Synthesis and mesomorphic properties of rigid-core ionic liquid crystals

Journal of the American Chemical Society

Volumn 129, Issue 45, 2007, Pages 14042-14052

  Kouwer, Paul H J ^a,b   Swager, Timothy M ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

^b RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

HIGH TEMPERATURE EFFECTS; IONIC LIQUIDS; MELTING; MIXTURES; PARAMETER ESTIMATION; SUBSTITUTION REACTIONS;

IMIDAZOLIUM; ION-DOPING; MESOMORPHIC PROPERTIES;

LIQUID CRYSTALS;

IONIC LIQUID; SOLVENT;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; DIFFERENTIAL SCANNING CALORIMETRY; LIQUID CRYSTAL; MOLECULAR MODEL; POLARIZATION MICROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; SYNTHESIS; TEMPERATURE; X RAY DIFFRACTION;

CRYSTALLIZATION; IONS; LIQUID CRYSTALS; MOLECULAR STRUCTURE; PARTICLE SIZE; PHASE TRANSITION; STEREOISOMERISM; SURFACE PROPERTIES; TEMPERATURE; X-RAY DIFFRACTION;

EID: 36148956707     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja075651a     Document Type: Article

References (54)

1. For recent reviews on task-specific ionic liquids: (a) Lee, S. Chem. Commun. 2006, 1049-1063.
2. (b) Davis, J. D, Jr. Synthesis of task-specific ionic liquids. In Ionic Liquids in Synthesis: Wasserscheid, P., Welton, T., Eds.; Wiley-VCH: Berlin, 2003; pp 33-40.
3. For examples of Friedel-Crafts reactions: (a) Boon, J. A.; Levisky, J. A.; Pflug, J. L.; Wilkes, J. S. J. Org. Chem. 1986, 51, 480.
4. Esterifications: (b) Cole, A. C.; Jensen, J. L.; Ntai, I.; Tran, K. L. T.; Weaver, K. J.; Forbes, D. C.; Davis, J. H. J. Am. Chem. Soc. 2002, 124, 5962-5963.
5. (a) Fraga-Dubreuil, J.; Bazureau, J. P. Tetrahedron Lett. 2001, 42, 6097-6100.
6. (b) Miao, W.; Chan, T. H. Org. Lett. 2003, 5, 5003-5005.
7. (c) Anjaiah, S.; Chandrasekhar, S.; Gree, R. Tetrahedron Lett. 2004, 45, 569-571.
8. (a) Visser, A. E.; Swatloski, R. P.; Reichert, W. M.; Davis, J. H.; Rogers, R. D.; Mayton, R.; Sheff, S.; Wierzbicki, A. Chem. Commun. 2001, 135-136.
9. (b) Visser, A. E.; Swatloski, R. P.; Reichert, W. M.; Mayton, R.; Sheff, S.; Wierzbicki, A.; Davis, J. H.; Rogers, R. D. Environ. Sci. Technol. 2002, 36, 2523-2529.
10. (a) Gadenne, B.; Hesemann, P.; Moreau, J. J. E. Chem. Commun. 2004, 1768-1769.
11. (b) Dobbs, W.; Suisse, J.-M.; Douce, L.; Welter, R. Angew. Chem., Int. Ed. 2006, 45, 4179-4182.
12. (c) Zhu, Y. J.; Wang, W. W.; Qi, R. J.; Hu, X. L. Angew. Chem., Int. Ed. 2004, 43, 1410.
13. (d) Wang, Y.; Yang, H. J. Am. Chem. Soc. 2005, 127, 5316.
14. (a) Itoh, H.; Naka, K.; Chujo, Y. J. Am. Chem. Soc. 2004, 126, 3026-3027.
15. (b) Kim, K.-S.; Demberelnyamba, D.; Lee, H. Langmuir 2004, 20, 556-560.
16. (a) Trulove, P. C.; Mantz, R. A. Electrochemical Properties of Ionic Liquids. In Ionic Liquids in Synthesis; Wasserscheid, P., Welton, T., Eds.; Wiley-VCH: Berlin. 2003; pp 103-126.
17. (b) Ohno, H., Ed. Electrochemical Aspects of Ionic Liquids; Wiley: Hoboken, NJ, 2005.
18. (c) Buzzeo, M. C.; Evans, R. G.; Compton, R. G. ChemPhysChem. 2004, 5, 1106-1120.
19. (d) Bonhôte, P.; Dias, A.-P.; Papageorgiou, N.; Kalyanasundaram, K.; Grätzel, M. Inorg. Chem. 1996, 35, 1168-1178.
20. (e) Forsyth, S. A.; Pringle, J. M.; MacFarlane, D. R. Aust. J. Chem. 2004, 57, 113-119.
21. Zhu, Z.; Swaaer, T. M. J. Am. Chem. Soc. 2002, 124, 9670-9671.
22. (a) Long, T. M.; Swager, T. M. Adv. Mater. 2001, 13, 601-604.
23. (b) Long, T. M.; Swager, T. M. J. Am. Chem. Soc. 2002, 124, 3826-3827.
24. (c) Amemiya, K.; Shin, K. C.; Takanishi, Y.; Ishikawa, K.; Azumi, R.; Takezoe, H. J. Appl. Phys. 2004, 43, 6084-6087.
25. (a) Gray, D. H.; Gin, D. L. Chem. Mater. 1998, 10, 1827.
26. (b) Dag, Ö.; Alayoglu, S.; Tura, C.; Çelik, Ö. Chem. Mater. 2003, 15, 2711-2717.
27. (c) Yamauchi, Y.; Momma, T.; Yokoshima, T.; Kuroda, K.; Osaka, T. J. Mater. Chem. 2005, 15, 1987-1994.
28. (a) Hoshino, K.; Yoshio, M.; Mukai, T.; Kishimoto, K.; Ohno, H.; Kato, T. J. Polym. Sci., Part A: Polym. Chem. 2003, 41, 3486-3492.
29. (b) Yoshio, M.; Mukai, T.; Ohno, H.; Kato, T. J. Am. Chem. Soc. 2004, 126, 994-995.
30. (c) Yoshio, M.; Kagata, T.; Hoshino, K.; Mukai, T.; Ohno, H.; Kato, T. J. Am. Chem. Soc. 2006, 128, 5570-5577.
31. Yamanaka, N.; Kawano, R.; Kubo, W.; Kitamura, T.; Wada, T.; Watanabe, M.; Yanagida, S. Chem. Commun. 2005, 740-742.
32. (a) Hulvat, J. F.; Stupp, S. I. Angew. Chem., Int. Ed. 2003, 42, 778.
33. (b) Hulvat, J. F.; Stupp, S. I. Adv. Mater. 2004, 16, 589-592.
34. (a) Bowlas, C. J.; Bruce, D. W.; Seddon, K. R. Chem. Commun. 1996, 1625.
35. (b) Gordon, C. M.; Holbrey, J. D.; Kennedy, A. R.; Seddon, K. R. J. Mater. Chem. 1998, 8, 2627.
36. (c) Holbrey, J. D.; Seddon, K. R. J. Chem. Soc., Dalton Trans. 1999, 2133.
37. (d) Tosoni, M.; Laschat, S.; Baro, A. Helv. Chim. Acta 2004, 87, 2742.
38. (e) Knight, G. A.; Shaw, B. D. J. Chem. Soc. 1938, 682.
39. (f) Sudholter, E. J. R.; Engberts, J. B. F. N.; de Jeu, W. J. Phys. Chem. 1982, 86, 1908.
40. For example: (a) Hoshino, K.; Yoshio, M.; Mukai, T.; Kishimoto, K.; Ohno, H.; Kato, T. J. Polym. Sci., Part A: Polym. Chem. 2003, 41, 3486.
41. (b) Navarro-Rodriguez, D.; Frere, Y.; Gramain, P.; Guillon, D.; Skoulios, A. Liq. Cryst. 1991, 9, 321.
42. (c) Cui, L.; Sapagovas, V.; Lattermann, G. Liq. Cryst. 2002, 29, 1121.
43. (d) Yoshizawa, H.; Mihara; Koide, N. Mol. Cryst. Liq. Cryst. 2004, 423, 61.
44. (e) El Hamaoui, B.; Zhi, L.; Pisula, W.; Kolb, U.; Wu, J.; Müllen, K. Chem. Commun. 2007, 2384.
45. Motoyanagi, J.; Fukushima, T.; Aida, T. Chem. Commun. 2005, 101.
46. (a) Kosaka, Y.; Kato, T.; Uryu, T. Liq. Cryst. 1995, 18, 693-698.
47. (b) Suisse, J. M.; Bellemin-Laponnaz, S.; Douce, L.; Maisse-Francois, A.; Welter, R. Tetrahedron Lett. 2005, 46, 4303-4305.
48. (a) Altman, R. A.; Buchwald, S. L. Org. Lett. 2006, 8, 2779-2782.
49. (b) Zhang, H.; Cai, Q.; Ma, D. J. Org. Chem. 2005, 70, 5164-5173.
50. (c) Ma, D.; Cai, Q.; Zhang, H. Org. Lett. 2003, 5, 2453.
51. Note that for reactions with the bulky 2-phenylimidazole, we were not able to obtain the high yields reported in literature (ref 18a).
52. Jullien, L.; Canceill, J.; Lacombe, L.; Lehn, J. M. J. Chem. Soc., Perkins Trans. 2 1995, 417-426.
53. Note that more ionic liquid crystals have been synthesized than discussed in the body of the paper. All synthesized materials are in the Supporting Information.
54. Binnemans, K. Chem. Rev. 2005, 105, 4148-4204.