The X-ray crystal structures and computational analysis of NH...π hydrogen bonded banana-shaped carbazole derivatives and thermal analysis of higher mesogenic homologues

Molecular Crystals and Liquid Crystals Science and Technology Section A: Molecular Crystals and Liquid Crystals

Volumn 369, Issue , 2001, Pages 17-35

  Belloni, Maura ^a   Manickam, M ^a   Ashton, Peter R ^a   Kariuki, Benson M ^a   Preece, Jon A ^a   Spencer, Neil ^a   Wilkie, John ^a  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

Author keywords

Banana; Carbazole; Liquid crystals; N H hydrogen bonding

Indexed keywords

EID: 2942656639     PISSN: 1058725X     EISSN: None     Source Type: Journal    
DOI: 10.1080/10587250108030006     Document Type: Article

References (55)

1. (a) J.T. Link, S. Raghavan. M. Gallant, S. Danishefsky, T.C. Chou, L.M. Ballas, J. Am. Chem. Soc. 118, 2825 (1996).
2. (b) Y. Yamashita, N. Fujii. C. Murkata, T. Ashiawa, M. Okabe, H. Nakano, Biochemistry 31, 12069 (1992).
3. (c) D.P. Chakraborty, Prog. Chem. Org. Nat. Prod. Vol. 34.
4. Y. Zhang, T. Wada, H. Sasabe, J. Mater. Chem. 8, 809 (1998).
5. 3 crystals by A. Ashkin, G.D. Boyd, J.M. Dziedic, R.G. Smith, A. A Ballman, K. Nassau, Appl. Phys. Lett. 9, 72 (1966).
6. The first report of a carbazole containing photorefractive material was by Y. Zhang, Y. Cui, P.N. Prasad, Phys. Rev. B 46, 9900 (1992).
7. P. Günter, J.-P. Huignardm, Eds Photorefractive Materials and Their Applications; Springer-Verlag, New York, 1988. For example of holographic application
8. see; M.D. Rahn, D.P. West, J.D. Shakos, J. Appl. Phys. 87, 627 (2000).
9. S. Maruyama, X.-t. Tao. H. Hokari, T. Noh, Y. Zhang, T. Wada. H. Sasabe, T. Watanabe. S. Miyata, J. Mater. Chem. 9, 893 (1999).
10. For a related a related topic on fluorescent LEDs see; M.A. Baldo, M.E. Thompson, S.R. Forest, Nature 403, 750 (2000).
11. Y. Zhang, L. Wang, T. Wada, H. Sasabe, Chem. Commun. 559 (1996).
12. J.C. Scott, L. Th. Pautmeier, W.E. Moerner, J. Opt. Soc. Am. B 9, 2059 (1992).
13. The first report of an amorphous organic photorefractive material was by S. Ducharme, J.C. Scott, R.J. Twieg, W.E. Moerner, Phys. Rev. Lett. 66, 1846 (1991).
14. K. Sutter, J. Hulliger. P. Günter, Solid State Chem. 74, 867 (1990).
15. Y. Zhang, T. Wada, L. Wang, H. Sasabe, Chem. Mater. 9, 2798 (1997).
16. The carbazole moiety has been introduced into a low molecular weight calamitic mesogenic structures which diplays a nematic mesophase, see M. Lux, P. Strohriegl, Makromol. Chem. 188, 811 (1987).
17. B. Marcher, L. Chapoy, D.H. Christensen, Macromolecules 21, 677 (1988).
18. D. Demus, J. Goodby, G.W. Gray, H.-W. Speiss, V. Vill, (eds), 1998, Handbook of Liquid Crystals vol. 2B(Weinheim: Wiley-VCH) pp 693-780.
19. R.B. Meyer, Mol. Cryst. Liq. Cryst. 40, 33 (1977).
20. For the first report regarding bent shaped mesogens and their modification to smectic phases see; T. Niori, T. Sekine, J. Watanabe, T. Furukawa, H. Takezoe, J. Mater. Chem. 6, 1231-1233 (1996).
21. However, it is interesting to note that Vorlander and Apel synthesised bent shaped mesogens back in 1929, see; D. Vorlander, Ber. Dtsch. Chem. Ges. 63, 2831 (1929)
22. and D. Vorlander, A. Apel, Ber. Dtsch. Chem. Ges. 65, 1101 (1932).
23. Additionally, Akutagawa published four bent compounds in 1994 which exhibited smectic mesophases but no structural peculiarties were noted, see; T. Akutagawa, Y. Matsunaga, K. Yasuhara, Liq. Cryst. 17, 659 (1994). The term banana for the description of the molecular shape has evolved from the fact that the first bent mesogens had flexible linkers around a bent 1,3-substituted benzene moiety and were qualified as being statistically bent, see for example;
24. (a) D. Shen, S. Diele, G. Pelz, I. Wirth, C. Tschierske, J. Mater. Chem. 9, 661 (1999),
25. (b) A.S. Matharu, C. Grover, L. Kmoitov, G. Andersson, J. Mater. Chem. 10, 1303, (2000)
26. whilst some later structures had much more rigid bent molecular motifs and were referred to as boomerang shaped mesogens, see for example; T.J. Dingemans, E.T. Samulski, Liq. Cryst. 27, 131 (2000).
27. Ferroelectric liquid crystals were first postulated and observed in chiral mesogenic structures that induced polar ordering, see (a) R.B. Meyer, L. Liebert, L. Strzelecki, P. Keller, J. Phys. Lett. 36, L-69, (1975);
28. (b) N.A. Clarke, S.T. Lagerwall, Appl. Phys. Lett. 38, 899 (1980).
29. Later banana-shaped mes-ogens were also shown to exhibit ferroelectric behaviour, see (a) T. Niori, T. Sekine, J. Watanabe, T. Furukawa, H. Takezoe, J. Mater. Chem. 6, 1231 (1996)
30. for the first report and (b) D.M. Walba, E. Körblova. R. Shao, J.E. Maclennan, D.R. Link, M.A. Glaser, N.A. Clark, Science 288, 2181-2184 (2000) for a recent report.
31. M. Manickam, S. Kumar, J.A. Preece, N. Spencer, Liq. Cryst. 27, 703 (2000).
32. T. Sekine, T. Niori, M. Sone, J. Watanabe, S.W. Choi, Y. Takanishi, H. Takezoe, Jpn J. Appl. Phys. 36, 6455 (1997).
33. G. Pelzl, S. Diele, A. Jakli, C. Lischka, I. Wirth, W. Weissflog, Liq. Cryst. 26, 135 (1999).
34. D. Shen, S. Diele,G. Pelzl, I. Wirth, C. Tschierske, J. Mater. Chem. 6, 661 (1999).
35. D. Shen, S. Diele, I. Wirth, C. Tschierske, Chem. Commun. 2573 (1998).
36. G. Pelzl, S. Diele, S. Grande, A. Jakli, C. Lischka. H. Kresse. H. Schmalfuss, I. Wirth, W. Weissflog. Liq. Cryst. 26, 401 (1999).
37. I.A. Levitsky, K. Kishikawa, S.H. Eichhorn, T.M. Swager, J. Am. Chem. Soc. 122, 2474 (2000).
38. W. Weissflog, C. Lischka, I. Benne, T. Scharf, G. Pelzl, S. Diele, H. Kruth, Proc. SPIE: Int. Soc, Opt. Eng. 3319, 14 (1998).
39. For literature on X-H⋯π hydrogen bonds, see: a) S.E. Biali, Z. Rappoport, J. Am. Chem. Soc. 106, 5641(1984);
40. b) M.G.B. Drew, G.R. Willey. J. Chem. Soc. Perk Trans. 2, 215-220 (1986);
41. H.S. Rzepa, M.L. Webb, A.M.Z. Slawin, D.J. Williams, J. Chem. Soc., Chem. Commun., 765-768(1991);
42. D.A. Rodham. S. Suzuki, R.D. Suenram, F.J. Lovas, D. Dasgupta, G.A. Blake, Nature 362 (1993), 735-737;
43. H. Adams, K.D.M. Harris. G.A. Hembury, C.A. Hunter, D. Livingston, J.M. McCabe, Chem. Commun., 2351-2352 (1996);
44. e) A.P. Bisson, V.M. Lynch, M.K.C. Monahan, E.V. Anslyn, Angew. Chem. Int. Ed. Engl. 36, 2340-2342 (1997).
45. V.K. Bel'skii, Kristallografiya 30, 193 (1985).
46. For an excellent review on banana-shaped liquid crystalline materials see: G. Pelz, S. Diele, W. Weissflog, Adv. Mater. 11, 707 (1999).
47. Molecular Structure Corporation (1993). TEXSAN. Single Crystal Structure Analysis Software. Version 1.6. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA.
48. Sheldrick. G.M. (1993). SHELXL92. Program for the Refinement of Crystal Structures. University of Gottingen, Germany.
49. J.J.P. Stewart. Mopac VI. QCPE #455.
50. M.J.S. Dewar. E.G. Zoebisch, E.F. Healy, J.J.P. Stewart. J. Am. Chem. Soc. 107, 3902-3909 (1985).
51. B.H. Besler, K.M. Merz, Jr., P.A. Kollman. J. Comp. Chem. 11, 431-439 (1990).
52. A. Nichols, K. Sharp, B. Honig. Proteins: Structure, Function and Genetics 11, 281 (1991).
53. K. Smith, D.M. James, A.G. Mistry, M.R. Bye and D.J. Faulkner. Tetrahedron 48, 7479-7488 (1992).
54. W.G. Dauben, H. Tilles, J. Am. Chem. Soc. 72, 3185-3187 (1950).
55. W. Konig, W. Scharmbeck, J. Prakt. Chem. 153-170 (1930).