Smectic bimetallomesogens in β-enaminoketonate copper complexes: the steric effect of a methyl substituent on the core group and the crystal structure

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Chung K. Lai, Raymond Lin, Min-Yi Lu and Kwo-Cheng Kao


Abstract

A systematic study has been made of the liquid crystalline properties of two types of copper complexes derived from enamino-β-ketonate and iminopropyl-β-ketonate Schiff bases that exhibit mesomorphism. These complexes are structurally similar, and all have a bimetallic center as an expanded core group. The mesophase stability depends upon the steric bulk between the layer structures. The enamino-β-ketonate complexes exhibit smectic A phases, however, the iminopropyl-β-diketonates are not liquid crystalline. Examination of the structural features of these complexes revealed that the presence of a methyl group attached to the core group was the cause for the lack of liquid crystallinity observed in the latter. The crystal and molecular structure of bis[3,5-dioctanoylphenyl 2-(3-hydroxypropyl)iminopropyl ketonato]copper(II) was determined by means of X-ray analysis. The Cu[hair space][hair space]· · ·[hair space][hair space]Cu intramolecular separation is 3.0375(5) Å. The planar geometry is slightly distorted toward square pyramidal by displacement of the copper by 0.018 Å from the mean plane through atoms N(1), O(2), O(1A) and O(1).


References

  1. (a) S. A. Hudson and P. M. Maitlis, Chem. Rev., 1993, 93, 861 CrossRef CAS; (b) P. Espinet, M. A. Esteruelas, L. A. Oro, J. L. Serrano and E. Sola, Coord. Chem. Rev., 1992, 117, 215 CrossRef CAS; (c) J. L. Serrano, in Metallomesogens, Synthesis, Properties, and Applications, VCH, New York, 1996 Search PubMed.
  2. P. Maitlis and A. M. Giroud-Godquin, Angew. Chem., Int. Ed. Engl., 1991, 30, 375 CrossRef.
  3. M. Marcos, P. Romero and J. L. Serrano, Liq. Cryst., 1990, 7, 251 CAS; Mol. Cryst. Liq. Cryst., 1989, 167, 123 Search PubMed; E. Campillos, M. Marcos and J. L. Serrano, J. Mater. Chem., 1993, 3, 1049 Search PubMed.
  4. B. Mühlberger and W. Haase, Liq. Cryst., 1989, 5, 251; C. Cativiela, J. L. Serrano and M. M. Zurbano, J. Org. Chem., 1995, 60, 3074 CrossRef CAS; X. Yang, Q. Lu, S. Dong, D. Liu, S. Zhu, F. Wu and R. Zhang, J. Phys. Chem., 1993, 97, 6726 CrossRef CAS; S. N. Poelsma, A. H. Servante, F. P. Fanizzi and P. M. Maitlis, Liq. Cryst., 1994, 16, 675 CAS; H. Zheng, P. J. Carroll and T. M. Swager, Liq. Cryst., 1993, 14, 1421 CrossRef CAS; K. Ohta, M. Yokoyama and H. Mikawa, Mol. Cryst. Liq. Cryst., 1981, 73, 205 CAS.
  5. C. K. Lai and Y.-F. Leu, J. Chin. Chem. Soc., 1997, 44, 89 CAS.
  6. C. K. Lai, M.-Y. Lu and F.-J. Lin, Liq. Cryst., 1997, 23, 313 CrossRef.
  7. W. Pyzuk, E. Górecka and A. Krowczynski, Liq. Cryst., 1992, 11, 797 CAS; W. Pyzuk, E. Górecka, A. Krowczynski and J. Przedmojski, Liq. Cryst., 1993, 14, 773 CAS; E. Górecka, W. Pyzuk, A. Krowczynski and J. Przedmojski, Liq. Cryst., 1993, 14, 1837 CAS.
  8. J. F. Frejmanis, Chemistry of Enaminoketones, enaminoimines, enaminothiones(in Russian), Izd. Zinatie, 1974 Search PubMed; W. Pyzuk, A. Krowczynski and E. Górecka, Liq. Cryst., 1991, 10, 593 Search PubMed.
  9. G. R. Newkome and T. Kawato, Inorg. Chim. Acta, 1979, 37, L481 CrossRef CAS; D. E. Fenton, C. M. Regan, U. Casellato, P. A. Vigato and M. Vidali, Inorg. Chim. Acta, 1982, 58, 83 CrossRef CAS; S. Yamada, Y. Kuge and K. Yamanouchi, Inorg. Chim. Acta, 1967, 1, 139 CrossRef CAS; J. A. Bertrand and R. I. Kaplan, Inorg. Chem., 1965, 4, 1657 CrossRef CAS; J. A. Davis and E. Sinn, J. Chem. Soc., Dalton Trans., 1976, 165 RSC.
  10. C. K. Johnson, ORTEP, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, TN, 1976.
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