Abstract

Improved nonlinear organic chromophores of varying conjugation length with either thiobarbituric acid or 3-dicyanomethylene-2,3-dihydrobenzothiophene-1,1-dioxide (FORON® Blue) acceptors have been synthesized and investigated for their nonlinear optical properties. Very large quadratic hyperpolarizabilities β(-2ω;ω,ω) have been found, up to 25,700×10-48 esu at λ=1.91 µm. In a guest–host polymer very high electro-optic (EO) coefficients, of up to 55 pm/V, have been determined at λ=1.31 µm with 20-wt % chromophore loading. We find good agreement between molecular parameters evaluated by electric-field-induced second-harmonic generation (EFISH) and the measurements of guest–host solid–solid solutions. The latter method is well suited to the determination of the product of dipole moment μ and hyperpolarizability β quickly and reliably at the wavelength of interest for EO applications without the complications associated with EFISH measurements.

© 1996 Optical Society of America

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  1. S. R. Marder, L.-T. Cheng, B. G. Tiemann, A. C. Friedli, M. Blanchard-Desce, J. W. Perry, and J. Skindhøj, Science 263, 511 (1994).
    [CrossRef] [PubMed]
  2. C. R. Moylan, R. J. Twieg, V. Y. Lee, S. A. Swanson, K. M. Betterton, and R. D. Miller, J. Am. Chem. Soc. 115, 12599 (1993).
    [CrossRef]
  3. V. P. Rao, A. K-Y. Jen, K. Y. Wong, and K. J. Drost, J. Chem. Soc. Chem. Commun.1118–1120 (1993).
    [CrossRef]
  4. M. Ahlheim, M. Barzoukas, P. V. Bedworth, M. Blanchard-Desce, A. Fort, Z.-Y. Hu, S. R. Marder, J. W. Perry, C. Runser, M. Stähelin, and B. Zysset, Science 271, 335 (1996).
    [CrossRef]
  5. FORON® Blue is a registered trademark of SANDOZ Ltd., Basel, Switzerland.
  6. British PatentGB 2026528 (1980); French PatentFr 2438045 (1980). Both are held by Sandoz Ltd. (inventor, W. Baumann).
  7. B. Levine and C. Bethea, Appl. Phys. Lett. 24, 445 (1974).
    [CrossRef]
  8. C. R. Moylan, S. A. Swanson, C. A. Walsh, J. I. Thackara, R. J. Twieg, R. D. Miller, and V. Y. Lee, in Nonlinear Optical Properties of Organic Materials VI, G. R. Möhlmann, ed., Proc. SPIE2025, 192 (1993).
    [CrossRef]
  9. L. Cheng, W. Tam, G. Meredith, G. Rikken, and E. Meijer, Nonlinear Optical Properties of Organic Materials II, G. Khanarian, ed., Proc. SPIE1147, 61 (1990).
    [CrossRef]
  10. A. Willetts, J. E. Rice, D. M. Burland, and D. P. Shelton, J. Chem. Phys. 97, 7590 (1992).
    [CrossRef]
  11. S. Akiyama, K. Nakashima, S. Nakatsuji, M. Suzuki, and C. Umekawa, Dyes Pigm. 8, 459 (1987).
    [CrossRef]
  12. R. Lemke, Synthesis (May1974), p. 359.
    [CrossRef]
  13. C. W. Spangler and R. K. McCoy, Synth. Commun. 18, 51 (1988).
    [CrossRef]
  14. M. Ahlheim and F. Lehr, Macromol. Chem. Phys. 195, 361 (1994).
    [CrossRef]
  15. C. C. Teng and H. T. Man, Appl. Phys. Lett. 56, 1734 (1990).
    [CrossRef]
  16. J.-L. Oudar, J. Chem. Phys. 67, 446 (1977).
    [CrossRef]
  17. B. F. Levine and C. G. Bethea, J. Chem. Phys. 63, 2666 (1975).
    [CrossRef]
  18. I. Ledoux and J. Zyss, Chem. Phys. 73, 203 (1982).
    [CrossRef]
  19. J. Messier, F. Kajzar, C. Sentheim, M. Barzoukas, J. Zyss, M. Blanchard-Desce, and J. Lehn, Nonlinear Opt. 2, 53 (1992).
  20. B. Zysset, M. Ahlheim, M. Stähelin, F. Lehr, P. Prêtre, P. Kaatz, and P. Günter, in Nonlinear Optical Properties of Organic Materials VI, G. R. Möhlmann, ed., Proc. SPIE2025, 70 (1993).
    [CrossRef]
  21. P. Prêtre, P. Kaatz, A. Bohren, P. Günter, B. Zysset, M. Ahlheim, M. Stähelin, and F. Lehr, Macromolecules 27, 5476 (1994).
    [CrossRef]
  22. K. D. Singer, M. G. Kuzyk, and J. E. Sohn, J. Opt. Soc. Am. B 4, 968 (1987).
    [CrossRef]
  23. J. Zyss and D. Chemla, in Nonlinear Optical Properties of Organic Molecules and Crystals, Vol. 1 of Quadratic Nonlinear Optics, D. S. Chemla and J. Zyss, eds. (Academic, New York, 1987), p. 23.
    [CrossRef]

1996 (1)

M. Ahlheim, M. Barzoukas, P. V. Bedworth, M. Blanchard-Desce, A. Fort, Z.-Y. Hu, S. R. Marder, J. W. Perry, C. Runser, M. Stähelin, and B. Zysset, Science 271, 335 (1996).
[CrossRef]

1994 (3)

S. R. Marder, L.-T. Cheng, B. G. Tiemann, A. C. Friedli, M. Blanchard-Desce, J. W. Perry, and J. Skindhøj, Science 263, 511 (1994).
[CrossRef] [PubMed]

M. Ahlheim and F. Lehr, Macromol. Chem. Phys. 195, 361 (1994).
[CrossRef]

P. Prêtre, P. Kaatz, A. Bohren, P. Günter, B. Zysset, M. Ahlheim, M. Stähelin, and F. Lehr, Macromolecules 27, 5476 (1994).
[CrossRef]

1993 (2)

C. R. Moylan, R. J. Twieg, V. Y. Lee, S. A. Swanson, K. M. Betterton, and R. D. Miller, J. Am. Chem. Soc. 115, 12599 (1993).
[CrossRef]

V. P. Rao, A. K-Y. Jen, K. Y. Wong, and K. J. Drost, J. Chem. Soc. Chem. Commun.1118–1120 (1993).
[CrossRef]

1992 (2)

J. Messier, F. Kajzar, C. Sentheim, M. Barzoukas, J. Zyss, M. Blanchard-Desce, and J. Lehn, Nonlinear Opt. 2, 53 (1992).

A. Willetts, J. E. Rice, D. M. Burland, and D. P. Shelton, J. Chem. Phys. 97, 7590 (1992).
[CrossRef]

1990 (1)

C. C. Teng and H. T. Man, Appl. Phys. Lett. 56, 1734 (1990).
[CrossRef]

1988 (1)

C. W. Spangler and R. K. McCoy, Synth. Commun. 18, 51 (1988).
[CrossRef]

1987 (2)

S. Akiyama, K. Nakashima, S. Nakatsuji, M. Suzuki, and C. Umekawa, Dyes Pigm. 8, 459 (1987).
[CrossRef]

K. D. Singer, M. G. Kuzyk, and J. E. Sohn, J. Opt. Soc. Am. B 4, 968 (1987).
[CrossRef]

1982 (1)

I. Ledoux and J. Zyss, Chem. Phys. 73, 203 (1982).
[CrossRef]

1977 (1)

J.-L. Oudar, J. Chem. Phys. 67, 446 (1977).
[CrossRef]

1975 (1)

B. F. Levine and C. G. Bethea, J. Chem. Phys. 63, 2666 (1975).
[CrossRef]

1974 (2)

B. Levine and C. Bethea, Appl. Phys. Lett. 24, 445 (1974).
[CrossRef]

R. Lemke, Synthesis (May1974), p. 359.
[CrossRef]

Ahlheim, M.

M. Ahlheim, M. Barzoukas, P. V. Bedworth, M. Blanchard-Desce, A. Fort, Z.-Y. Hu, S. R. Marder, J. W. Perry, C. Runser, M. Stähelin, and B. Zysset, Science 271, 335 (1996).
[CrossRef]

P. Prêtre, P. Kaatz, A. Bohren, P. Günter, B. Zysset, M. Ahlheim, M. Stähelin, and F. Lehr, Macromolecules 27, 5476 (1994).
[CrossRef]

M. Ahlheim and F. Lehr, Macromol. Chem. Phys. 195, 361 (1994).
[CrossRef]

B. Zysset, M. Ahlheim, M. Stähelin, F. Lehr, P. Prêtre, P. Kaatz, and P. Günter, in Nonlinear Optical Properties of Organic Materials VI, G. R. Möhlmann, ed., Proc. SPIE2025, 70 (1993).
[CrossRef]

Akiyama, S.

S. Akiyama, K. Nakashima, S. Nakatsuji, M. Suzuki, and C. Umekawa, Dyes Pigm. 8, 459 (1987).
[CrossRef]

Barzoukas, M.

M. Ahlheim, M. Barzoukas, P. V. Bedworth, M. Blanchard-Desce, A. Fort, Z.-Y. Hu, S. R. Marder, J. W. Perry, C. Runser, M. Stähelin, and B. Zysset, Science 271, 335 (1996).
[CrossRef]

J. Messier, F. Kajzar, C. Sentheim, M. Barzoukas, J. Zyss, M. Blanchard-Desce, and J. Lehn, Nonlinear Opt. 2, 53 (1992).

Bedworth, P. V.

M. Ahlheim, M. Barzoukas, P. V. Bedworth, M. Blanchard-Desce, A. Fort, Z.-Y. Hu, S. R. Marder, J. W. Perry, C. Runser, M. Stähelin, and B. Zysset, Science 271, 335 (1996).
[CrossRef]

Bethea, C.

B. Levine and C. Bethea, Appl. Phys. Lett. 24, 445 (1974).
[CrossRef]

Bethea, C. G.

B. F. Levine and C. G. Bethea, J. Chem. Phys. 63, 2666 (1975).
[CrossRef]

Betterton, K. M.

C. R. Moylan, R. J. Twieg, V. Y. Lee, S. A. Swanson, K. M. Betterton, and R. D. Miller, J. Am. Chem. Soc. 115, 12599 (1993).
[CrossRef]

Blanchard-Desce, M.

M. Ahlheim, M. Barzoukas, P. V. Bedworth, M. Blanchard-Desce, A. Fort, Z.-Y. Hu, S. R. Marder, J. W. Perry, C. Runser, M. Stähelin, and B. Zysset, Science 271, 335 (1996).
[CrossRef]

S. R. Marder, L.-T. Cheng, B. G. Tiemann, A. C. Friedli, M. Blanchard-Desce, J. W. Perry, and J. Skindhøj, Science 263, 511 (1994).
[CrossRef] [PubMed]

J. Messier, F. Kajzar, C. Sentheim, M. Barzoukas, J. Zyss, M. Blanchard-Desce, and J. Lehn, Nonlinear Opt. 2, 53 (1992).

Bohren, A.

P. Prêtre, P. Kaatz, A. Bohren, P. Günter, B. Zysset, M. Ahlheim, M. Stähelin, and F. Lehr, Macromolecules 27, 5476 (1994).
[CrossRef]

Burland, D. M.

A. Willetts, J. E. Rice, D. M. Burland, and D. P. Shelton, J. Chem. Phys. 97, 7590 (1992).
[CrossRef]

Chemla, D.

J. Zyss and D. Chemla, in Nonlinear Optical Properties of Organic Molecules and Crystals, Vol. 1 of Quadratic Nonlinear Optics, D. S. Chemla and J. Zyss, eds. (Academic, New York, 1987), p. 23.
[CrossRef]

Cheng, L.

L. Cheng, W. Tam, G. Meredith, G. Rikken, and E. Meijer, Nonlinear Optical Properties of Organic Materials II, G. Khanarian, ed., Proc. SPIE1147, 61 (1990).
[CrossRef]

Cheng, L.-T.

S. R. Marder, L.-T. Cheng, B. G. Tiemann, A. C. Friedli, M. Blanchard-Desce, J. W. Perry, and J. Skindhøj, Science 263, 511 (1994).
[CrossRef] [PubMed]

Drost, K. J.

V. P. Rao, A. K-Y. Jen, K. Y. Wong, and K. J. Drost, J. Chem. Soc. Chem. Commun.1118–1120 (1993).
[CrossRef]

Fort, A.

M. Ahlheim, M. Barzoukas, P. V. Bedworth, M. Blanchard-Desce, A. Fort, Z.-Y. Hu, S. R. Marder, J. W. Perry, C. Runser, M. Stähelin, and B. Zysset, Science 271, 335 (1996).
[CrossRef]

Friedli, A. C.

S. R. Marder, L.-T. Cheng, B. G. Tiemann, A. C. Friedli, M. Blanchard-Desce, J. W. Perry, and J. Skindhøj, Science 263, 511 (1994).
[CrossRef] [PubMed]

Günter, P.

P. Prêtre, P. Kaatz, A. Bohren, P. Günter, B. Zysset, M. Ahlheim, M. Stähelin, and F. Lehr, Macromolecules 27, 5476 (1994).
[CrossRef]

B. Zysset, M. Ahlheim, M. Stähelin, F. Lehr, P. Prêtre, P. Kaatz, and P. Günter, in Nonlinear Optical Properties of Organic Materials VI, G. R. Möhlmann, ed., Proc. SPIE2025, 70 (1993).
[CrossRef]

Hu, Z.-Y.

M. Ahlheim, M. Barzoukas, P. V. Bedworth, M. Blanchard-Desce, A. Fort, Z.-Y. Hu, S. R. Marder, J. W. Perry, C. Runser, M. Stähelin, and B. Zysset, Science 271, 335 (1996).
[CrossRef]

Jen, A. K-Y.

V. P. Rao, A. K-Y. Jen, K. Y. Wong, and K. J. Drost, J. Chem. Soc. Chem. Commun.1118–1120 (1993).
[CrossRef]

Kaatz, P.

P. Prêtre, P. Kaatz, A. Bohren, P. Günter, B. Zysset, M. Ahlheim, M. Stähelin, and F. Lehr, Macromolecules 27, 5476 (1994).
[CrossRef]

B. Zysset, M. Ahlheim, M. Stähelin, F. Lehr, P. Prêtre, P. Kaatz, and P. Günter, in Nonlinear Optical Properties of Organic Materials VI, G. R. Möhlmann, ed., Proc. SPIE2025, 70 (1993).
[CrossRef]

Kajzar, F.

J. Messier, F. Kajzar, C. Sentheim, M. Barzoukas, J. Zyss, M. Blanchard-Desce, and J. Lehn, Nonlinear Opt. 2, 53 (1992).

Kuzyk, M. G.

Ledoux, I.

I. Ledoux and J. Zyss, Chem. Phys. 73, 203 (1982).
[CrossRef]

Lee, V. Y.

C. R. Moylan, R. J. Twieg, V. Y. Lee, S. A. Swanson, K. M. Betterton, and R. D. Miller, J. Am. Chem. Soc. 115, 12599 (1993).
[CrossRef]

C. R. Moylan, S. A. Swanson, C. A. Walsh, J. I. Thackara, R. J. Twieg, R. D. Miller, and V. Y. Lee, in Nonlinear Optical Properties of Organic Materials VI, G. R. Möhlmann, ed., Proc. SPIE2025, 192 (1993).
[CrossRef]

Lehn, J.

J. Messier, F. Kajzar, C. Sentheim, M. Barzoukas, J. Zyss, M. Blanchard-Desce, and J. Lehn, Nonlinear Opt. 2, 53 (1992).

Lehr, F.

M. Ahlheim and F. Lehr, Macromol. Chem. Phys. 195, 361 (1994).
[CrossRef]

P. Prêtre, P. Kaatz, A. Bohren, P. Günter, B. Zysset, M. Ahlheim, M. Stähelin, and F. Lehr, Macromolecules 27, 5476 (1994).
[CrossRef]

B. Zysset, M. Ahlheim, M. Stähelin, F. Lehr, P. Prêtre, P. Kaatz, and P. Günter, in Nonlinear Optical Properties of Organic Materials VI, G. R. Möhlmann, ed., Proc. SPIE2025, 70 (1993).
[CrossRef]

Lemke, R.

R. Lemke, Synthesis (May1974), p. 359.
[CrossRef]

Levine, B.

B. Levine and C. Bethea, Appl. Phys. Lett. 24, 445 (1974).
[CrossRef]

Levine, B. F.

B. F. Levine and C. G. Bethea, J. Chem. Phys. 63, 2666 (1975).
[CrossRef]

Man, H. T.

C. C. Teng and H. T. Man, Appl. Phys. Lett. 56, 1734 (1990).
[CrossRef]

Marder, S. R.

M. Ahlheim, M. Barzoukas, P. V. Bedworth, M. Blanchard-Desce, A. Fort, Z.-Y. Hu, S. R. Marder, J. W. Perry, C. Runser, M. Stähelin, and B. Zysset, Science 271, 335 (1996).
[CrossRef]

S. R. Marder, L.-T. Cheng, B. G. Tiemann, A. C. Friedli, M. Blanchard-Desce, J. W. Perry, and J. Skindhøj, Science 263, 511 (1994).
[CrossRef] [PubMed]

McCoy, R. K.

C. W. Spangler and R. K. McCoy, Synth. Commun. 18, 51 (1988).
[CrossRef]

Meijer, E.

L. Cheng, W. Tam, G. Meredith, G. Rikken, and E. Meijer, Nonlinear Optical Properties of Organic Materials II, G. Khanarian, ed., Proc. SPIE1147, 61 (1990).
[CrossRef]

Meredith, G.

L. Cheng, W. Tam, G. Meredith, G. Rikken, and E. Meijer, Nonlinear Optical Properties of Organic Materials II, G. Khanarian, ed., Proc. SPIE1147, 61 (1990).
[CrossRef]

Messier, J.

J. Messier, F. Kajzar, C. Sentheim, M. Barzoukas, J. Zyss, M. Blanchard-Desce, and J. Lehn, Nonlinear Opt. 2, 53 (1992).

Miller, R. D.

C. R. Moylan, R. J. Twieg, V. Y. Lee, S. A. Swanson, K. M. Betterton, and R. D. Miller, J. Am. Chem. Soc. 115, 12599 (1993).
[CrossRef]

C. R. Moylan, S. A. Swanson, C. A. Walsh, J. I. Thackara, R. J. Twieg, R. D. Miller, and V. Y. Lee, in Nonlinear Optical Properties of Organic Materials VI, G. R. Möhlmann, ed., Proc. SPIE2025, 192 (1993).
[CrossRef]

Moylan, C. R.

C. R. Moylan, R. J. Twieg, V. Y. Lee, S. A. Swanson, K. M. Betterton, and R. D. Miller, J. Am. Chem. Soc. 115, 12599 (1993).
[CrossRef]

C. R. Moylan, S. A. Swanson, C. A. Walsh, J. I. Thackara, R. J. Twieg, R. D. Miller, and V. Y. Lee, in Nonlinear Optical Properties of Organic Materials VI, G. R. Möhlmann, ed., Proc. SPIE2025, 192 (1993).
[CrossRef]

Nakashima, K.

S. Akiyama, K. Nakashima, S. Nakatsuji, M. Suzuki, and C. Umekawa, Dyes Pigm. 8, 459 (1987).
[CrossRef]

Nakatsuji, S.

S. Akiyama, K. Nakashima, S. Nakatsuji, M. Suzuki, and C. Umekawa, Dyes Pigm. 8, 459 (1987).
[CrossRef]

Oudar, J.-L.

J.-L. Oudar, J. Chem. Phys. 67, 446 (1977).
[CrossRef]

Perry, J. W.

M. Ahlheim, M. Barzoukas, P. V. Bedworth, M. Blanchard-Desce, A. Fort, Z.-Y. Hu, S. R. Marder, J. W. Perry, C. Runser, M. Stähelin, and B. Zysset, Science 271, 335 (1996).
[CrossRef]

S. R. Marder, L.-T. Cheng, B. G. Tiemann, A. C. Friedli, M. Blanchard-Desce, J. W. Perry, and J. Skindhøj, Science 263, 511 (1994).
[CrossRef] [PubMed]

Prêtre, P.

P. Prêtre, P. Kaatz, A. Bohren, P. Günter, B. Zysset, M. Ahlheim, M. Stähelin, and F. Lehr, Macromolecules 27, 5476 (1994).
[CrossRef]

B. Zysset, M. Ahlheim, M. Stähelin, F. Lehr, P. Prêtre, P. Kaatz, and P. Günter, in Nonlinear Optical Properties of Organic Materials VI, G. R. Möhlmann, ed., Proc. SPIE2025, 70 (1993).
[CrossRef]

Rao, V. P.

V. P. Rao, A. K-Y. Jen, K. Y. Wong, and K. J. Drost, J. Chem. Soc. Chem. Commun.1118–1120 (1993).
[CrossRef]

Rice, J. E.

A. Willetts, J. E. Rice, D. M. Burland, and D. P. Shelton, J. Chem. Phys. 97, 7590 (1992).
[CrossRef]

Rikken, G.

L. Cheng, W. Tam, G. Meredith, G. Rikken, and E. Meijer, Nonlinear Optical Properties of Organic Materials II, G. Khanarian, ed., Proc. SPIE1147, 61 (1990).
[CrossRef]

Runser, C.

M. Ahlheim, M. Barzoukas, P. V. Bedworth, M. Blanchard-Desce, A. Fort, Z.-Y. Hu, S. R. Marder, J. W. Perry, C. Runser, M. Stähelin, and B. Zysset, Science 271, 335 (1996).
[CrossRef]

Sentheim, C.

J. Messier, F. Kajzar, C. Sentheim, M. Barzoukas, J. Zyss, M. Blanchard-Desce, and J. Lehn, Nonlinear Opt. 2, 53 (1992).

Shelton, D. P.

A. Willetts, J. E. Rice, D. M. Burland, and D. P. Shelton, J. Chem. Phys. 97, 7590 (1992).
[CrossRef]

Singer, K. D.

Skindhøj, J.

S. R. Marder, L.-T. Cheng, B. G. Tiemann, A. C. Friedli, M. Blanchard-Desce, J. W. Perry, and J. Skindhøj, Science 263, 511 (1994).
[CrossRef] [PubMed]

Sohn, J. E.

Spangler, C. W.

C. W. Spangler and R. K. McCoy, Synth. Commun. 18, 51 (1988).
[CrossRef]

Stähelin, M.

M. Ahlheim, M. Barzoukas, P. V. Bedworth, M. Blanchard-Desce, A. Fort, Z.-Y. Hu, S. R. Marder, J. W. Perry, C. Runser, M. Stähelin, and B. Zysset, Science 271, 335 (1996).
[CrossRef]

P. Prêtre, P. Kaatz, A. Bohren, P. Günter, B. Zysset, M. Ahlheim, M. Stähelin, and F. Lehr, Macromolecules 27, 5476 (1994).
[CrossRef]

B. Zysset, M. Ahlheim, M. Stähelin, F. Lehr, P. Prêtre, P. Kaatz, and P. Günter, in Nonlinear Optical Properties of Organic Materials VI, G. R. Möhlmann, ed., Proc. SPIE2025, 70 (1993).
[CrossRef]

Suzuki, M.

S. Akiyama, K. Nakashima, S. Nakatsuji, M. Suzuki, and C. Umekawa, Dyes Pigm. 8, 459 (1987).
[CrossRef]

Swanson, S. A.

C. R. Moylan, R. J. Twieg, V. Y. Lee, S. A. Swanson, K. M. Betterton, and R. D. Miller, J. Am. Chem. Soc. 115, 12599 (1993).
[CrossRef]

C. R. Moylan, S. A. Swanson, C. A. Walsh, J. I. Thackara, R. J. Twieg, R. D. Miller, and V. Y. Lee, in Nonlinear Optical Properties of Organic Materials VI, G. R. Möhlmann, ed., Proc. SPIE2025, 192 (1993).
[CrossRef]

Tam, W.

L. Cheng, W. Tam, G. Meredith, G. Rikken, and E. Meijer, Nonlinear Optical Properties of Organic Materials II, G. Khanarian, ed., Proc. SPIE1147, 61 (1990).
[CrossRef]

Teng, C. C.

C. C. Teng and H. T. Man, Appl. Phys. Lett. 56, 1734 (1990).
[CrossRef]

Thackara, J. I.

C. R. Moylan, S. A. Swanson, C. A. Walsh, J. I. Thackara, R. J. Twieg, R. D. Miller, and V. Y. Lee, in Nonlinear Optical Properties of Organic Materials VI, G. R. Möhlmann, ed., Proc. SPIE2025, 192 (1993).
[CrossRef]

Tiemann, B. G.

S. R. Marder, L.-T. Cheng, B. G. Tiemann, A. C. Friedli, M. Blanchard-Desce, J. W. Perry, and J. Skindhøj, Science 263, 511 (1994).
[CrossRef] [PubMed]

Twieg, R. J.

C. R. Moylan, R. J. Twieg, V. Y. Lee, S. A. Swanson, K. M. Betterton, and R. D. Miller, J. Am. Chem. Soc. 115, 12599 (1993).
[CrossRef]

C. R. Moylan, S. A. Swanson, C. A. Walsh, J. I. Thackara, R. J. Twieg, R. D. Miller, and V. Y. Lee, in Nonlinear Optical Properties of Organic Materials VI, G. R. Möhlmann, ed., Proc. SPIE2025, 192 (1993).
[CrossRef]

Umekawa, C.

S. Akiyama, K. Nakashima, S. Nakatsuji, M. Suzuki, and C. Umekawa, Dyes Pigm. 8, 459 (1987).
[CrossRef]

Walsh, C. A.

C. R. Moylan, S. A. Swanson, C. A. Walsh, J. I. Thackara, R. J. Twieg, R. D. Miller, and V. Y. Lee, in Nonlinear Optical Properties of Organic Materials VI, G. R. Möhlmann, ed., Proc. SPIE2025, 192 (1993).
[CrossRef]

Willetts, A.

A. Willetts, J. E. Rice, D. M. Burland, and D. P. Shelton, J. Chem. Phys. 97, 7590 (1992).
[CrossRef]

Wong, K. Y.

V. P. Rao, A. K-Y. Jen, K. Y. Wong, and K. J. Drost, J. Chem. Soc. Chem. Commun.1118–1120 (1993).
[CrossRef]

Zyss, J.

J. Messier, F. Kajzar, C. Sentheim, M. Barzoukas, J. Zyss, M. Blanchard-Desce, and J. Lehn, Nonlinear Opt. 2, 53 (1992).

I. Ledoux and J. Zyss, Chem. Phys. 73, 203 (1982).
[CrossRef]

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FORON® Blue is a registered trademark of SANDOZ Ltd., Basel, Switzerland.

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[CrossRef]

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Figures (8)

Fig. 1
Fig. 1

Structure and route of synthesis of push–pull polyenes with thiobarbituric acid (TBA) and 3-dicyanomethylene-2,3-dihydrobenzothiophene-1,1-dioxide (FB) acceptors. R denotes C2H5 (5a), C2H5 (7a), C6H5 (7b), C2H5 (9a), C6H5 (9b), C2H5 (11a), and C6H5 (11b).

Fig. 2
Fig. 2

Highly soluble di-n-buthyl analog of molecule 10 in Fig. 1.

Fig. 3
Fig. 3

Structure of the chromophore Azo 1̲.

Fig. 4
Fig. 4

Structure of the side-chain polymer containing Azo chromophores.

Fig. 5
Fig. 5

Experimental setup for the electro-optic (EO) characterization of guest–host films.

Fig. 6
Fig. 6

EO coefficient at λ=1.313 µm versus chromophore loading of polycarbonate (PC) guest–host polymers.

Fig. 7
Fig. 7

EO coefficient versus poling field E of a guest–host polymer (11-wt % of molecule 6 dissolved in PC, with λ=1.313 µm).

Fig. 8
Fig. 8

Log–log plot of µβ(-ω;ω,0) versus absorption maximum λmax. All data are from EO measurements at λ=1.313 µm and normalized to the value of the chromophore Azo 1̲.

Tables (4)

Tables Icon

Table 1 Results of Electro-Optical (EO) Measurements on Guest–Host Films Containing the Chromophore Azo 1̲ and Comparison with EO Measurements on the Azo-Containing Side-Chain Polymer (λ=1.31 µm)

Tables Icon

Table 2 Measured r-Values of PC–Guest–Host Thin Films Measured at λ=1.31 µma

Tables Icon

Table 3 Nonlinear Optical Properties of Polyenes with Thiobarbituric Acid (TBA) as Acceptor

Tables Icon

Table 4 Nonlinear Optical Properties of Novel Polyenes with 3-Dicyanomethylene-2,3-Dihydrobenzothiopene-1,1-Dioxide (FB) as Acceptor

Equations (6)

Equations on this page are rendered with MathJax. Learn more.

γ0=γe(-2ω;ω,ω,0)+μβ(-2ω;ω,ω)5kT,
βi(2ω)=jβijj(2ω).
r33=2Nfμβ(-ω;ω,ω,0)5kTn4E,
μβ(-ω;ω,0)relative=μβ(-2ω;ω,ω)(μβ)7a(-2ω;ω,ω)fEOfEFISH.
fEO=[1-(λmax,PC7a)2/λ2]23-(λmax,PC7a)2/λ23-λmax,PC2/λ2[1-(λmax,PC)2/λ2]2.
fEFISH=1-(λmax,solv)2/λ21-(λmax,solv7a)2/λ21-4(λmax,solv)2/λ21-4(λmax,solv7a)2/λ2.

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