dichroism (CD) signals are produced in the smectic A (SmA) phases of these substances, and the signals were found to increase with increasing smectic order. Since the advent of chirality occurs in freely suspended films, it is not a consequence of surface effects. Both positive and negative CD signals are observed with equal probability at different positions in these films. Vibrational CD spectroscopy and theoretical calculations are used to analyze the conformational changes that are associated with the indued chirality of the rod-shaped molecules. The results show that the phenomenon is caused by thE twisting of biphenyl bond associated with the ester moiety in 4-arylbenzoate esters.
引用
收藏
页码:15055 / 15060
页数:6
相关论文
共 29 条
[1]  
[Anonymous], 2017, J MOL STRUCT, DOI DOI 10.1016/J.MOLSTRUC.2017.03.014
[2]  
AVALOS M, 2000, CHEM COMMUN, V88, P7
[3]   Vibrational circular dichroism spectroscopic study on circularly polarized light-induced chiral domains in the B4 phase of a bent mesogen [J].
Choi, Suk-Won ;
Kawauchi, Susumu ;
Tanaka, Shingo ;
Watanabe, Junji ;
Takezoe, Hideo .
CHEMISTRY LETTERS, 2007, 36 (08) :1018-1019
[4]   Amplification of twisting power in chiral mesophase by introducing achiral rod-like compound with ester group [J].
Choi, Suk-Won ;
Fukuda, Kaoru ;
Nakahara, Shoichiro ;
Kishikawa, Keiki ;
Takanishi, Yoichi ;
Ishikawa, Ken ;
Watanabe, Junji ;
Takezoe, Hideo .
CHEMISTRY LETTERS, 2006, 35 (08) :896-897
[5]   Amplification of chirality in two-dimensional enantiomorphous lattices [J].
Fasel, R ;
Parschau, M ;
Ernst, KH .
NATURE, 2006, 439 (7075) :449-452
[6]   Chiral Isotropic Liquids from Achiral Molecules [J].
Hough, L. E. ;
Spannuth, M. ;
Nakata, M. ;
Coleman, D. A. ;
Jones, C. D. ;
Dantlgraber, G. ;
Tschierske, C. ;
Watanabe, J. ;
Koerblova, E. ;
Walba, D. M. ;
Maclennan, J. E. ;
Glaser, M. A. ;
Clark, N. A. .
SCIENCE, 2009, 325 (5939) :452-456
[7]   Helical Nanofilament Phases [J].
Hough, L. E. ;
Jung, H. T. ;
Krueerke, D. ;
Heberling, M. S. ;
Nakata, M. ;
Jones, C. D. ;
Chen, D. ;
Link, D. R. ;
Zasadzinski, J. ;
Heppke, G. ;
Rabe, J. P. ;
Stocker, W. ;
Koerblova, E. ;
Walba, D. M. ;
Glaser, M. A. ;
Clark, N. A. .
SCIENCE, 2009, 325 (5939) :456-460
[8]   Layer-scale optical chirality of liquid-crystalline phases [J].
Hough, LE ;
Clark, NA .
PHYSICAL REVIEW LETTERS, 2005, 95 (10)
[9]   Generation of a chiral mesophase by achiral molecules: Absolute chiral induction in the smectic C phase of 4-octyloxyphenyl 4-octyloxybenzoate [J].
Kajitani, T ;
Masu, H ;
Kohmoto, S ;
Yamamoto, M ;
Yamaguchi, K ;
Kishikawa, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (04) :1124-1125
[10]   MOLECULAR CHIRALITY AND THE RIPPLE PHASE OF PHOSPHATIDYLCHOLINE MULTIBILAYERS [J].
KATSARAS, J ;
RAGHUNATHAN, VA .
PHYSICAL REVIEW LETTERS, 1995, 74 (11) :2022-2025