Amide, urea and thiourea-containing triphenylene derivatives: Influence of H-bonding on mesomorphic properties

Liquid Crystals

Volumn 34, Issue 9, 2007, Pages 1029-1038

  Paraschiv, Ioan ^a   Tomkinson, Alistair ^a,b   Giesbers, Marcel ^a   Sudhölter, Ernst J R ^a,c   Zuilhof, Han ^a   Marcelis, Antonius T M ^a  

^a WAGENINGEN UNIVERSITY   (Netherlands)

^b Avantium Technologies BV   (Netherlands)

^c DELFT UNIVERSITY OF TECHNOLOGY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 35048897864     PISSN: 02678292     EISSN: 13665855     Source Type: Journal    
DOI: 10.1080/02678290701609640     Document Type: Article

References (57)

1. (a) N. Boden, R.J. Bushby, A.N. Cammidge, G.J. Headdock. J. Mater. Chem., 5, 2275 (1995);
2. (b) S. Kumar. Liq. Cryst., 32, 1089 (2005);
3. (c) S. Kumar. Chem. Soc. Rev., 35, 83 (2006).
4. A.C. Grimsdale, K. Müllen. Angew. Chem. Int. Ed., 44, 5592 (2005).
5. (a) D. Adam, P. Schuhmacher, J. Simmerer, L. Häussling, K. Siemensmeyer, K.H. Etzbach, H. Ringsdorf, D. Haarer. Nature, 371, 141 (1994);
6. (b) C.W. Struijk, A.B. Sieval, J.E.J. Dakhorst, M. van Dijk, P. Kimkes, R.B.M. Koehorst, H. Donker, T.J. Schaafsma, S.J. Picken, A.M. van de Craats, J.M. Warman, H. Zuilhof, E.J.R. Sudhölter. J. Am. chem. Soc., 122, 11057 (2000).
7. J.L. Brédas, J.P. Calbert, D.A. da Silva Filho, J. Cornil. Proc. natl. Acad. Sci. U.S.A., 99, 5804 (2002).
8. (a) G. Lüssem, J.H. Wendorff. Polym. Adv. Technol., 9, 443 (1998);
9. (b) I. Seguy, P. Destruel, H. Boch. Synth. Meth., 111-112, 15 (2000);
10. (c) I. Seguy, P. Jolinat, J. Farenc, R. Mamy, H. Bock, J. Ip, T.P. Nguyen. J. appl. Phys., 89, 5442 (2001);
11. (d) L. Schmidt-Mende, A. Fechtenkötter, K. Müllen, E. Moons, R.H. Friend, J.D. MacKenzie. Science, 293, 1119 (2001);
12. (e) L. Schmidt-Mende, A. Fechtenkötter, K. Müllen, R.H. Friend, J.D. MacKenzie. Physica E, 14, 263 (2002);
13. (f) N. Stutzmann, R.H. Friend, H. Sirringhaus. Science, 299, 1881 (2003).
14. K. Itaka, M. Yamashiro, J. Yamaguchi, M. Haemori, S. Yaginuma, Y. Matsumoto, M. Kondo, H. Koinuma. Adv. Mater., 18, 1713 (2006).
15. N. Boden, R.J. Bushby, J. Clements, B.J. Movaghar. J. Mater. Chem., 9, 2081 (1999).
16. (a) F.M. Mulder, J. Stride, S.J. Picken, P.H.J. Kouwer, M.P. de Haas, L.D.A. Siebbeles, G.J. Kearly. J. Am. chem. Soc., 125, 3860 (2003);
17. (b) G.J. Kearly, F.M. Mulder, S.J. Picken, P.H.J. Kouwer, J. Stride. J. chem. Phys., 292, 185 (2003);
18. (c) G. Cinacchi, R. Colle, A. Tani. J. phys. Chem. B, 108, 7969 (2004);
19. (d) M. Lehmann, G. Kestemont, R.G. Aspe, C. Buess-Herman, M.H.J. Koch, M.G. Debije, J. Piris, M.P. de Haas, J.M. Warman, M.D. Watson, V. Lemaur, J. Cornil, Y.H. Geerts, R. Gearba, D.A. Ivanov. Chem. Eur. J., 11, 3349 (2005).
20. (a) V. Percec, C.M. Mitchell, W.D. Cho, S. Uchida, M. Glodde, G. Ungar, X. Zeng, Y. Liu, V.S.K. Balagurusamy, P.A. Heiney. J. Am. chem. Soc., 126, 6078 (2004);
21. (b) T. Kajitani, S. Kohmoto, M. Yamamoto, K. Kishikawa. J. Mater. Chem., 14, 3449 (2004).
22. (a) M. Suárez, J.M. Lehn, S.C. Zimmerman, A. Skoulios, B. Heinrich. J. Am. chem. Soc., 120, 9526 (1998);
23. (b) T. Kato. Struct. Bonding, 96, 95 (2000);
24. (c) L.J. Prins, D.N. Reinhoudt, P. Timmerman. Angew. Chem. Int. Ed., 40, 2382 (2001);
25. (d) U. Beginn. Prog. Polym. Sci., 28, 1049 (2003);
26. (e) T. Kato, N. Mizoshita, K. Kishimoto. Angew. Chem. Int. Ed., 45, 38 (2006).
27. I. Paraschiv, P. Delforterie, M. Giesbers, M.A. Posthumus, A.T.M. Marcelis, H. Zuilhof, E.J.R. Sudhölter. Liq. Cryst., 32, 977 (2005).
28. R.I. Gearba, M. Lehmann, J. Levin, D.A. Ivanov, M.H.J. Koch, J. Barberá, M.G. Debije, J. Piris, Y.H. Geerts. Adv. Mater., 15, 1614 (2003).
29. C.Y. Liu, A.J. Bard. Nature, 418, 162 (2005).
30. J.C. Beeson, L.J. Fitzgerald, J.C. Gallucci, R.E. Gerkin, J.T. Rademacher, A.W. Czarnik. J. Am. chem. Soc., 116, 4621 (1994).
31. I. Paraschiv, M. Giesbers, B. van Lagen, F.C. Grozema, R.D. Abellon, L.D.A. Siebbeles, A.T.M. Marcelis, H. Zuilhof, E.J.R. Sudhölter. Chem. Mater., 18, 968 (2006).
32. (a) J. Cornil, V. Lemaur, J.P. Calbert, J.L. Brédas. Adv. Mater., 14, 726 (2002);
33. (b) J. Tant, Y.H. Geerts, M. Lehmann, V. De Cupere, G. Zucchi, B.W. Laursen, T. Bjørnholm, V. Lemaur, V. Marcq, A. Burquel, E. Hennebicq, F. Gardebien, P. Viville, D. Beljonne, R. Lazzaroni, J. Cornil. J. phys. Chem. B, 109, 20315 (2005).
34. Y. Matsunaga, N. Miyajima, Y. Nakayasu, S. Sakai, M. Yonenaga. Bull. chem. Soc. Japan, 61, 207 (1988).
35. (a) M.L. Bushey, A. Hwang, P.W. Stephens, C. Nuckolls. Angew. Chem. Int. Ed., 41, 2828 (2002);
36. (b) L. Brunsveld, B.J.B. Folmer, E.W. Meijer, R.P. Sijbesma. Chem. Rev., 101, 4071 (2001);
37. (c) T.Q. Nguyen, M.L. Bushey, L.E. Brus, C. Nuckolls. J. Am. chem. Soc., 124, 15051 (2002);
38. (d) J.J. van Gorp, J.A.J.M. Vekemans, E.W. Meijer. J. Am. chem. Soc., 124, 14759 (2002).
39. K.Q. Zhao, C.Y. Gao, P. Hu, B.Q. Wang, Q. Li. Acta chim. Sinica, 64, 1051 (2006).
40. (a) S.P. Brown, I. Schnell, J.D. Brand, K. Müllen, H.W. Spiess. Phys. Chem. chem. Phys., 2, 1735 (2000);
41. (b) W. Wan, H. Monobe, T. Sugino, Y. Tanaka, Y. Shimizu. Mol. Cryst. liq. Cryst., 364, 597 (2001);
42. (c) Y. Setoguchi, H. Monobe, W. Wan, N. Terasawa, K. Kiyohara, N. Nakamura, Y. Shimizu. Thin Solid Films, 438-439, 407 (2003).
43. Z. Yildirim, E. Mendes, S.J. Picken, I. Paraschiv, A.T.M. Marcelis, H. Zuilhof, W.M. de Vos, E.J.R. Sudhölter. Mol. Cryst. liq. Cryst., 439, 237/2103 (2005).
44. W. Wan, H. Monobe, Y. Tanaka, Y. Shimizu. Liq. Cryst., 31, 571 (2003).
45. (a) J.H. van Esch, S. De Feyter, R.M. Kellogg, F. De Schryver, B.L. Feringa. Chem. Eur. J., 3, 1238 (1997);
46. (b) J. H. van Esch, F. Schoonbeek, M. de Loos, H. Kooijman, A.L. Spek, R.M. Kellogg, B.L. Feringa. Chem. Eur. J., 5, 937 (1999);
47. (c) F.S. Schoonbeek, J.H. van Esch, B. Wegewijs, D.B.A. Rep, M.P. de Haas, T.M. Klapwijk, R.M. Kellogg, B.L. Feringa. Angew. Chem. Int. Ed., 38, 1393 (1999);
48. (d) F.S. Schoonbeek, J.H. van Esch, R. Hulst, R.M. Kellogg, B.L. Feringa. Chem. Eur. J., 6, 2633 (2000).
49. A. Masunov, J.J. Dannenberg. J. phys. Chem. B, 104, 806 (2000).
50. (a) S.P. Brown, I. Schnell, J.D. Brand, K. Müllen, H.W. Spiess. J. Mol. Struct., 521, 179 (2000);
51. (b) M.D. Watson, F. Jäckel, N. Severin, J.P. Rabe, K. Müllen. J. Am. chem. Soc., 126, 1402 (2004).
52. (a) W. Fimmen, B. Glüsen, A. Kettner, M. Wittenberg, J.H. Wendorff. Liq. Cryst., 23, 569 (1997);
53. (b) N. Terasawa, H. Monobe, K. Kiyohara, Y. Shimizu. Chem. Lett., 32, 214 (2003);
54. (c) J. Motoyanagi, T. Fukushima, T. Aida. Chem. Commun., 101 (2005).
55. (a) M. Kardan, B.B. Reinhold, S.L. Hsu, R. Thakur, C.P. Lillya. Macromolecules, 19, 616 (1986);
56. (b) T.S. Perova, J.K. Vij, A. Kocot. Adv. chem. Phys., 113, 341 (2000).
57. A. Kettner, J.H. Wendorff. Liq. Cryst., 26, 483 (1999).