Liquid crystalline imidazolium salts bearing 5-phenylpyrimidine: Dependence of mesomorphic properties on spacer lengths, terminal N-alkyl group and counterions

Liquid Crystals

Volumn 38, Issue 11-12, 2011, Pages 1515-1529

  Starkulla, Gundula ^a   Kaller, Martin ^a   Frey, Wolfgang ^a   Axenov, Kirill V ^a   Laschat, Sabine ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

Author keywords

Calamitic; Imidazolium salts; Ionic liquid crystals; Phenylpyrimidines

Indexed keywords

EID: 84855677089     PISSN: 02678292     EISSN: 13665855     Source Type: Journal    
DOI: 10.1080/02678292.2011.614699     Document Type: Article

References (72)

1. Binnemans, K., 2005. Chem. Rev., 105:4148–4204.
2. Kato, T., Mizoshita, N., and Kishimoto, K., 2006. Angew. Chem. Angew. Chem., Int. Ed., 118:44–74. 2006, 45, 38–68
3. Axenov, K.V, and Laschat, S., 2011. Materials, 4:206–259.
4. Yoshio, M., Mukai, T., Kanie, K., Yoshizawa, M., Ohno, H., and Kato, T., 2002. Adv. Mater, 14:351–354.
5. Yoshio, M., Mukai, T., Ohno, H., and Kato, T., 2004. J. Am. Chem. Soc, 126:994–995.
6. Yoshio, M., Kagata, T., Hoshino, K., Mukai, T., Ohno, H., and Kato, T., 2006. J. Am. Chem. Soc., 128:5570–5577.
7. Shimura, H., Yoshio, M., Hoshino, K., Mukai, T., Ohno, H., and Kato, T., 2008. J. Am. Chem. Soc, 130:1759–1765.
8. Kato, T., 2010. Angew. Chem. Angew. Chem., Int. Ed., 122:8019–8021. 2010, 49, 7847–7848
9. Yazaki, S., Funahashi, M., Kagimoto, J., Ohno, H., and Kato, T., 2010. J. Am. Chem. Soc, 132:7702–7708.
10. Gorlov, M., and Kloo, L., 2008. Dalton Trans.,:2655–2666.
11. Zakeeruddin, S.M., and Grätzel, M., 2009. Adv. Funct. Mater, 19:2187–2202.
12. Hagfeldt, A., Boschloo, G., Sun, L., Kloo, L., and Pettersson, H., 2010. Chem. Rev, 110:6595–6663.
13. Binnemans, K., 2009. J. Mater. Chem, 19:448–453. and references therein
14. Lee, C.K, Huang, H.W., and Lin, I.J.B., 2000. Chem. Commun,:1911–1912.
15. Taubert, A., 2004. Angew. Chem. Angew. Chem., Int. Ed., 116:5494–5496. 2004, 43, 5380–5382
16. Taubert, A., Arbell, I., Mecke, A., and Graf, P., 2006. Gold Bull, 39:205–211.
17. Dobbs, W., Suisse, J.-M., Douce, L., and Welter, R., 2006. Angew. Chem. Angew. Chem., Int. Ed., 118:4285–4288. 2006, 45, 4179–4182
18. Taubert, A., and Li, Z., 2007. Dalton Trans,:723–727.
19. Taubert, A., Palivan, C., Casse, O., Gozzo, F., and Schmitt, B., 2007. J. Phys. Chem. C, 111:4077–4082.
20. Wang, Q.T., Wang, X.B., Lou, W.J., and Hao, J.C., 2009. ChemPhysChem, 10:3201–3203.
21. Plechkova, N.V., and Seddon, K.R., 2008. Chem. Soc. Rev, 37:123–150. and references therein
22. Welton, T., 1999. Chem Rev, 99:2071–2083.
23. Wasserscheid, P., and Keim, W., 2000. Angew. Chem. Angew. Chem., Int. Ed., 118:4285–4288. 2000, 39, 3772–3789
24. Hallett, J.P., and Welton, T., 2011. Chem. Rev., 111:3508–3576.
25. Deshmukh, R.R., Rajagopal, R., and Srinivasan, K.V., 2001. Chem. Commun,:1544–1545.
26. Xiao, J.-C., Twamley, B., and Shreeve, J.M., 2004. Org. Lett, 6:3845–3847.
27. Lin, I.J.B., and Vasam, C.S., 2005. J. Organomet. Chem, 690:3498–3512. and references therein
28. Rogers, R.D., and Seddon, K.R., 2003. Science, 302:792–793.
29. Maase, M., 2004. Chem. Unserer Z., 38:434–436.
30. Schubert, T.J.S., 2005. Nachr. Chem, 53:1222–1226.
31. Kosan, B., Michels, C., and Meister, F., 2008. Cellulose, 15:59–66.
32. Hermanutz, F., Gähr, F., Uerdingen, E., Meister, F., and Kosan, B., 2008. Macromol. Symp, 262:23–27.
33. Romanenko, I.V., and Sheinkman, A.K., 1980. Khim. Heterocycl. Soed, 11:1567–1568.
34. Katritzky, A.R., 1980. Tetrahedron, 36:679–699.
35. Kohnen, G., Tosoni, M., Tussetschläger, S., Baro, A., and Laschat, S., 2009. Eur. J. Org. Chem., 32:5601–5609.
36. Demus, D., Goodby, J., Gray, G.W., Spiess, H.-W., and Vill, V., 1998. Handbook of Liquid Crystals, 1–4. New York:Wiley-VCH:Weinheim, Germany. NY, USA; Chichester, UK; Brisbane, Australia; Singapore, and Toronto, Canada
37. Gray, G.W., Harrison, K.J., and Nash, J.A., 1973. Electron. Lett, 9:130–131.
38. Sage, I., 1981. Microelectron. J, 12:30–32.
39. Kouwer, P.H.J., and Swager, T.M., 2007. J. Am. Chem. Soc., 129:14042–14052.
40. Pal, S.K., and Kumar, S., 2006. Tetrahedron Lett, 47:8993–8997.
41. Goossens, K., Nockemann, P., Driesen, K., Goderis, B., Görller-Walrand, C., van Hecke, K., van Meervelt, L., Pouzet, E., Binnemans, K., and Cardinaels, T., 2008. Chem. Mater., 20:157–168.
42. Yoshizawa, H., Mihara, T., and Koide, N. 2004. Mol. Cryst. Liq. Cryst, 423:61–72.
43. Hartley, C.S., Kapernaum, N., Roberts, J.C., Giesselmann, F., and Lemieux, R.P., 2006. J. Mater. Chem., 16:2329–2337.
44. Kidowaki, M., Moriyama, M., Wada, M., and Tamaoki, N., 2003. J. Phys. Chem. B, 107:12054–12061.
45. Sharma, N.K., Müller, I., Wingen, R., Dübal, H.R., Escher, C., and Ohlendorf, D., 1987. Mol. Cryst. Liq. Cryst., 151:225–232.
46. Barone, V., Commisso, L., Lelj, F., and Russo, N., 1985. Tetrahedron, 41:1915–1918.
47. Pecheanu, R., and Cann, N.M., 2010. Phys. Rev. E:Stat, Nonlinear, Soft Matter Phys, 81:041704-1–17.
48. Petrov, V.F., 2006. Mol. Cryst. Liq. Cryst, 457:121–149.
49. Petrov, V.F., 2002. Liq. Cryst, 29:805–835.
50. Sugita, S.-I., Takeno, H., and Teraji, T., 1991. Mol. Cryst. Liq. Cryst, 206:139–146.
51. Sugita, S.-I., Toda, S., Yoshiyasu, T., and Teraji, T., 1994. Mol. Cryst. Liq. Cryst, 239:113–122.
52. Bremer, M., 1995. Adv. Mater, 7:803–807.
53. Reiffenrath, V., Bremer, M., and Junge, M., 1994. DE 19944410606 (B4), 6 October
54. Neumann, B., Hegmann, T., Wagner, C., Ashton, P.R., Wolf, R., and Tschierske, C., 2003. J. Mater. Chem, 13:778–784.
55. Li, L., Jones, C.D., Magolan, J., and Lemieux, R.P., 2007. J. Mater. Chem, 17:2313–2318.
56. deVries, A. 1979. J. Chem. Phys., 71:25–31.
57. Radcliffe, M.D., Brostrom, M.L., Epstein, K.A., Rappaport, A.G., Thomas, B.N., Shao, R., and Clark, N.A., 1999. Liq. Cryst, 26:789–794.
58. Lagerwall, J.P.F., Giesselmann, F., and Radcliffe, M.D., 2002. Phys. Rev. E:Stat. Nonlinear, Soft Matter Phys, 66:031703-1–11.
59. Spector, M.S., Heiney, P.A., Naciri, J., Weslowski, B.T., Holt, D.B., and Shashidhar, R., 2000. Phys. Rev. E:Stat. Nonlinear, Soft Matter Phys, 61:1579–1584.
60. Naciri, J., Carboni, C., and George, A.K., 2003. Liq. Cryst, 30:219–225.
61. Panarina, O.E., Panarin, Y.P., Vij, J.K., Spector, M.S., and Shashidhar, R., 2003. Phys. Rev. E:Stat. Nonlinear, Soft Matter Phys, 67:051709-1–6.
62. Hayashi, N., Kato, T., Fukuda, A., Vij, J.K., Panarin, Y.P., Naciri, J., Shashidhar, R., Kawada, S., and Kondoh, S., 2005. Phys. Rev. E:Stat. Nonlinear, Soft Matter Phys, 71:041705-1–8.
63. Panarina, O.E., Panarin, Y.P., Antonelli, F., Vij, J.K., Reihmann, M., and Galli, G., 2006. J. Mater. Chem, 16:842–849.
64. Roberts, J.C., Kapernaum, N., Giesselmann, F., and Lemieux, R.P., 2008. J. Am. Chem. Soc, 130:13842–13843.
65. Roberts, J.C., Kapernaum, N., Song, Q., Nonnenmacher, D., Ayub, K., Giesselmann, F., and Lemieux, R.P., 2010. J. Am. Chem. Soc, 132:364–370.
66. Nonnenmacher, D., Osipov, M.A., Roberts, J.C., Lemieux, R.P., and Giesselmann, F., 2010. Phys. Rev. E:Stat. Nonliner, Soft Matter Phys, 82:031703-1–7.
67. Starkulla, G.F., Kapatsina, E., Baro, A., Giesselmann, F., Tussetschläger, S., Kaller, M., and Laschat, S., 2009. Beilstein J. Org. Chem, 5 doi:10.3762/bjoc.5.63
68. Kapatsina, E., Lordon, M., Baro, A., and Laschat, S., 2008. Synthesis,:2551–2560.
69. Holbrey, J.D., and Seddon, K.R., 1999. J. Chem. Soc., Dalton Trans,:2133–2140.
70. Dierking, I., 2003. Textures of Liquid Crystals, Wiley-VCH:Weinheim
71. Chem3D Pro 2008 software was used for molecular modelling
72. QtiPlot version 0.9.8.4 was used for Lorentz distribution