Molecular design of nonchiral bent-core liquid crystals with antiferroelectric properties

Journal of the American Chemical Society

Volumn 122, Issue 8, 2000, Pages 1593-1601

  Shen, Dong ^a   Pegenau, Annegret ^a   Diele, Siegmar ^a   Wirth, Ina ^a   Tschierske, Carsten ^a  

^a MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CHEMICAL STRUCTURE; DIFFERENTIAL SCANNING CALORIMETRY; LIQUID CRYSTAL; MOLECULAR STABILITY; PHOTOCHEMISTRY; POLARIZATION; STRUCTURE ANALYSIS; X RAY ANALYSIS;

EID: 0034091807     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja993572w     Document Type: Article

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48. Examples for the stabilization of liquid crystalline phases by perfluorinated chains: (a) Viney, C.; Twieg, R, J.; Russell, T. P.; Depero, L. E. Liq. Cryst. 1989, 5, 1783. (b) Doi, T.; Sakurai, Y.; Tamatani, A.; Takenaka, S.; Kusabashi, S.; Nishihata, Y.; Terauchi, H. J. Mater. Chem. 1991, 1, 169. (c) Nguyen, H. T.; Sigaud, G.; Achard, M. F.; Hardouin, F.; Twieg, R. J.; Betterton, K. Liq. Cryst. 1991, 10, 389. (d) Pensec, S.; Tournilhac, F.-G.; Bassoul, P. J. Phys. II Fr. 1996, 6, 1597. (e) Arehart, S. V.; Pugh, C. J. Am. Chem. Soc. 1997, 119, 3027. (f) Takenaka, S. J. Chem. Soc., Chem. Commun. 1992, 1748. (g) Johansson, G.; Percec, V.; Ungar, G.; Smith, K. Chem. Mater. 1997, 9, 164. (h) Dahn, U.; Erdelen, C.; Ringsdorf, H.; Festag, R.; Wendorff, J. H.; Heiney, P. A.: Maliszewskyj, N. C. Liq. Cryst. 1995, 19, 759. (i) Percec, V.; Schlueter, D.; Kwon, Y. K.; Blackwell, J.; Möller, M.; Slangen, P. J. Macromolecules 1995, 28, 8807. (j) Reference 27. (k) Pegenau, A.; Cheng, X. H.; Tschierske, C.; Göring, P.; Diele, S. New J. Chem. 1999, 23, 465. (l) Cheng, X. H.; Diele, S.; Tschierske, C. Angew. Chem., Int. Ed. Engl. 2000, 39, 592.
49. Examples for the stabilization of liquid crystalline phases by perfluorinated chains: (a) Viney, C.; Twieg, R, J.; Russell, T. P.; Depero, L. E. Liq. Cryst. 1989, 5, 1783. (b) Doi, T.; Sakurai, Y.; Tamatani, A.; Takenaka, S.; Kusabashi, S.; Nishihata, Y.; Terauchi, H. J. Mater. Chem. 1991, 1, 169. (c) Nguyen, H. T.; Sigaud, G.; Achard, M. F.; Hardouin, F.; Twieg, R. J.; Betterton, K. Liq. Cryst. 1991, 10, 389. (d) Pensec, S.; Tournilhac, F.-G.; Bassoul, P. J. Phys. II Fr. 1996, 6, 1597. (e) Arehart, S. V.; Pugh, C. J. Am. Chem. Soc. 1997, 119, 3027. (f) Takenaka, S. J. Chem. Soc., Chem. Commun. 1992, 1748. (g) Johansson, G.; Percec, V.; Ungar, G.; Smith, K. Chem. Mater. 1997, 9, 164. (h) Dahn, U.; Erdelen, C.; Ringsdorf, H.; Festag, R.; Wendorff, J. H.; Heiney, P. A.: Maliszewskyj, N. C. Liq. Cryst. 1995, 19, 759. (i) Percec, V.; Schlueter, D.; Kwon, Y. K.; Blackwell, J.; Möller, M.; Slangen, P. J. Macromolecules 1995, 28, 8807. (j) Reference 27. (k) Pegenau, A.; Cheng, X. H.; Tschierske, C.; Göring, P.; Diele, S. New J. Chem. 1999, 23, 465. (l) Cheng, X. H.; Diele, S.; Tschierske, C. Angew. Chem., Int. Ed. Engl. 2000, 39, 592.
50. Examples for the stabilization of liquid crystalline phases by perfluorinated chains: (a) Viney, C.; Twieg, R, J.; Russell, T. P.; Depero, L. E. Liq. Cryst. 1989, 5, 1783. (b) Doi, T.; Sakurai, Y.; Tamatani, A.; Takenaka, S.; Kusabashi, S.; Nishihata, Y.; Terauchi, H. J. Mater. Chem. 1991, 1, 169. (c) Nguyen, H. T.; Sigaud, G.; Achard, M. F.; Hardouin, F.; Twieg, R. J.; Betterton, K. Liq. Cryst. 1991, 10, 389. (d) Pensec, S.; Tournilhac, F.-G.; Bassoul, P. J. Phys. II Fr. 1996, 6, 1597. (e) Arehart, S. V.; Pugh, C. J. Am. Chem. Soc. 1997, 119, 3027. (f) Takenaka, S. J. Chem. Soc., Chem. Commun. 1992, 1748. (g) Johansson, G.; Percec, V.; Ungar, G.; Smith, K. Chem. Mater. 1997, 9, 164. (h) Dahn, U.; Erdelen, C.; Ringsdorf, H.; Festag, R.; Wendorff, J. H.; Heiney, P. A.: Maliszewskyj, N. C. Liq. Cryst. 1995, 19, 759. (i) Percec, V.; Schlueter, D.; Kwon, Y. K.; Blackwell, J.; Möller, M.; Slangen, P. J. Macromolecules 1995, 28, 8807. (j) Reference 27. (k) Pegenau, A.; Cheng, X. H.; Tschierske, C.; Göring, P.; Diele, S. New J. Chem. 1999, 23, 465. (l) Cheng, X. H.; Diele, S.; Tschierske, C. Angew. Chem., Int. Ed. Engl. 2000, 39, 592.
51. Examples for the stabilization of liquid crystalline phases by perfluorinated chains: (a) Viney, C.; Twieg, R, J.; Russell, T. P.; Depero, L. E. Liq. Cryst. 1989, 5, 1783. (b) Doi, T.; Sakurai, Y.; Tamatani, A.; Takenaka, S.; Kusabashi, S.; Nishihata, Y.; Terauchi, H. J. Mater. Chem. 1991, 1, 169. (c) Nguyen, H. T.; Sigaud, G.; Achard, M. F.; Hardouin, F.; Twieg, R. J.; Betterton, K. Liq. Cryst. 1991, 10, 389. (d) Pensec, S.; Tournilhac, F.-G.; Bassoul, P. J. Phys. II Fr. 1996, 6, 1597. (e) Arehart, S. V.; Pugh, C. J. Am. Chem. Soc. 1997, 119, 3027. (f) Takenaka, S. J. Chem. Soc., Chem. Commun. 1992, 1748. (g) Johansson, G.; Percec, V.; Ungar, G.; Smith, K. Chem. Mater. 1997, 9, 164. (h) Dahn, U.; Erdelen, C.; Ringsdorf, H.; Festag, R.; Wendorff, J. H.; Heiney, P. A.: Maliszewskyj, N. C. Liq. Cryst. 1995, 19, 759. (i) Percec, V.; Schlueter, D.; Kwon, Y. K.; Blackwell, J.; Möller, M.; Slangen, P. J. Macromolecules 1995, 28, 8807. (j) Reference 27. (k) Pegenau, A.; Cheng, X. H.; Tschierske, C.; Göring, P.; Diele, S. New J. Chem. 1999, 23, 465. (l) Cheng, X. H.; Diele, S.; Tschierske, C. Angew. Chem., Int. Ed. Engl. 2000, 39, 592.
52. Examples for the stabilization of liquid crystalline phases by perfluorinated chains: (a) Viney, C.; Twieg, R, J.; Russell, T. P.; Depero, L. E. Liq. Cryst. 1989, 5, 1783. (b) Doi, T.; Sakurai, Y.; Tamatani, A.; Takenaka, S.; Kusabashi, S.; Nishihata, Y.; Terauchi, H. J. Mater. Chem. 1991, 1, 169. (c) Nguyen, H. T.; Sigaud, G.; Achard, M. F.; Hardouin, F.; Twieg, R. J.; Betterton, K. Liq. Cryst. 1991, 10, 389. (d) Pensec, S.; Tournilhac, F.-G.; Bassoul, P. J. Phys. II Fr. 1996, 6, 1597. (e) Arehart, S. V.; Pugh, C. J. Am. Chem. Soc. 1997, 119, 3027. (f) Takenaka, S. J. Chem. Soc., Chem. Commun. 1992, 1748. (g) Johansson, G.; Percec, V.; Ungar, G.; Smith, K. Chem. Mater. 1997, 9, 164. (h) Dahn, U.; Erdelen, C.; Ringsdorf, H.; Festag, R.; Wendorff, J. H.; Heiney, P. A.: Maliszewskyj, N. C. Liq. Cryst. 1995, 19, 759. (i) Percec, V.; Schlueter, D.; Kwon, Y. K.; Blackwell, J.; Möller, M.; Slangen, P. J. Macromolecules 1995, 28, 8807. (j) Reference 27. (k) Pegenau, A.; Cheng, X. H.; Tschierske, C.; Göring, P.; Diele, S. New J. Chem. 1999, 23, 465. (l) Cheng, X. H.; Diele, S.; Tschierske, C. Angew. Chem., Int. Ed. Engl. 2000, 39, 592.
53. Examples for the stabilization of liquid crystalline phases by perfluorinated chains: (a) Viney, C.; Twieg, R, J.; Russell, T. P.; Depero, L. E. Liq. Cryst. 1989, 5, 1783. (b) Doi, T.; Sakurai, Y.; Tamatani, A.; Takenaka, S.; Kusabashi, S.; Nishihata, Y.; Terauchi, H. J. Mater. Chem. 1991, 1, 169. (c) Nguyen, H. T.; Sigaud, G.; Achard, M. F.; Hardouin, F.; Twieg, R. J.; Betterton, K. Liq. Cryst. 1991, 10, 389. (d) Pensec, S.; Tournilhac, F.-G.; Bassoul, P. J. Phys. II Fr. 1996, 6, 1597. (e) Arehart, S. V.; Pugh, C. J. Am. Chem. Soc. 1997, 119, 3027. (f) Takenaka, S. J. Chem. Soc., Chem. Commun. 1992, 1748. (g) Johansson, G.; Percec, V.; Ungar, G.; Smith, K. Chem. Mater. 1997, 9, 164. (h) Dahn, U.; Erdelen, C.; Ringsdorf, H.; Festag, R.; Wendorff, J. H.; Heiney, P. A.: Maliszewskyj, N. C. Liq. Cryst. 1995, 19, 759. (i) Percec, V.; Schlueter, D.; Kwon, Y. K.; Blackwell, J.; Möller, M.; Slangen, P. J. Macromolecules 1995, 28, 8807. (j) Reference 27. (k) Pegenau, A.; Cheng, X. H.; Tschierske, C.; Göring, P.; Diele, S. New J. Chem. 1999, 23, 465. (l) Cheng, X. H.; Diele, S.; Tschierske, C. Angew. Chem., Int. Ed. Engl. 2000, 39, 592.
54. Examples for the stabilization of liquid crystalline phases by perfluorinated chains: (a) Viney, C.; Twieg, R, J.; Russell, T. P.; Depero, L. E. Liq. Cryst. 1989, 5, 1783. (b) Doi, T.; Sakurai, Y.; Tamatani, A.; Takenaka, S.; Kusabashi, S.; Nishihata, Y.; Terauchi, H. J. Mater. Chem. 1991, 1, 169. (c) Nguyen, H. T.; Sigaud, G.; Achard, M. F.; Hardouin, F.; Twieg, R. J.; Betterton, K. Liq. Cryst. 1991, 10, 389. (d) Pensec, S.; Tournilhac, F.-G.; Bassoul, P. J. Phys. II Fr. 1996, 6, 1597. (e) Arehart, S. V.; Pugh, C. J. Am. Chem. Soc. 1997, 119, 3027. (f) Takenaka, S. J. Chem. Soc., Chem. Commun. 1992, 1748. (g) Johansson, G.; Percec, V.; Ungar, G.; Smith, K. Chem. Mater. 1997, 9, 164. (h) Dahn, U.; Erdelen, C.; Ringsdorf, H.; Festag, R.; Wendorff, J. H.; Heiney, P. A.: Maliszewskyj, N. C. Liq. Cryst. 1995, 19, 759. (i) Percec, V.; Schlueter, D.; Kwon, Y. K.; Blackwell, J.; Möller, M.; Slangen, P. J. Macromolecules 1995, 28, 8807. (j) Reference 27. (k) Pegenau, A.; Cheng, X. H.; Tschierske, C.; Göring, P.; Diele, S. New J. Chem. 1999, 23, 465. (l) Cheng, X. H.; Diele, S.; Tschierske, C. Angew. Chem., Int. Ed. Engl. 2000, 39, 592.
55. Examples for the stabilization of liquid crystalline phases by perfluorinated chains: (a) Viney, C.; Twieg, R, J.; Russell, T. P.; Depero, L. E. Liq. Cryst. 1989, 5, 1783. (b) Doi, T.; Sakurai, Y.; Tamatani, A.; Takenaka, S.; Kusabashi, S.; Nishihata, Y.; Terauchi, H. J. Mater. Chem. 1991, 1, 169. (c) Nguyen, H. T.; Sigaud, G.; Achard, M. F.; Hardouin, F.; Twieg, R. J.; Betterton, K. Liq. Cryst. 1991, 10, 389. (d) Pensec, S.; Tournilhac, F.-G.; Bassoul, P. J. Phys. II Fr. 1996, 6, 1597. (e) Arehart, S. V.; Pugh, C. J. Am. Chem. Soc. 1997, 119, 3027. (f) Takenaka, S. J. Chem. Soc., Chem. Commun. 1992, 1748. (g) Johansson, G.; Percec, V.; Ungar, G.; Smith, K. Chem. Mater. 1997, 9, 164. (h) Dahn, U.; Erdelen, C.; Ringsdorf, H.; Festag, R.; Wendorff, J. H.; Heiney, P. A.: Maliszewskyj, N. C. Liq. Cryst. 1995, 19, 759. (i) Percec, V.; Schlueter, D.; Kwon, Y. K.; Blackwell, J.; Möller, M.; Slangen, P. J. Macromolecules 1995, 28, 8807. (j) Reference 27. (k) Pegenau, A.; Cheng, X. H.; Tschierske, C.; Göring, P.; Diele, S. New J. Chem. 1999, 23, 465. (l) Cheng, X. H.; Diele, S.; Tschierske, C. Angew. Chem., Int. Ed. Engl. 2000, 39, 592.
56. Examples for the stabilization of liquid crystalline phases by perfluorinated chains: (a) Viney, C.; Twieg, R, J.; Russell, T. P.; Depero, L. E. Liq. Cryst. 1989, 5, 1783. (b) Doi, T.; Sakurai, Y.; Tamatani, A.; Takenaka, S.; Kusabashi, S.; Nishihata, Y.; Terauchi, H. J. Mater. Chem. 1991, 1, 169. (c) Nguyen, H. T.; Sigaud, G.; Achard, M. F.; Hardouin, F.; Twieg, R. J.; Betterton, K. Liq. Cryst. 1991, 10, 389. (d) Pensec, S.; Tournilhac, F.-G.; Bassoul, P. J. Phys. II Fr. 1996, 6, 1597. (e) Arehart, S. V.; Pugh, C. J. Am. Chem. Soc. 1997, 119, 3027. (f) Takenaka, S. J. Chem. Soc., Chem. Commun. 1992, 1748. (g) Johansson, G.; Percec, V.; Ungar, G.; Smith, K. Chem. Mater. 1997, 9, 164. (h) Dahn, U.; Erdelen, C.; Ringsdorf, H.; Festag, R.; Wendorff, J. H.; Heiney, P. A.: Maliszewskyj, N. C. Liq. Cryst. 1995, 19, 759. (i) Percec, V.; Schlueter, D.; Kwon, Y. K.; Blackwell, J.; Möller, M.; Slangen, P. J. Macromolecules 1995, 28, 8807. (j) Reference 27. (k) Pegenau, A.; Cheng, X. H.; Tschierske, C.; Göring, P.; Diele, S. New J. Chem. 1999, 23, 465. (l) Cheng, X. H.; Diele, S.; Tschierske, C. Angew. Chem., Int. Ed. Engl. 2000, 39, 592.
57. Examples for the stabilization of liquid crystalline phases by perfluorinated chains: (a) Viney, C.; Twieg, R, J.; Russell, T. P.; Depero, L. E. Liq. Cryst. 1989, 5, 1783. (b) Doi, T.; Sakurai, Y.; Tamatani, A.; Takenaka, S.; Kusabashi, S.; Nishihata, Y.; Terauchi, H. J. Mater. Chem. 1991, 1, 169. (c) Nguyen, H. T.; Sigaud, G.; Achard, M. F.; Hardouin, F.; Twieg, R. J.; Betterton, K. Liq. Cryst. 1991, 10, 389. (d) Pensec, S.; Tournilhac, F.-G.; Bassoul, P. J. Phys. II Fr. 1996, 6, 1597. (e) Arehart, S. V.; Pugh, C. J. Am. Chem. Soc. 1997, 119, 3027. (f) Takenaka, S. J. Chem. Soc., Chem. Commun. 1992, 1748. (g) Johansson, G.; Percec, V.; Ungar, G.; Smith, K. Chem. Mater. 1997, 9, 164. (h) Dahn, U.; Erdelen, C.; Ringsdorf, H.; Festag, R.; Wendorff, J. H.; Heiney, P. A.: Maliszewskyj, N. C. Liq. Cryst. 1995, 19, 759. (i) Percec, V.; Schlueter, D.; Kwon, Y. K.; Blackwell, J.; Möller, M.; Slangen, P. J. Macromolecules 1995, 28, 8807. (j) Reference 27. (k) Pegenau, A.; Cheng, X. H.; Tschierske, C.; Göring, P.; Diele, S. New J. Chem. 1999, 23, 465. (l) Cheng, X. H.; Diele, S.; Tschierske, C. Angew. Chem., Int. Ed. Engl. 2000, 39, 592.
58. Examples for the stabilization of liquid crystalline phases by perfluorinated chains: (a) Viney, C.; Twieg, R, J.; Russell, T. P.; Depero, L. E. Liq. Cryst. 1989, 5, 1783. (b) Doi, T.; Sakurai, Y.; Tamatani, A.; Takenaka, S.; Kusabashi, S.; Nishihata, Y.; Terauchi, H. J. Mater. Chem. 1991, 1, 169. (c) Nguyen, H. T.; Sigaud, G.; Achard, M. F.; Hardouin, F.; Twieg, R. J.; Betterton, K. Liq. Cryst. 1991, 10, 389. (d) Pensec, S.; Tournilhac, F.-G.; Bassoul, P. J. Phys. II Fr. 1996, 6, 1597. (e) Arehart, S. V.; Pugh, C. J. Am. Chem. Soc. 1997, 119, 3027. (f) Takenaka, S. J. Chem. Soc., Chem. Commun. 1992, 1748. (g) Johansson, G.; Percec, V.; Ungar, G.; Smith, K. Chem. Mater. 1997, 9, 164. (h) Dahn, U.; Erdelen, C.; Ringsdorf, H.; Festag, R.; Wendorff, J. H.; Heiney, P. A.: Maliszewskyj, N. C. Liq. Cryst. 1995, 19, 759. (i) Percec, V.; Schlueter, D.; Kwon, Y. K.; Blackwell, J.; Möller, M.; Slangen, P. J. Macromolecules 1995, 28, 8807. (j) Reference 27. (k) Pegenau, A.; Cheng, X. H.; Tschierske, C.; Göring, P.; Diele, S. New J. Chem. 1999, 23, 465. (l) Cheng, X. H.; Diele, S.; Tschierske, C. Angew. Chem., Int. Ed. Engl. 2000, 39, 592.
59. X-ray investigations indicate a layer distance corresponding to a single-layer arrangement, i.e. no hint on the segregation of the fluorinated and the nonfluorinated chains could be observed, which should lead to a bilayer arrangement.
60. Only one sharp current peak can be detected by applying a peak to peak voltage below 92 V which would suggest a ferroelectric switching (see ref 20). On increasing the peak-to peak voltage a broad second peak occurs which becomes sharper on increasing the triangular voltage.
61. Pelzl, G.; Diele, S.; Grande, S.; Jakli, A.; Lischka, C.; Kresse, H.; Schmalfuss, H.; Wirth, I. Liq. Cryst. 1999, 26, 401.