Browse > Article
http://dx.doi.org/10.14478/ace.2011.22.4.358

Thermotropic Liquid Crystalline Properties of α,ω-Bis(4-cyanoazobenzene-4'-oxy)alkanes  

Jeong, Seung Yong (Center for Photofunctional Energy Materials, Dankook University)
Kim, Hyo Gap (Center for Photofunctional Energy Materials, Dankook University)
Ma, Yung Dae (Center for Photofunctional Energy Materials, Dankook University)
Publication Information
Applied Chemistry for Engineering / v.22, no.4, 2011 , pp. 358-366 More about this Journal
Abstract
A homologous series of linear liquid crystal dimers, the ${\alpha},{\omega}$-bis(4-cyano-azobenzene-4'-oxy)alkanes (CATWETn, where n, the number of methylene units in the spacer, is 2~10) were synthesized, and their thermotropic liquid crystalline phase behavior were investigated. The CATWETn with n of 3 and 6 exhibited monotropic nematic phases, whereas other derivatives showed enantiotropic nematic phases. The nematic-isotropic transition temperatures of the dimers and their entropy variation at the phase transition showed a large odd-even effect as a function of n. This phase transition behavior was rationalized in terms of the change in the average shape of the spacer on varying the parity of the spacer. The thermal stability and degree of order in the nematic phase and the magnitude of the odd-even effect of CATWETn were similar to those for the methoxy-, nitro-, and pentyl-substituted dimers, while they were significantly different from those for the monomesogenic compounds, 1-{4-(4'-cyanophenylazo)phenoxy}alkylbromides and the side-chain liquid-crystalline polymers, the poly[1-{4-(4'-cyanophenylazo)phenoxyalkyloxy}ethylene]s. The results were discussed in terms of 'virtual trimer model' by Imrie.
Keywords
cyanoazobenzene; symmetric dimer; ether linkage; nematic phase; odd-even effect;
Citations & Related Records
Times Cited By KSCI : 3  (Citation Analysis)
Times Cited By SCOPUS : 0
연도 인용수 순위
1 K. Zygadlo, D. Dardas, K. Nowicka, J. Hofmann, and Z, Galewski, Mol. Cryst. Liq. Cryst., 509, 283 (2009).
2 B.-K. So, H.-J. Kim, S.-M. Lee, H.-H. Song, and J.-H. Park, Dyes and Pigments, 70, 38 (2006).   DOI   ScienceOn
3 B. Bai, H. Wang, H. Xin, J. Shi, B. Long, and M. Li, J. Phys. Org. Chem., 20, 589 (2007).   DOI   ScienceOn
4 B. Bai, H. Wang, S. Qu, F. Li, Z. Yu, B. Long, and M. Li, Liq. Cryst., 35, 793 (2008).   DOI   ScienceOn
5 A. A. Salisu, M. Z. Ab. Rahman, S. Silong, M. Bin Ahmad, and M. R. Lutfor, Mol. Cryst. Liq. Cryst., 509, 134 (2009).
6 K. Ichimura, Chem. Rev., 100, 1847 (2000).   DOI   ScienceOn
7 J.-C. Dubois, P. L. Barny, M. Mauzac, and C. Noel, Handbook of Liquid Crystals, eds. D. Demus, J. Goodby, G. W. Gray, H.-W. Spiess, and V. Vill, 3, 207, Wiley-VCH, Weinheim-New York (1998).
8 V. Shibaev, A. Bobrovsky, and N. Boiko, Prog. Polym. Sci., 28, 729 (2003).   DOI   ScienceOn
9 V. Percec and C. Pugh, Side Chain Liquid Crystal Polymers, ed. C. B. McArdle, 30, Chapman and Hall, New York (1989).
10 A. Natansohn and P. Rochon, Chem. Rev., 102, 4139 (2002).   DOI   ScienceOn
11 C. T. Imrie, F. E. Karasz, and G. S. Attard, Macromoleules, 26, 545 (1993).   DOI
12 M. Li, E. Zhou, J. Xu, and X. Chen, J. Appl. Polym. Sci., 60, 2185 (1996).   DOI   ScienceOn
13 M. Ratloh, J. Stumpe, L. Stachanov, S. Kostromin, and V. Shibaev, Mol. Cryst. Liq. Cryst., 352, 149 (2000).   DOI   ScienceOn
14 A. A. Craig, I. Winchester, P. C. Madden, P. Larcey, I. W. Hamley, and C. T. Imrie, Polymer, 39, 1197 (1998).   DOI   ScienceOn
15 J-H. Liu and C.-D. Hsieh, J. Appl. Polym. Sci., 99, 2443 (2006).   DOI   ScienceOn
16 X. Li, R. Wen, Y. Zhang, L. Zhu, B. Zhang, and H. Zhang, J. Mater. Chem., 19, 236 (2009).   DOI   ScienceOn
17 Z. Zheng, J. Xu, Y. Sun, J. Zhou, B. Chen, Q. Zhang, and K. Wang, J. Polym. Sci. Part A: Polm. Chem., 44, 3210 (2006).   DOI   ScienceOn
18 C. Cojocariu and P. Rochon, Macromolecules, 38, 9526 (2005).   DOI   ScienceOn
19 S. Freiberg, F. Langugne-Labarthet, P. Rochon, and A. Natansohn, Macromoleules, 36, 2680 (2003).   DOI   ScienceOn
20 S.-Y. Jeong and Y.-D. Ma, Polymer (Korea), 32, 489 (2008).
21 S.-Y. Jeong and Y.-D. Ma, J. Korean Ind. Eng. Chem., 19, 504 (2008).
22 S.-Y. Jeong, D.-J. Hwang, and Y.-D. Ma, Appl. Chem. Eng., 21, 230 (2010).
23 S.-Y. Jeong, J.-Y. Lee, and Y.-D. Ma, Polymer (Korea), 33, 297 (2009).
24 U. Hrozhyk, S. Serak, N. Tabiryan, and T. J. Bunning, Mol. Cryst. Liq. Cryst., 454, 235 (2006).
25 G. W. Gray, Liquid Crystals and Plastic Crystals, eds. G. W. Gray and P. A. Winsor, 1, 103, Ellis Harwood, Chichester, London (1974).
26 S.-Y. Jeong and Y.-D. Ma, Polymer (Korea), 30, 35 (2006).
27 G. W. Gray, The Molecular Physics of Liquid Crystals, eds. G. R. Luckhurst and G. W. Gray, 1, Academic Press, New York (1979).
28 Ya. S. Freidzon and V. P. Shibaev, Liquid-Crystal Polymers, ed. N. A. Plate, 251, Plenum Press, New York and London (1993).
29 C. T. Imrie, F. E. Karasz, and G. S. Attard, Macromoleules, 26, 3803 (1993).   DOI   ScienceOn
30 T. Tanaka, T. Fukuda, J. Watanabe, and T. Miyamoto, Macromolecules, 28, 3394 (1995).   DOI   ScienceOn
31 W. Maier and A. Saupe, Z. Naturf, 14a, 882 (1959)
32 W, Maier and A. Saupe, Z. Naturf, 15a, 287 (1960).
33 L. Onsager, Ann. N. Y. Acad. Sci., 51, 627 (1949).   DOI   ScienceOn
34 G. Vertogen and W. H. de Jeu, Thermotropic Liquid Crystals, Fundamentals, 245, Springer-Verlag, Berlin Heidelberg (1988).
35 S. Chandrasekhar, Liquid Crystals, 17, Cambridge University Press (1992).
36 W. H. de Jeu, J. van der Veen, and W. J. A. Goosens, Solid State Commun., 12, 405 (1973).   DOI   ScienceOn
37 V. Percec, A. D. Asandei, D. H. Hill, and D. Crawford, Macromoleules, 32, 2597 (1999).   DOI   ScienceOn
38 A. A. Craig and C. T. Imrie, J. Mater. Chem., 4, 1705 (1994).   DOI   ScienceOn
39 F. Dowell and D. E. Martie, J. Chem. Phys., 68, 1094 (1979).
40 P. A. Henderson, O. Niemeyer, and C. T. Imrie, Liq. Cryst., 28, 463 (2001).   DOI   ScienceOn
41 A. E. Blatch, I. D. Fletcher, and G. R. Luckhurst, J. Mater. Chem., 7, 9 (1997).   DOI   ScienceOn
42 J. I. Jin, Mol. Cryst. Liq. Cryst., 267, 249 (1995).   DOI   ScienceOn
43 Y. Yu and T. Ikeda, J. Photochem. Photobiol. C: Photochem. Rev., 5, 247 (2004).   DOI   ScienceOn
44 C. J. Barrett, J. Mamiya, K. G. Yager, and T. Ikeda, Soft Matter, 3, 1249 (2007).   DOI   ScienceOn
45 T. Ikeda, J. Mamiya, and Y. Yu, Angew. Chem. Int. Ed., 46, 506 (2007).   DOI   ScienceOn
46 T. Yoshino, M. Kondo, J. Mamiya, M. Kinoshita, Y. Yu, and T. Ikeda, Adv. Mater., 22, 1361 (2010).   DOI   ScienceOn
47 N. Tamaoki and T. Kamei, J. Photochem. Photobiol. C: Photochem. Rev., 11, 47 (2010).   DOI   ScienceOn
48 C. T. Imrie and G. R. Luckhurst, Handbook of Liquid Crystals, eds. D. Demus, G. Goodby, G. W. Gray, H.-W. Spiess, and V. Vill, 2B, 801, Wiley-VCH, Weinheim-New York (1998).
49 C. T. Imrie and P. A. Henderson, Chem. Soc. Rev., 36, 2096 (2007).   DOI   ScienceOn
50 C. T. Imrie, P. A. Henderson, and G.-Y. Yeap, Liq. Cryst., 36, 755 (2009).   DOI   ScienceOn
51 T. Donaldson, H. Staesche, Z. B. Lu, P. A. Henderson, M. F. Achard, and C. T. Imrie, Liq. Cryst., 37, 1097 (2010).   DOI   ScienceOn
52 S.-Y. Jeong, H.-G. Kim, H.-S. Jung, and Y.-D. Ma, Chemical Materials (Dankook University), 6, 27 (2009).
53 P. A. Henderson, A. G. Cook, and C. T. Imrie, Liq. Cryst., 31, 1427 (2004).   DOI   ScienceOn
54 S. K. Prasad, K. L. Sandhya, G. G. Nair, U. S. Hiremath, and C. V. Yelamaggad, J. Appl. Phys., 92, 838 (2002).   DOI   ScienceOn
55 G. S. Attard, S. Garnett, C. G. Hickman, C. T. Imrie, and L. Taylor, Liq. Cryst., 7, 495 (1990).   DOI   ScienceOn
56 A. E. Blatch and G. R. Luckhurst, Liq. Cryst., 27, 775 (2000).   DOI   ScienceOn
57 V. A. Mallia and N. Tamaoki, J. Mater. Chem., 13, 219 (2003).   DOI   ScienceOn
58 T. Niori, S. Adachi, and J. Watanabe, Liq. Cryst., 19, 139 (1995).   DOI
59 M. Moriyama and N. Tamaoki, Chem. Lett., 1142 (2001).
60 V. A. Mallia and N. Tamaoki, Chem. Mater., 15, 3237 (2003).   DOI   ScienceOn
61 N. Tamaoki, Y. Aoki, M. Moriyama, and M. Kidowaki, Chem. Mater., 15, 719 (2003).   DOI   ScienceOn
62 S. Kumaresan, V. A. Mallia, Y. Kida, and N. Tamaoki, J. Mater. Res., 20, 3431 (2005).   DOI   ScienceOn
63 C. V. Yelamaggad, G. Shanker, U. S. Hiremath, and S. Krishna Prasad, J. Mater. Chem., 18, 2927 (2008).   DOI   ScienceOn
64 C. Wu, Mater. Lett., 61, 1380 (2007).   DOI   ScienceOn
65 S.-W. Cha, J.-I. Jin, M. Laguerre, M. F. Achard, and F. Hardouin, Liq. Cryst., 26, 1325 (1999).   DOI   ScienceOn
66 J.-W. Lee, Y. Park, J.-I. Jin, M. F. Achard, and F. Hardouin, J. Mater. Chem., 13, 1367 (2003).   DOI   ScienceOn
67 K.-N. Kim, E.-D. Do, Y.-W. Kwon, and J.-I. Jin, Liq. Cryst., 32, 229 (2005).   DOI   ScienceOn
68 W.-K. Lee, K.-N. Kim, M. F. Achard, and J.-I. Jin, J. Mater. Chem., 16, 2289 (2006).   DOI   ScienceOn