Abstract

Improved nonlinear organic chromophores of varying conjugation length with either thiobarbituric acid or 3-dicyanomethylene-2,3-dihydrobenzothiophene-1,1-dioxide (FORON<sup>®</sup> 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<sup>−48</sup> 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).
  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).
  3. V. P. Rao, A. K-Y. Jen, K. Y. Wong, and K. J. Drost, J. Chem. Soc. Chem. Commun. 1118–1120(1993).
  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).
  5. FORON® Blue is a registered trademark of SANDOZ Ltd., Basel, Switzerland.
  6. British Patent GB 2026528 (1980); French Patent Fr 2438045 (1980). Both are held by Sandoz Ltd. (inventor, W. Baumann).
  7. B. Levine and C. Bethea, Appl. Phys. Lett. 24, 445(1974).
  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. SPIE 2025, 192 (1993).
  9. L. Cheng, W. Tam, G. Meredith, G. Rikken, and E. Meijer, Nonlinear Optical Properties of Organic Materials II, G. Khanarian, ed., Proc. SPIE 1147, 61 (1990).
  10. A. Willetts, J. E. Rice, D. M. Burland, and D. P. Shelton, J. Chem. Phys. 97, 7590(1992).
  11. S. Akiyama, K. Nakashima, S. Nakatsuji, M. Suzuki, and C. Umekawa, Dyes Pigm. 8, 459 (1987).
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  13. C. W. Spangler and R. K. McCoy, Synth. Commun. 18, 51 (1988).
  14. M. Ahlheim and F. Lehr, Macromol. Chem. Phys. 195, 361 (1994).
  15. C. C. Teng and H. T. Man, Appl. Phys. Lett. 56, 1734(1990).
  16. J.-L. Oudar, J. Chem. Phys. 67, 446(1977).
  17. B. F. Levine and C. G. Bethea, J. Chem. Phys. 63, 2666(1975).
  18. I. Ledoux and J. Zyss, Chem. Phys. 73, 203(1982).
  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. SPIE 2025, 70 (1993).
  21. P. Prêtre, P. Kaatz, A. Bohren, P. Günter, B. Zysset, M. Ahlheim, M. Stähelin, and F. Lehr, Macromolecules 27, 5476(1994).
  22. K. D. Singer, M. G. Kuzyk, and J. E. Sohn, J. Opt. Soc. Am. B 4, 968(1987).
  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.

1996

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).

1994

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).

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

1993

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).

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

1992

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

1990

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

1987

1982

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

1977

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

1975

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

1974

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

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).

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

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).

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).

Bethea, C.

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

Bethea, C. G.

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

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).

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).

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).

Bohren, A.

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

Burland, D. M.

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

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).

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).

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).

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).

Günter, P.

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

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).

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).

Kaatz, P.

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

Kuzyk, M. G.

Ledoux, I.

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

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).

Lehr, F.

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

Levine, B.

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

Levine, B. F.

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

Man, H. T.

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

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).

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).

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).

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).

Oudar, J.-L.

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

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).

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).

Prêtre, P.

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

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).

Rice, J. E.

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

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).

Shelton, D. P.

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

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).

Sohn, J. E.

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).

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

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).

Teng, C. C.

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

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).

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).

Willetts, A.

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

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).

Zyss, J.

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

Zysset, B.

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).

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

Appl. Phys. Lett.

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

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

Chem. Phys.

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

J. Am. Chem. Soc.

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).

J. Chem. Phys.

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

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

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

J. Chem. Soc. Chem. Commun.

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

J. Opt. Soc. Am. B

Macromolecules

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

Science

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).

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).

Other

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

British Patent GB 2026528 (1980); French Patent Fr 2438045 (1980). Both are held by Sandoz Ltd. (inventor, W. Baumann).

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

R. Lemke, Synthesis (May 1974), p. 359.

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

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

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.

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

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. SPIE 2025, 70 (1993).

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. SPIE 2025, 192 (1993).

L. Cheng, W. Tam, G. Meredith, G. Rikken, and E. Meijer, Nonlinear Optical Properties of Organic Materials II, G. Khanarian, ed., Proc. SPIE 1147, 61 (1990).

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