Hostname: page-component-586b7cd67f-2brh9 Total loading time: 0 Render date: 2024-11-25T17:34:14.180Z Has data issue: false hasContentIssue false
  • English
  • Français

Design and synthesis of ferroelectric liquid crystals. 24. Incorporation of the disperse red 1 chromophqre into side-by-side dimers for nonlinear optics

Published online by Cambridge University Press:  10 February 2011

Daniel J. Dyer ,
Renfan Shao ,
Noel A. Clark  and
David M. Walba
Daniel J. Dyer
Affiliation:
Department of Chemistry and Biochemistry
Renfan Shao
Affiliation:
Department of Physics, and Optoelectronic Computer System Center, University of Colorado, Boulder CO 80309-0215
Noel A. Clark
Affiliation:
Department of Physics, and Optoelectronic Computer System Center, University of Colorado, Boulder CO 80309-0215
David M. Walba
Affiliation:
Department of Chemistry and Biochemistry
Get access

Abstract

With excellent processibility on silicon integrated circuits and thermodynamically stable polar order, ferroelectric liquid crystals (FLCs) show great potential as components of fast integrated electro-optic modulators. In order to realize this potential, however, an increase in the magnitude of the electronic secona order nonlinear susceptibility χ(2) is required. This has been problematical since functional arrays with large molecular second order susceptibility β orient with improper supermolecular stereocontrol (i.e. with the charge transfer axis normal to the polar axis) when incorporated into traditional FLC structures. Herein we present examples of a new LC structural class designed to achieve the proper supermolecular structure for large χ(2) in FLCs. The observed sign and magnitude of the ferroelectric polarization of the new mesogens extrapolated from smectic C* mixtures is fully consistent with the desired supermolecular structure.

Type
Research Article
Information
MRS Online Proceedings Library (OPL) , Volume 413: Symposium W – Electrical, Optical, and Magnetic Properties of Organic Solid State Materials III , 1995 , 357
Copyright
Copyright © Materials Research Society 1996

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

REFERENCES

1 For previous papers in the series see: (a) Walba, D. M.; Dyer, D. J.; Cobben, P. L.; Sierra, T.; Rego, J. A.; Liberko, C. A.; Shao, R.; Clark, N. A. Ferroelectric Liquid Crystals for Nonlinear Optics Applications: Can we Really Do It?; in Thin Films for Integrated Optics Applications, Wessels, B. W., Marder, S. R. and Walba, D. M., Eds.; Materials Research Society: Pittsburgh, PA, 1995; Vol.392, pp 157–162, and references therein. (b) Walba, D.M.; Dyer, D.J.; Sierra, T.; Cobben. P.L.; Shao, R.; Clark, N.A. J. Am. Chem. Soc. 1996, In Press.Google Scholar
2 Arnett, K. E.; Walba, D. M.; Drewes, J. A. Technique for Measuring Electonic-Based Electro-Optic Coefficients for Ferroelectric Liquid Crystals; in Thin Films for Integrated Optics Applications, Wessels, B. W., Marder, S. R. and Walba, D. M., Eds.; Materials Research Society: Pittsburgh, PA, 1995; Vol.392, pp 135–146.Google Scholar
3 (a) Walba, D.M.; Ros, M.B.; Sierra, T.; Rego, J.A.; Clark, N.A.; Shao, R.; Wand, D.M.; Vohra, R.T.; Arnett, K.E.; Velsco, S.P. Ferroelectrics 1991, 121, 247. (b) Schmitt, K.; Herr, R.P.; Schadt, M. FUnschilling, J.; Buchecker, R.; Chen, X.H.; Benecke, C. Liq. Crrst. 1993, 14, 1735.Google Scholar
4 Walba, D.M. Science 1995, 270, 250.Google Scholar
5 (a) Williams, D.J. Angew. Chem., Int. Ed. Engd. 1984, 23,690. (b) Quantum Chemical Computational Calculation of Nonlinear Susceptibilities of Organic Materials; Bredas, J.L.; Garito, A.F.; Ito, Y., Eds.; Special Issue of Mol. Cryst. Liq. Cryst. Sci. Technol., Sect. B; Gordon & Breach: Basel, Switzerland, 1994; Vol.6 (3–4), pp 135. (c) Kanis, D.R.; Ratner, M.A.; Marks, T.J. Chem. Rev. 1994, 94, 195. (d) Meyers, F.; Marder, S.R.; Pierce, B.M.; Bredas, J.L. J. Am. Chem. Soc. 1994, 116, 10703.Google Scholar
6 Kobayashi, S.; Ishibashi, S.; Tsuru, S. Mol. Cryst. Liq. Cryst. Letters 1990, 7, 105.Google Scholar
7 Interesting examples include: (a) Fouquey, C.; Lehn, J.M.; Malthete, J. J. Chem. Soc. Chem. Commun. 1987, 1424. (b) Berdague, P.; Bayle, J.P.; Ho, M.S.; Fung, B.M. Liq. Crvst. 1993, 14, 667. (c) Ikeda, T.; Sasaki, T.; Ichimura, K. Nature 1993, 361, 428. (d) Sasaki, T.; Ikeda, T.; Ichimura, K. J. Am. Chem. Soc. 1994, 116., 625.Google Scholar
8 Some examples of LC dopants with negative dichroism, wherein dye units orient at a large angle relative to the LC director upon dissolution in an LC host, have been reported: (a) Ivashchenko, A.V.; Petrova, O.S.; Titiov, V.V. Mol. Cryst. Liq. Cryst. 1984, 108, 51. (b) Rumyantsev, V.G.; Ivashchenko, A.V.; Muratov, V.M.; Lazarreva, V.T.; Prudnikova, E.K.; Blinov, L.M. Mol. Cryst. Liq. Cryst. 1983, 94, 205. See also reference 1.Google Scholar
9 Walba, D.M. Ferroelectric Liquid Crystals: A Unique State of Matter; in: Advances in the Synthesis and Reactivity of Solids; Mallouk, T.E., Ed.; JAI Press Ltd: Greenwich, Connecticut, 1991; Vol.1, pp 173–235.Google Scholar
10 Glaser, M. A.; Ginzburg, V. V.; Clark, N. A.; Garcia, E.; Walba, D. M.; Malzbender, R. Molecular Physics Reports 1995, 10, 26–47.Google Scholar
11 The properties of this material have been reported in detail: (a) Walba, D.M.; Ros, M.B.; Clark, N.A.; Shao, R.; Johnson, K.M.; Robinson, M.G.; Liu, J.Y.; Doroski, D., in Materials for Nonlinear Optics: Chemical Perspectives, Stucky, G.D., Ed.; Americal Chemical Society, Washington DC, 1991; pp 484. (b) Walba, D.M.; Ros, M.B.; Clark, N.A.; Shao, R.; Robinson, M.G.; Liu, J.Y.; Johnson, K.M.; Doroski, D. J. Am. Chem. Soc. 1991, 113, 5471.Google Scholar
12 A PNA derivative developed at Roche (see reference 3b) exhibited a pe ≈. 10% when the dimethylamino group was situated ortho to the alkyloxy tail, while the flipped configuration yielded pe ≈ 30% (see reference la).Google Scholar
13 All new compounds reported herein showed consistent 1H and 13C NMR spectra, mass spectra, and gave satisfactory combustion analysis. The synthesis of these compounds will be reported elsewhere.Google Scholar
14 A dipole moment of 5.7 Debye perpindicular to the director was calculated for compound 1 using MOPAC and AM I parameters. The observed P yields a ferroelectric dipole density of 0.5 D/molecule along fi, suggesting a 9% polar excess. A dipole moment of 9.2 Debye perpindicular to the director was calculated for compound 2. The observed P yields a dipole density of 2.0 D/molecule along , suggesting a 22% polar excess.Google Scholar