The X-Ray Crystal Structures and Computational Analysis of NH…π Hydrogen Bonded Banana-Shaped Carbazole Derivatives and Thermal Analysis of Higher Mesogenic Homologues

References

• Link , J. T. , Raghavan , S. , Gallant , M. , Danishefsky , S. , Chou , T. C. and Ballas , L. M. 1996 . J. Am. Chem. Soc. , 118 : 2825 (b) Y. Yamashita, N. Fujii, C. Murkata, T. Ashiawa, M. Okabe, H. Nakano, Biochemistry, 31, 12069 (1992). (c) D. P. Chakraborty, Prog. Chem. Org. Nat. Prod. Vol. 34.
   Web of Science ®Google Scholar
• Zhang , Y. , Wada , T. and Sasabe , H. 1998 . J. Mater. Chem. , 8 : 809
   Web of Science ®Google Scholar
• Ashkin , A. , Boyd , G. D. , Dziedic , J. M. , Smith , R. G. , Ballman , A. A. and Nassau , K. 1966 . Appl. Phys. Lett. , 9 : 72 The space charge field induced photorefractive effect was first observed in inorganic electro-optic LiNbO3 crystals by
   Web of Science ®Google Scholar
• Zhang , Y. , Cui , Y. and Prasad , P. N. 1992 . Phys. Rev. B , 46 : 9900 The first report of a carbazole containing photorefractive material was by
   Web of Science ®Google Scholar
• Günter , P. and Huignardm , J.-P. , eds. 1988 . Photorefractive Materials and Their Applications , New York : Springer-Verlag . For example of holographic application see; M. D. Rahn, D. P. West, J. D. Shakos, J. Appl. Phys., 87, 627 (2000)
   Google Scholar
• Maruyama , S. , Tao , X.-t. , Hokari , H. , Noh , T. , Zhang , Y. , Wada , T. , Sasabe , H. , Watanabe , T. and Miyata , S. 1999 . J. Mater. Chem. , 9 : 893 For a related a related topic on fluorescent LEDs see; M. A. Baldo, M. E. Thompson, S. R. Forest, Nature, 403, 750 (2000).
   Web of Science ®Google Scholar
• Zhang , Y. , Wang , L. , Wada , T. and Sasabe , H. 1996 . Chem. Commun. , 559
   Google Scholar
• Scott , J. C. , Pautmeier , L. Th. and Moerner , W. E. 1992 . J. Opt. Soc. Am. B , 9 : 2059
   Web of Science ®Google Scholar
• Ducharme , S. , Scott , J. C. , Twieg , R. J. and Moerner , W. E. 1991 . Phys. Rev. Lett. , 66 : 1846 The first report of an amorphous organic photorefractive material was by
   PubMed Web of Science ®Google Scholar
• Sutter , K. , Hulliger , J. and Günter , P. 1990 . Solid State Chem. , 74 : 867
   Web of Science ®Google Scholar
• Zhang , Y. , Wada , T. , Wang , L. and Sasabe , H. 1997 . Chem. Mater. , 9 : 2798
   Web of Science ®Google Scholar
• Lux , M. and Strohriegl , P. 1987 . Makromol. Chem. , 188 : 811 The carbazole moiety has been introduced into a low molecular weight calamitic mesogenic structures which diplays a nematic mesophase, see
   Web of Science ®Google Scholar
• Marcher , B. , Chapoy , L. and Christensen , D. H. 1988 . Macromolecules , 21 : 677
   Web of Science ®Google Scholar
• Demus , D. , Goodby , J. , Gray , G. W. , Speiss , H.-W. and Vill , V. , eds. 1998 . Handbook of Liquid Crystals , Vol. 2B , 693 – 780 . Weinheim : Wiley-VCH .
   Google Scholar
• Meyer , R. B. 1977 . Mol. Cryst. Liq. Cryst. , 40 : 33
   Web of Science ®Google Scholar
• Niori , T. , Sekine , T. , Watanabe , J. , Furukawa , T. and Takezoe , H. 1996 . J. Mater. Chem. , 6 : 1231 – 1233 . For the first report regarding bent shaped mesogens and their modification to smectic phases see; 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) and D. Vorlander, A. Apel, Ber. Dtsch. Chem. Ges., 65, 1101 (1932). 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: (a) D. Shen, S. Diele, G. Pelz, I. Wirth, C. Tschierske, J. Mater. Chem., 9, 661 (1999), (b) A. S. Matharu, C. Grover, L. Kmoitov, G. Andersson, J. Mater. Chem., 10, 1303, (2000) 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).
   Web of Science ®Google Scholar
• Meyer , R. B. , Liebert , L. , Strzelecki , L. and Keller , P. 1975 . J. Phys. Lett. , 36 : L-69 Ferroelectric liquid crystals were first postulated and observed in chiral mesogenic structures that induced polar ordering, see; (b) N. A. Clarke, S. T. Lagerwall, Appl. Phys. Lett., 38, 899 (1980). Later banana-shaped mesogens 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) 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.
   Google Scholar
• Manickam , M. , Kumar , S. , Preece , J. A. and Spencer , N. 2000 . Liq. Cryst. , 27 : 703
   Web of Science ®Google Scholar
• Sekine , T. , Niori , T. , Sone , M. , Watanabe , J. , Choi , S. W. , Takanishi , Y. and Takezoe , H. 1997 . Jpn J. Appl. Phys. , 36 : 6455
   Web of Science ®Google Scholar
• Pelzl , G. , Diele , S. , Jakli , A. , Lischka , C. , Wirth , I. and Weissflog , W. 1999 . Liq. Cryst. , 26 : 135
   Web of Science ®Google Scholar
• Shen , D. , Diele , S. , Pelzl , G. , Wirth , I. and Tschierske , C. 1999 . J. Mater. Chem. , 6 : 661
   Google Scholar
• Shen , D. , Diele , S. , Wirth , I. and Tschierske , C. 1998 . Chem. Commun. , : 2573
   Web of Science ®Google Scholar
• Pelzl , G. , Diele , S. , Grande , S. , Jakli , A. , Lischka , C. , Kresse , H. , Schmalfuss , H. , Wirth , I. and Weissflog , W. 1999 . Liq. Cryst. , 26 : 401
   Web of Science ®Google Scholar
• Levitsky , I. A. , Kishikawa , K. , Eichhorn , S. H. and Swager , T. M. 2000 . J. Am. Chem. Soc. , 122 : 2474
   Web of Science ®Google Scholar
• Weissflog , W. , Lischka , C. , Benne , I. , Scharf , T. , Pelzl , G. , Diele , S. and Kruth , H. 1998 . Proc. SPIE: Int. Soc. Opt. Eng. , 3319 : 14
   Google Scholar
• Biali , S. E. and Rappoport , Z. 1984 . J. Am. Chem. Soc. , 106 : 5641 For literature on X-H…π hydrogen bonds, see: a); b) M. G. B. Drew, G. R. Willey, J. Chem. Soc. Perk. Trans. 2, 215–220 (1986); c) H. S. Rzepa, M. L. Webb, A. M. Z. Slawin, D. J. Williams, J. Chem. Soc., Chem. Commun., 765–768 (1991), D. A. Rodham. S. Suzuki, R. D. Suenram. F. J. Lovas, D. Dasgupta, G. A. Blake, Nature, 362 (1993). 735–737; d) H. Adams, K. D. M. Harris, G. A. Hembury, C. A. Hunter, D. Livingston, J. M. McCabe, Chem. Commun., 2351–2352 (1996); e) A. P. Bisson, V. M. Lynch, M. K. C. Monahan, E. V. Anslyn, Angew. Chem. Int. Ed. Engl., 36, 2340–2342 (1997).
   Google Scholar
• Bel'skii , V. K. 1985 . Kristallografiya , 30 : 193
   Google Scholar
• Pelz , G. , Diele , S. and Weissflog , W. 1999 . Adv. Mater. , 11 : 707 For an excellent review on banana-shaped liquid crystalline materials see;
   Web of Science ®Google Scholar
• 1993 . Molecular Structure Corporation , TX, USA : The Woodlands . TEXSAN. Single Crystal Structure Analysis Software. Version 1. 6. MSC, 3200 Research Forest Drive., 77381
   Google Scholar
• Sheldrick , G. M. 1993 . SHELXL92. Program for the Refinement of Crystal Structures , Germany : University of Gottingen .
   Google Scholar
• Stewart , J. J. P. Mopac VI. , QCPE #455.
   Google Scholar
• Dewar , M. J. S. , Zoebisch , E. G. , Healy , E. F. and Stewart , J. J. P. 1985 . J. Am. Chem. Soc. , 107 : 3902 – 3909 .
   Web of Science ®Google Scholar
• Besler , B. H. , Merz , K. M. Jr. and Kollman , P. A. 1990 . J. Comp. Chem. , 11 : 431 – 439 .
   Web of Science ®Google Scholar
• Nichols , A. , Sharp , K. and Honig , B. 1991 . Proteins: Structure, Function and Genetics , 11 : 281
   Google Scholar
• Smith , K. , James , D. M. , Mistry , A. G. , Bye , M. R. and Faulkner , D. J. 1992 . Tetrahedron , 48 : 7479 – 7488 .
   Web of Science ®Google Scholar
• Dauben , W. G. and Tilles , H. 1950 . J. Am. Chem. Soc. , 72 : 3185 – 3187 .
   Google Scholar
• Konig , W. and Scharrnbeck , W. 1930 . J. Prakt. Chem. , : 153 – 170 .
   Google Scholar