Abstract

Single crystals of 4-dimethylaminobenzaldehyde-4-nitrophenylhydrazone were grown from solution. We determined their linear-optical (absorption and refractive indices) as well as their nonlinear-optical properties. From the highest nonlinear-optical coefficient d12=270 pm/V at λ=1.542 μm we determine an effective nonlinear-optical coefficient deff≥150 pm/V for phase-matched frequency doubling that is, to the best of our knowledge, the largest reported phase-matchable coefficient. The nonlinear-optical properties are discussed in terms of the crystal structure and the molecular hyperpolarizabilities. In addition, the phase-matching configurations for second-harmonic generation and optic parametric oscillation are derived.

© 1997 Optical Society of America

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1996 (1)

F. Pan, C. Bosshard, M. S. Wong, C. Serbutoviez, S. Follonier, P. Günter, and K. Schenk, “Polymorphism, growth and characterization of a new organic nonlinear optical crystal: 4-dimethylaminobenzaldehyde-4-nitrophenylhydrazone (DANPH),” J. Cryst. Growth 165, 273–283 (1996).

1995 (4)

C. Bosshard, G. Knöpfle, P. Pre⁁tre, S. Follonier, C. Serbutoviez, and P. Günter, “Molecular crystals and polymers for nonlinear optics,” Opt. Eng. 34, 1951–1960 (1995).

C. Serbutoviez, C. Bosshard, G. Knöpfle, P. Wyss, P. Pre⁁tre, P. Günter, K. Schenk, E. Solari, and G. Chapuis, “Hydrazone derivatives, an efficient class of crystalline materials for nonlinear optics,” Chem. Mater. 7, 1198–1206 (1995).

G. Knöpfle, R. Schlesser, R. Ducret, and P. Günter, “Optical and nonlinear optical properties of 4′-dimethylamino-N-methyl-4-stilbazolium tosylate (DAST) crystals,” Nonlin. Opt. 9, 143–149 (1995).

D. E. Spence, S. Wielandy, C. L. Tang, C. Bosshard, and P. Günter, “High-repetition-rate femtosecond optical parametric oscillator based on KNbO3,” Opt. Lett. 20, 680–682 (1995).

1994 (1)

S. R. Marder, J. W. Perry, and C. P. Yakymyshyn, “Organic salts with large second-order optical nonlinearities,” Chem. Mater. 6, 1137–1147 (1994).

1993 (5)

1992 (2)

S. X. Dou, D. Josse, and J. Zyss, “Comparison of collinear and one-beam noncritical noncollinear phase matching in optical parametric amplification,” J. Opt. Soc. Am. B 9, 1312–1319 (1992).

D. A. Roberts, “Simplified characterization of uniaxial and biaxial nonlinear optical crystals: a plea for standardization of nomenclature and conventions,” IEEE J. Quantum Electron. 28, 2057–2074 (1992).

1991 (3)

C. Bubeck, A. Laschewsky, D. Lupo, D. Neher, P. Ottenbreit, W. Paulus, W. Prass, H. Ringsdorf, and G. Wegner, “Amphiphilic dyes for nonlinear optics: dependence of second harmonic generation on functional group substitution,” Adv. Mater. 3, 54–58 (1991).

J. W. Perry, S. R. Marder, K. J. Perry, E. T. Sleva, C. Yakymyshyn, K. R. Stewart, and E. P. Boden, “Organic salts with large electro-optic coefficients,” in Nonlinear Optical Properties of Organic Materials IV, K. D. Singer, ed., Proc. SPIE 1560, 302–309 (1991).

K. Sutter, G. Knöpfle, N. Saupper, J. Hulliger, P. Günter, and W. Petter, “Nonlinear-optical, optical, and crystallographic properties of N-(4-nitro-2-pyridinyl)-phenylalaninol,” J. Opt. Soc. Am. B 8, 1483–1490 (1991).

1990 (1)

I. Ledoux, C. Lepers, A. Périgaud, J. Badan, and J. Zyss, “Linear and nonlinear optical properties of N-4nitrophenyl-L-prolinol single crystals,” Opt. Commun. 80, 149–154 (1990).

1989 (5)

P. Kerkoc, M. Zgonik, C. Bosshard, K. Sutter, and P. Günter, “Optical and nonlinear optical properties of 4-(N, N-dimethylamino)-3-acetamidonitrobenzene single crystals,” Appl. Phys. Lett. 54, 2062–2064 (1989).

K. Sutter, C. Bosshard, L. Baraldi, and P. Günter, “Nonlinear optical and electro-optic properties of 2(N-prolinol)-5-nitropyridine (PNP) crystals,” AIP Conf. Proc. 103, 127–132 (1989), Sec. 2.1.

S. R. Marder, J. W. Perry, and W. P. Schaeffer, “Synthesis of organic salts with large second-order optical nonlinearities,” Science 245, 626–628 (1989).

B. Wyncke and F. Brehat, “Calculation of the effective second-order non-linear coefficients along the phase matching directions in acentric orthorhombic biaxial crystals,” J. Phys. B 22, 363–376 (1989).

F. Brehat and B. Wyncke, “Calculation of double-refraction walk-off angle along the phase-matching directions in non-linear biaxial crystals,” J. Phys. B 22, 1891–1898 (1989).

1988 (2)

K. Sutter, C. Bosshard, W. S. Wang, G. Surmely, and P. Günter, “Linear and nonlinear optical properties of 2(N-prolinol)-5-nitropyridine,” Appl. Phys. Lett. 53, 1779–1781 (1988).

D. Lupo, W. Prass, U. Scheunemann, A. Laschewsky, H. Ringsdorf, and I. Ledoux, “Second-harmonic generation in Langmuir–Blodgett monolayers of stilbazium salt and phenylhydrazone dyes,” J. Opt. Soc. Am. B 5, 300–308 (1988).

1986 (1)

S. R. Hall, P. V. Kolinsky, R. Jones, S. Allen, P. Gordon, B. Bothwell, D. Bloor, P. A. Norman, M. Hursthouse, A. Karaulov, J. Baldwin, M. Goodyear, and D. Bishop, “Polymorphism and nonlinear optical activity in organic crystals,” J. Cryst. Growth 79, 745–751 (1986).

1982 (1)

J. Zyss and J. L. Oudar, “Relation between microscopic and macroscopic low-order optical nonlinearities of molecular crystals with one- or two-dimensional units,” Phys. Rev. A 26, 2028–2048 (1982).

1981 (1)

M. Sigelle and R. Hierle, “Determination of the electrooptic coefficients of 3-methyl 4-nitropyridine 1-oxide by an inter-ferometric phase modulation technique,” J. Appl. Phys. 52, 4199–4204 (1981).

1977 (1)

J. L. Oudar, “Optical nonlinearities of conjugated molecules. Stilbene derivatives and highly polar aromatics,” J. Chem. Phys. 67, 446–457 (1977).

1970 (1)

J. Jerphagnon and S. K. Kurtz, “Maker fringes: a detailed comparison of theory and experiment for isotropic and uniaxial crystals,” J. Appl. Phys. 41, 1667–1681 (1970).

1968 (1)

S. K. Kurtz and T. T. Perry, “A powder technique for the evaluation of nonlinear optical materials,” J. Appl. Phys. 39, 3798–3813 (1968).

1966 (1)

1913 (1)

L. Vecchiotto, “Ricerche sulli idrazoni,” Gazz. Chim. Ital. 43, 637–643 (1913).

Allen, S.

S. R. Hall, P. V. Kolinsky, R. Jones, S. Allen, P. Gordon, B. Bothwell, D. Bloor, P. A. Norman, M. Hursthouse, A. Karaulov, J. Baldwin, M. Goodyear, and D. Bishop, “Polymorphism and nonlinear optical activity in organic crystals,” J. Cryst. Growth 79, 745–751 (1986).

Assanto, G.

Badan, J.

I. Ledoux, C. Lepers, A. Périgaud, J. Badan, and J. Zyss, “Linear and nonlinear optical properties of N-4nitrophenyl-L-prolinol single crystals,” Opt. Commun. 80, 149–154 (1990).

Baldwin, J.

S. R. Hall, P. V. Kolinsky, R. Jones, S. Allen, P. Gordon, B. Bothwell, D. Bloor, P. A. Norman, M. Hursthouse, A. Karaulov, J. Baldwin, M. Goodyear, and D. Bishop, “Polymorphism and nonlinear optical activity in organic crystals,” J. Cryst. Growth 79, 745–751 (1986).

Baraldi, L.

K. Sutter, C. Bosshard, L. Baraldi, and P. Günter, “Nonlinear optical and electro-optic properties of 2(N-prolinol)-5-nitropyridine (PNP) crystals,” AIP Conf. Proc. 103, 127–132 (1989), Sec. 2.1.

Bishop, D.

S. R. Hall, P. V. Kolinsky, R. Jones, S. Allen, P. Gordon, B. Bothwell, D. Bloor, P. A. Norman, M. Hursthouse, A. Karaulov, J. Baldwin, M. Goodyear, and D. Bishop, “Polymorphism and nonlinear optical activity in organic crystals,” J. Cryst. Growth 79, 745–751 (1986).

Bloor, D.

S. R. Hall, P. V. Kolinsky, R. Jones, S. Allen, P. Gordon, B. Bothwell, D. Bloor, P. A. Norman, M. Hursthouse, A. Karaulov, J. Baldwin, M. Goodyear, and D. Bishop, “Polymorphism and nonlinear optical activity in organic crystals,” J. Cryst. Growth 79, 745–751 (1986).

Boden, E. P.

J. W. Perry, S. R. Marder, K. J. Perry, E. T. Sleva, C. Yakymyshyn, K. R. Stewart, and E. P. Boden, “Organic salts with large electro-optic coefficients,” in Nonlinear Optical Properties of Organic Materials IV, K. D. Singer, ed., Proc. SPIE 1560, 302–309 (1991).

Bosenberg, W. R.

Bosshard, C.

F. Pan, C. Bosshard, M. S. Wong, C. Serbutoviez, S. Follonier, P. Günter, and K. Schenk, “Polymorphism, growth and characterization of a new organic nonlinear optical crystal: 4-dimethylaminobenzaldehyde-4-nitrophenylhydrazone (DANPH),” J. Cryst. Growth 165, 273–283 (1996).

D. E. Spence, S. Wielandy, C. L. Tang, C. Bosshard, and P. Günter, “High-repetition-rate femtosecond optical parametric oscillator based on KNbO3,” Opt. Lett. 20, 680–682 (1995).

C. Serbutoviez, C. Bosshard, G. Knöpfle, P. Wyss, P. Pre⁁tre, P. Günter, K. Schenk, E. Solari, and G. Chapuis, “Hydrazone derivatives, an efficient class of crystalline materials for nonlinear optics,” Chem. Mater. 7, 1198–1206 (1995).

C. Bosshard, G. Knöpfle, P. Pre⁁tre, S. Follonier, C. Serbutoviez, and P. Günter, “Molecular crystals and polymers for nonlinear optics,” Opt. Eng. 34, 1951–1960 (1995).

K. Sutter, C. Bosshard, L. Baraldi, and P. Günter, “Nonlinear optical and electro-optic properties of 2(N-prolinol)-5-nitropyridine (PNP) crystals,” AIP Conf. Proc. 103, 127–132 (1989), Sec. 2.1.

P. Kerkoc, M. Zgonik, C. Bosshard, K. Sutter, and P. Günter, “Optical and nonlinear optical properties of 4-(N, N-dimethylamino)-3-acetamidonitrobenzene single crystals,” Appl. Phys. Lett. 54, 2062–2064 (1989).

K. Sutter, C. Bosshard, W. S. Wang, G. Surmely, and P. Günter, “Linear and nonlinear optical properties of 2(N-prolinol)-5-nitropyridine,” Appl. Phys. Lett. 53, 1779–1781 (1988).

Bothwell, B.

S. R. Hall, P. V. Kolinsky, R. Jones, S. Allen, P. Gordon, B. Bothwell, D. Bloor, P. A. Norman, M. Hursthouse, A. Karaulov, J. Baldwin, M. Goodyear, and D. Bishop, “Polymorphism and nonlinear optical activity in organic crystals,” J. Cryst. Growth 79, 745–751 (1986).

Brehat, F.

B. Wyncke and F. Brehat, “Calculation of the effective second-order non-linear coefficients along the phase matching directions in acentric orthorhombic biaxial crystals,” J. Phys. B 22, 363–376 (1989).

F. Brehat and B. Wyncke, “Calculation of double-refraction walk-off angle along the phase-matching directions in non-linear biaxial crystals,” J. Phys. B 22, 1891–1898 (1989).

Bubeck, C.

C. Bubeck, A. Laschewsky, D. Lupo, D. Neher, P. Ottenbreit, W. Paulus, W. Prass, H. Ringsdorf, and G. Wegner, “Amphiphilic dyes for nonlinear optics: dependence of second harmonic generation on functional group substitution,” Adv. Mater. 3, 54–58 (1991).

Chapuis, G.

C. Serbutoviez, C. Bosshard, G. Knöpfle, P. Wyss, P. Pre⁁tre, P. Günter, K. Schenk, E. Solari, and G. Chapuis, “Hydrazone derivatives, an efficient class of crystalline materials for nonlinear optics,” Chem. Mater. 7, 1198–1206 (1995).

Dou, S. X.

Ducret, R.

G. Knöpfle, R. Schlesser, R. Ducret, and P. Günter, “Optical and nonlinear optical properties of 4′-dimethylamino-N-methyl-4-stilbazolium tosylate (DAST) crystals,” Nonlin. Opt. 9, 143–149 (1995).

Follonier, S.

F. Pan, C. Bosshard, M. S. Wong, C. Serbutoviez, S. Follonier, P. Günter, and K. Schenk, “Polymorphism, growth and characterization of a new organic nonlinear optical crystal: 4-dimethylaminobenzaldehyde-4-nitrophenylhydrazone (DANPH),” J. Cryst. Growth 165, 273–283 (1996).

C. Bosshard, G. Knöpfle, P. Pre⁁tre, S. Follonier, C. Serbutoviez, and P. Günter, “Molecular crystals and polymers for nonlinear optics,” Opt. Eng. 34, 1951–1960 (1995).

Goodyear, M.

S. R. Hall, P. V. Kolinsky, R. Jones, S. Allen, P. Gordon, B. Bothwell, D. Bloor, P. A. Norman, M. Hursthouse, A. Karaulov, J. Baldwin, M. Goodyear, and D. Bishop, “Polymorphism and nonlinear optical activity in organic crystals,” J. Cryst. Growth 79, 745–751 (1986).

Gordon, P.

S. R. Hall, P. V. Kolinsky, R. Jones, S. Allen, P. Gordon, B. Bothwell, D. Bloor, P. A. Norman, M. Hursthouse, A. Karaulov, J. Baldwin, M. Goodyear, and D. Bishop, “Polymorphism and nonlinear optical activity in organic crystals,” J. Cryst. Growth 79, 745–751 (1986).

Günter, P.

F. Pan, C. Bosshard, M. S. Wong, C. Serbutoviez, S. Follonier, P. Günter, and K. Schenk, “Polymorphism, growth and characterization of a new organic nonlinear optical crystal: 4-dimethylaminobenzaldehyde-4-nitrophenylhydrazone (DANPH),” J. Cryst. Growth 165, 273–283 (1996).

C. Serbutoviez, C. Bosshard, G. Knöpfle, P. Wyss, P. Pre⁁tre, P. Günter, K. Schenk, E. Solari, and G. Chapuis, “Hydrazone derivatives, an efficient class of crystalline materials for nonlinear optics,” Chem. Mater. 7, 1198–1206 (1995).

D. E. Spence, S. Wielandy, C. L. Tang, C. Bosshard, and P. Günter, “High-repetition-rate femtosecond optical parametric oscillator based on KNbO3,” Opt. Lett. 20, 680–682 (1995).

C. Bosshard, G. Knöpfle, P. Pre⁁tre, S. Follonier, C. Serbutoviez, and P. Günter, “Molecular crystals and polymers for nonlinear optics,” Opt. Eng. 34, 1951–1960 (1995).

G. Knöpfle, R. Schlesser, R. Ducret, and P. Günter, “Optical and nonlinear optical properties of 4′-dimethylamino-N-methyl-4-stilbazolium tosylate (DAST) crystals,” Nonlin. Opt. 9, 143–149 (1995).

K. Sutter, G. Knöpfle, N. Saupper, J. Hulliger, P. Günter, and W. Petter, “Nonlinear-optical, optical, and crystallographic properties of N-(4-nitro-2-pyridinyl)-phenylalaninol,” J. Opt. Soc. Am. B 8, 1483–1490 (1991).

K. Sutter, C. Bosshard, L. Baraldi, and P. Günter, “Nonlinear optical and electro-optic properties of 2(N-prolinol)-5-nitropyridine (PNP) crystals,” AIP Conf. Proc. 103, 127–132 (1989), Sec. 2.1.

P. Kerkoc, M. Zgonik, C. Bosshard, K. Sutter, and P. Günter, “Optical and nonlinear optical properties of 4-(N, N-dimethylamino)-3-acetamidonitrobenzene single crystals,” Appl. Phys. Lett. 54, 2062–2064 (1989).

K. Sutter, C. Bosshard, W. S. Wang, G. Surmely, and P. Günter, “Linear and nonlinear optical properties of 2(N-prolinol)-5-nitropyridine,” Appl. Phys. Lett. 53, 1779–1781 (1988).

Guyer, D. R.

Hall, S. R.

S. R. Hall, P. V. Kolinsky, R. Jones, S. Allen, P. Gordon, B. Bothwell, D. Bloor, P. A. Norman, M. Hursthouse, A. Karaulov, J. Baldwin, M. Goodyear, and D. Bishop, “Polymorphism and nonlinear optical activity in organic crystals,” J. Cryst. Growth 79, 745–751 (1986).

Hierle, R.

M. Sigelle and R. Hierle, “Determination of the electrooptic coefficients of 3-methyl 4-nitropyridine 1-oxide by an inter-ferometric phase modulation technique,” J. Appl. Phys. 52, 4199–4204 (1981).

Hulliger, J.

Hursthouse, M.

S. R. Hall, P. V. Kolinsky, R. Jones, S. Allen, P. Gordon, B. Bothwell, D. Bloor, P. A. Norman, M. Hursthouse, A. Karaulov, J. Baldwin, M. Goodyear, and D. Bishop, “Polymorphism and nonlinear optical activity in organic crystals,” J. Cryst. Growth 79, 745–751 (1986).

Jerphagnon, J.

J. Jerphagnon and S. K. Kurtz, “Maker fringes: a detailed comparison of theory and experiment for isotropic and uniaxial crystals,” J. Appl. Phys. 41, 1667–1681 (1970).

Jones, R.

S. R. Hall, P. V. Kolinsky, R. Jones, S. Allen, P. Gordon, B. Bothwell, D. Bloor, P. A. Norman, M. Hursthouse, A. Karaulov, J. Baldwin, M. Goodyear, and D. Bishop, “Polymorphism and nonlinear optical activity in organic crystals,” J. Cryst. Growth 79, 745–751 (1986).

Josse, D.

Karaulov, A.

S. R. Hall, P. V. Kolinsky, R. Jones, S. Allen, P. Gordon, B. Bothwell, D. Bloor, P. A. Norman, M. Hursthouse, A. Karaulov, J. Baldwin, M. Goodyear, and D. Bishop, “Polymorphism and nonlinear optical activity in organic crystals,” J. Cryst. Growth 79, 745–751 (1986).

Kaz, A.

Kerkoc, P.

P. Kerkoc, M. Zgonik, C. Bosshard, K. Sutter, and P. Günter, “Optical and nonlinear optical properties of 4-(N, N-dimethylamino)-3-acetamidonitrobenzene single crystals,” Appl. Phys. Lett. 54, 2062–2064 (1989).

Knöpfle, G.

C. Serbutoviez, C. Bosshard, G. Knöpfle, P. Wyss, P. Pre⁁tre, P. Günter, K. Schenk, E. Solari, and G. Chapuis, “Hydrazone derivatives, an efficient class of crystalline materials for nonlinear optics,” Chem. Mater. 7, 1198–1206 (1995).

G. Knöpfle, R. Schlesser, R. Ducret, and P. Günter, “Optical and nonlinear optical properties of 4′-dimethylamino-N-methyl-4-stilbazolium tosylate (DAST) crystals,” Nonlin. Opt. 9, 143–149 (1995).

C. Bosshard, G. Knöpfle, P. Pre⁁tre, S. Follonier, C. Serbutoviez, and P. Günter, “Molecular crystals and polymers for nonlinear optics,” Opt. Eng. 34, 1951–1960 (1995).

K. Sutter, G. Knöpfle, N. Saupper, J. Hulliger, P. Günter, and W. Petter, “Nonlinear-optical, optical, and crystallographic properties of N-(4-nitro-2-pyridinyl)-phenylalaninol,” J. Opt. Soc. Am. B 8, 1483–1490 (1991).

Kolinsky, P. V.

S. R. Hall, P. V. Kolinsky, R. Jones, S. Allen, P. Gordon, B. Bothwell, D. Bloor, P. A. Norman, M. Hursthouse, A. Karaulov, J. Baldwin, M. Goodyear, and D. Bishop, “Polymorphism and nonlinear optical activity in organic crystals,” J. Cryst. Growth 79, 745–751 (1986).

Kurtz, S. K.

J. Jerphagnon and S. K. Kurtz, “Maker fringes: a detailed comparison of theory and experiment for isotropic and uniaxial crystals,” J. Appl. Phys. 41, 1667–1681 (1970).

S. K. Kurtz and T. T. Perry, “A powder technique for the evaluation of nonlinear optical materials,” J. Appl. Phys. 39, 3798–3813 (1968).

Laschewsky, A.

C. Bubeck, A. Laschewsky, D. Lupo, D. Neher, P. Ottenbreit, W. Paulus, W. Prass, H. Ringsdorf, and G. Wegner, “Amphiphilic dyes for nonlinear optics: dependence of second harmonic generation on functional group substitution,” Adv. Mater. 3, 54–58 (1991).

D. Lupo, W. Prass, U. Scheunemann, A. Laschewsky, H. Ringsdorf, and I. Ledoux, “Second-harmonic generation in Langmuir–Blodgett monolayers of stilbazium salt and phenylhydrazone dyes,” J. Opt. Soc. Am. B 5, 300–308 (1988).

Ledoux, I.

I. Ledoux, C. Lepers, A. Périgaud, J. Badan, and J. Zyss, “Linear and nonlinear optical properties of N-4nitrophenyl-L-prolinol single crystals,” Opt. Commun. 80, 149–154 (1990).

D. Lupo, W. Prass, U. Scheunemann, A. Laschewsky, H. Ringsdorf, and I. Ledoux, “Second-harmonic generation in Langmuir–Blodgett monolayers of stilbazium salt and phenylhydrazone dyes,” J. Opt. Soc. Am. B 5, 300–308 (1988).

Lepers, C.

I. Ledoux, C. Lepers, A. Périgaud, J. Badan, and J. Zyss, “Linear and nonlinear optical properties of N-4nitrophenyl-L-prolinol single crystals,” Opt. Commun. 80, 149–154 (1990).

Lupo, D.

C. Bubeck, A. Laschewsky, D. Lupo, D. Neher, P. Ottenbreit, W. Paulus, W. Prass, H. Ringsdorf, and G. Wegner, “Amphiphilic dyes for nonlinear optics: dependence of second harmonic generation on functional group substitution,” Adv. Mater. 3, 54–58 (1991).

D. Lupo, W. Prass, U. Scheunemann, A. Laschewsky, H. Ringsdorf, and I. Ledoux, “Second-harmonic generation in Langmuir–Blodgett monolayers of stilbazium salt and phenylhydrazone dyes,” J. Opt. Soc. Am. B 5, 300–308 (1988).

Marder, S. R.

S. R. Marder, J. W. Perry, and C. P. Yakymyshyn, “Organic salts with large second-order optical nonlinearities,” Chem. Mater. 6, 1137–1147 (1994).

J. W. Perry, S. R. Marder, K. J. Perry, E. T. Sleva, C. Yakymyshyn, K. R. Stewart, and E. P. Boden, “Organic salts with large electro-optic coefficients,” in Nonlinear Optical Properties of Organic Materials IV, K. D. Singer, ed., Proc. SPIE 1560, 302–309 (1991).

S. R. Marder, J. W. Perry, and W. P. Schaeffer, “Synthesis of organic salts with large second-order optical nonlinearities,” Science 245, 626–628 (1989).

Marshall, L. R.

Neher, D.

C. Bubeck, A. Laschewsky, D. Lupo, D. Neher, P. Ottenbreit, W. Paulus, W. Prass, H. Ringsdorf, and G. Wegner, “Amphiphilic dyes for nonlinear optics: dependence of second harmonic generation on functional group substitution,” Adv. Mater. 3, 54–58 (1991).

Norman, P. A.

S. R. Hall, P. V. Kolinsky, R. Jones, S. Allen, P. Gordon, B. Bothwell, D. Bloor, P. A. Norman, M. Hursthouse, A. Karaulov, J. Baldwin, M. Goodyear, and D. Bishop, “Polymorphism and nonlinear optical activity in organic crystals,” J. Cryst. Growth 79, 745–751 (1986).

Ottenbreit, P.

C. Bubeck, A. Laschewsky, D. Lupo, D. Neher, P. Ottenbreit, W. Paulus, W. Prass, H. Ringsdorf, and G. Wegner, “Amphiphilic dyes for nonlinear optics: dependence of second harmonic generation on functional group substitution,” Adv. Mater. 3, 54–58 (1991).

Oudar, J. L.

J. Zyss and J. L. Oudar, “Relation between microscopic and macroscopic low-order optical nonlinearities of molecular crystals with one- or two-dimensional units,” Phys. Rev. A 26, 2028–2048 (1982).

J. L. Oudar, “Optical nonlinearities of conjugated molecules. Stilbene derivatives and highly polar aromatics,” J. Chem. Phys. 67, 446–457 (1977).

Pan, F.

F. Pan, C. Bosshard, M. S. Wong, C. Serbutoviez, S. Follonier, P. Günter, and K. Schenk, “Polymorphism, growth and characterization of a new organic nonlinear optical crystal: 4-dimethylaminobenzaldehyde-4-nitrophenylhydrazone (DANPH),” J. Cryst. Growth 165, 273–283 (1996).

Paulus, W.

C. Bubeck, A. Laschewsky, D. Lupo, D. Neher, P. Ottenbreit, W. Paulus, W. Prass, H. Ringsdorf, and G. Wegner, “Amphiphilic dyes for nonlinear optics: dependence of second harmonic generation on functional group substitution,” Adv. Mater. 3, 54–58 (1991).

Périgaud, A.

I. Ledoux, C. Lepers, A. Périgaud, J. Badan, and J. Zyss, “Linear and nonlinear optical properties of N-4nitrophenyl-L-prolinol single crystals,” Opt. Commun. 80, 149–154 (1990).

Perry, J. W.

S. R. Marder, J. W. Perry, and C. P. Yakymyshyn, “Organic salts with large second-order optical nonlinearities,” Chem. Mater. 6, 1137–1147 (1994).

J. W. Perry, S. R. Marder, K. J. Perry, E. T. Sleva, C. Yakymyshyn, K. R. Stewart, and E. P. Boden, “Organic salts with large electro-optic coefficients,” in Nonlinear Optical Properties of Organic Materials IV, K. D. Singer, ed., Proc. SPIE 1560, 302–309 (1991).

S. R. Marder, J. W. Perry, and W. P. Schaeffer, “Synthesis of organic salts with large second-order optical nonlinearities,” Science 245, 626–628 (1989).

Perry, K. J.

J. W. Perry, S. R. Marder, K. J. Perry, E. T. Sleva, C. Yakymyshyn, K. R. Stewart, and E. P. Boden, “Organic salts with large electro-optic coefficients,” in Nonlinear Optical Properties of Organic Materials IV, K. D. Singer, ed., Proc. SPIE 1560, 302–309 (1991).

Perry, T. T.

S. K. Kurtz and T. T. Perry, “A powder technique for the evaluation of nonlinear optical materials,” J. Appl. Phys. 39, 3798–3813 (1968).

Petter, W.

Prass, W.

C. Bubeck, A. Laschewsky, D. Lupo, D. Neher, P. Ottenbreit, W. Paulus, W. Prass, H. Ringsdorf, and G. Wegner, “Amphiphilic dyes for nonlinear optics: dependence of second harmonic generation on functional group substitution,” Adv. Mater. 3, 54–58 (1991).

D. Lupo, W. Prass, U. Scheunemann, A. Laschewsky, H. Ringsdorf, and I. Ledoux, “Second-harmonic generation in Langmuir–Blodgett monolayers of stilbazium salt and phenylhydrazone dyes,” J. Opt. Soc. Am. B 5, 300–308 (1988).

Pre?tre, P.

C. Serbutoviez, C. Bosshard, G. Knöpfle, P. Wyss, P. Pre⁁tre, P. Günter, K. Schenk, E. Solari, and G. Chapuis, “Hydrazone derivatives, an efficient class of crystalline materials for nonlinear optics,” Chem. Mater. 7, 1198–1206 (1995).

C. Bosshard, G. Knöpfle, P. Pre⁁tre, S. Follonier, C. Serbutoviez, and P. Günter, “Molecular crystals and polymers for nonlinear optics,” Opt. Eng. 34, 1951–1960 (1995).

Ringsdorf, H.

C. Bubeck, A. Laschewsky, D. Lupo, D. Neher, P. Ottenbreit, W. Paulus, W. Prass, H. Ringsdorf, and G. Wegner, “Amphiphilic dyes for nonlinear optics: dependence of second harmonic generation on functional group substitution,” Adv. Mater. 3, 54–58 (1991).

D. Lupo, W. Prass, U. Scheunemann, A. Laschewsky, H. Ringsdorf, and I. Ledoux, “Second-harmonic generation in Langmuir–Blodgett monolayers of stilbazium salt and phenylhydrazone dyes,” J. Opt. Soc. Am. B 5, 300–308 (1988).

Roberts, D. A.

D. A. Roberts, “Simplified characterization of uniaxial and biaxial nonlinear optical crystals: a plea for standardization of nomenclature and conventions,” IEEE J. Quantum Electron. 28, 2057–2074 (1992).

Saupper, N.

Schaeffer, W. P.

S. R. Marder, J. W. Perry, and W. P. Schaeffer, “Synthesis of organic salts with large second-order optical nonlinearities,” Science 245, 626–628 (1989).

Schenk, K.

F. Pan, C. Bosshard, M. S. Wong, C. Serbutoviez, S. Follonier, P. Günter, and K. Schenk, “Polymorphism, growth and characterization of a new organic nonlinear optical crystal: 4-dimethylaminobenzaldehyde-4-nitrophenylhydrazone (DANPH),” J. Cryst. Growth 165, 273–283 (1996).

C. Serbutoviez, C. Bosshard, G. Knöpfle, P. Wyss, P. Pre⁁tre, P. Günter, K. Schenk, E. Solari, and G. Chapuis, “Hydrazone derivatives, an efficient class of crystalline materials for nonlinear optics,” Chem. Mater. 7, 1198–1206 (1995).

Scheunemann, U.

Schlesser, R.

G. Knöpfle, R. Schlesser, R. Ducret, and P. Günter, “Optical and nonlinear optical properties of 4′-dimethylamino-N-methyl-4-stilbazolium tosylate (DAST) crystals,” Nonlin. Opt. 9, 143–149 (1995).

Serbutoviez, C.

F. Pan, C. Bosshard, M. S. Wong, C. Serbutoviez, S. Follonier, P. Günter, and K. Schenk, “Polymorphism, growth and characterization of a new organic nonlinear optical crystal: 4-dimethylaminobenzaldehyde-4-nitrophenylhydrazone (DANPH),” J. Cryst. Growth 165, 273–283 (1996).

C. Serbutoviez, C. Bosshard, G. Knöpfle, P. Wyss, P. Pre⁁tre, P. Günter, K. Schenk, E. Solari, and G. Chapuis, “Hydrazone derivatives, an efficient class of crystalline materials for nonlinear optics,” Chem. Mater. 7, 1198–1206 (1995).

C. Bosshard, G. Knöpfle, P. Pre⁁tre, S. Follonier, C. Serbutoviez, and P. Günter, “Molecular crystals and polymers for nonlinear optics,” Opt. Eng. 34, 1951–1960 (1995).

Sheik-Bahae, M.

Shumate, M. S.

Sigelle, M.

M. Sigelle and R. Hierle, “Determination of the electrooptic coefficients of 3-methyl 4-nitropyridine 1-oxide by an inter-ferometric phase modulation technique,” J. Appl. Phys. 52, 4199–4204 (1981).

Sleva, E. T.

J. W. Perry, S. R. Marder, K. J. Perry, E. T. Sleva, C. Yakymyshyn, K. R. Stewart, and E. P. Boden, “Organic salts with large electro-optic coefficients,” in Nonlinear Optical Properties of Organic Materials IV, K. D. Singer, ed., Proc. SPIE 1560, 302–309 (1991).

Solari, E.

C. Serbutoviez, C. Bosshard, G. Knöpfle, P. Wyss, P. Pre⁁tre, P. Günter, K. Schenk, E. Solari, and G. Chapuis, “Hydrazone derivatives, an efficient class of crystalline materials for nonlinear optics,” Chem. Mater. 7, 1198–1206 (1995).

Spence, D. E.

Stegeman, G. I.

Stewart, K. R.

J. W. Perry, S. R. Marder, K. J. Perry, E. T. Sleva, C. Yakymyshyn, K. R. Stewart, and E. P. Boden, “Organic salts with large electro-optic coefficients,” in Nonlinear Optical Properties of Organic Materials IV, K. D. Singer, ed., Proc. SPIE 1560, 302–309 (1991).

Surmely, G.

K. Sutter, C. Bosshard, W. S. Wang, G. Surmely, and P. Günter, “Linear and nonlinear optical properties of 2(N-prolinol)-5-nitropyridine,” Appl. Phys. Lett. 53, 1779–1781 (1988).

Sutter, K.

K. Sutter, G. Knöpfle, N. Saupper, J. Hulliger, P. Günter, and W. Petter, “Nonlinear-optical, optical, and crystallographic properties of N-(4-nitro-2-pyridinyl)-phenylalaninol,” J. Opt. Soc. Am. B 8, 1483–1490 (1991).

K. Sutter, C. Bosshard, L. Baraldi, and P. Günter, “Nonlinear optical and electro-optic properties of 2(N-prolinol)-5-nitropyridine (PNP) crystals,” AIP Conf. Proc. 103, 127–132 (1989), Sec. 2.1.

P. Kerkoc, M. Zgonik, C. Bosshard, K. Sutter, and P. Günter, “Optical and nonlinear optical properties of 4-(N, N-dimethylamino)-3-acetamidonitrobenzene single crystals,” Appl. Phys. Lett. 54, 2062–2064 (1989).

K. Sutter, C. Bosshard, W. S. Wang, G. Surmely, and P. Günter, “Linear and nonlinear optical properties of 2(N-prolinol)-5-nitropyridine,” Appl. Phys. Lett. 53, 1779–1781 (1988).

Tang, C. L.

VanStryland, E.

Vecchiotto, L.

L. Vecchiotto, “Ricerche sulli idrazoni,” Gazz. Chim. Ital. 43, 637–643 (1913).

Vodopyanov, K. L.

Wang, W. S.

K. Sutter, C. Bosshard, W. S. Wang, G. Surmely, and P. Günter, “Linear and nonlinear optical properties of 2(N-prolinol)-5-nitropyridine,” Appl. Phys. Lett. 53, 1779–1781 (1988).

Wegner, G.

C. Bubeck, A. Laschewsky, D. Lupo, D. Neher, P. Ottenbreit, W. Paulus, W. Prass, H. Ringsdorf, and G. Wegner, “Amphiphilic dyes for nonlinear optics: dependence of second harmonic generation on functional group substitution,” Adv. Mater. 3, 54–58 (1991).

Wielandy, S.

Wong, M. S.

F. Pan, C. Bosshard, M. S. Wong, C. Serbutoviez, S. Follonier, P. Günter, and K. Schenk, “Polymorphism, growth and characterization of a new organic nonlinear optical crystal: 4-dimethylaminobenzaldehyde-4-nitrophenylhydrazone (DANPH),” J. Cryst. Growth 165, 273–283 (1996).

Wyncke, B.

F. Brehat and B. Wyncke, “Calculation of double-refraction walk-off angle along the phase-matching directions in non-linear biaxial crystals,” J. Phys. B 22, 1891–1898 (1989).

B. Wyncke and F. Brehat, “Calculation of the effective second-order non-linear coefficients along the phase matching directions in acentric orthorhombic biaxial crystals,” J. Phys. B 22, 363–376 (1989).

Wyss, P.

C. Serbutoviez, C. Bosshard, G. Knöpfle, P. Wyss, P. Pre⁁tre, P. Günter, K. Schenk, E. Solari, and G. Chapuis, “Hydrazone derivatives, an efficient class of crystalline materials for nonlinear optics,” Chem. Mater. 7, 1198–1206 (1995).

Yakymyshyn, C.

J. W. Perry, S. R. Marder, K. J. Perry, E. T. Sleva, C. Yakymyshyn, K. R. Stewart, and E. P. Boden, “Organic salts with large electro-optic coefficients,” in Nonlinear Optical Properties of Organic Materials IV, K. D. Singer, ed., Proc. SPIE 1560, 302–309 (1991).

Yakymyshyn, C. P.

S. R. Marder, J. W. Perry, and C. P. Yakymyshyn, “Organic salts with large second-order optical nonlinearities,” Chem. Mater. 6, 1137–1147 (1994).

Zgonik, M.

P. Kerkoc, M. Zgonik, C. Bosshard, K. Sutter, and P. Günter, “Optical and nonlinear optical properties of 4-(N, N-dimethylamino)-3-acetamidonitrobenzene single crystals,” Appl. Phys. Lett. 54, 2062–2064 (1989).

Zyss, J.

S. X. Dou, D. Josse, and J. Zyss, “Near-infrared pulsed optical parametric oscillation in N-(4-nitrophenyl)L-prolinol at the 1-ns time scale,” J. Opt. Soc. Am. B 10, 1708–1715 (1993).

S. X. Dou, D. Josse, and J. Zyss, “Comparison of collinear and one-beam noncritical noncollinear phase matching in optical parametric amplification,” J. Opt. Soc. Am. B 9, 1312–1319 (1992).

I. Ledoux, C. Lepers, A. Périgaud, J. Badan, and J. Zyss, “Linear and nonlinear optical properties of N-4nitrophenyl-L-prolinol single crystals,” Opt. Commun. 80, 149–154 (1990).

J. Zyss and J. L. Oudar, “Relation between microscopic and macroscopic low-order optical nonlinearities of molecular crystals with one- or two-dimensional units,” Phys. Rev. A 26, 2028–2048 (1982).

Adv. Mater. (1)

C. Bubeck, A. Laschewsky, D. Lupo, D. Neher, P. Ottenbreit, W. Paulus, W. Prass, H. Ringsdorf, and G. Wegner, “Amphiphilic dyes for nonlinear optics: dependence of second harmonic generation on functional group substitution,” Adv. Mater. 3, 54–58 (1991).

AIP Conf. Proc. (1)

K. Sutter, C. Bosshard, L. Baraldi, and P. Günter, “Nonlinear optical and electro-optic properties of 2(N-prolinol)-5-nitropyridine (PNP) crystals,” AIP Conf. Proc. 103, 127–132 (1989), Sec. 2.1.

Appl. Opt. (1)

Appl. Phys. Lett. (2)

P. Kerkoc, M. Zgonik, C. Bosshard, K. Sutter, and P. Günter, “Optical and nonlinear optical properties of 4-(N, N-dimethylamino)-3-acetamidonitrobenzene single crystals,” Appl. Phys. Lett. 54, 2062–2064 (1989).

K. Sutter, C. Bosshard, W. S. Wang, G. Surmely, and P. Günter, “Linear and nonlinear optical properties of 2(N-prolinol)-5-nitropyridine,” Appl. Phys. Lett. 53, 1779–1781 (1988).

Chem. Mater. (2)

S. R. Marder, J. W. Perry, and C. P. Yakymyshyn, “Organic salts with large second-order optical nonlinearities,” Chem. Mater. 6, 1137–1147 (1994).

C. Serbutoviez, C. Bosshard, G. Knöpfle, P. Wyss, P. Pre⁁tre, P. Günter, K. Schenk, E. Solari, and G. Chapuis, “Hydrazone derivatives, an efficient class of crystalline materials for nonlinear optics,” Chem. Mater. 7, 1198–1206 (1995).

Gazz. Chim. Ital. (1)

L. Vecchiotto, “Ricerche sulli idrazoni,” Gazz. Chim. Ital. 43, 637–643 (1913).

IEEE J. Quantum Electron. (1)

D. A. Roberts, “Simplified characterization of uniaxial and biaxial nonlinear optical crystals: a plea for standardization of nomenclature and conventions,” IEEE J. Quantum Electron. 28, 2057–2074 (1992).

J. Appl. Phys. (3)

J. Jerphagnon and S. K. Kurtz, “Maker fringes: a detailed comparison of theory and experiment for isotropic and uniaxial crystals,” J. Appl. Phys. 41, 1667–1681 (1970).

M. Sigelle and R. Hierle, “Determination of the electrooptic coefficients of 3-methyl 4-nitropyridine 1-oxide by an inter-ferometric phase modulation technique,” J. Appl. Phys. 52, 4199–4204 (1981).

S. K. Kurtz and T. T. Perry, “A powder technique for the evaluation of nonlinear optical materials,” J. Appl. Phys. 39, 3798–3813 (1968).

J. Chem. Phys. (1)

J. L. Oudar, “Optical nonlinearities of conjugated molecules. Stilbene derivatives and highly polar aromatics,” J. Chem. Phys. 67, 446–457 (1977).

J. Cryst. Growth (2)

S. R. Hall, P. V. Kolinsky, R. Jones, S. Allen, P. Gordon, B. Bothwell, D. Bloor, P. A. Norman, M. Hursthouse, A. Karaulov, J. Baldwin, M. Goodyear, and D. Bishop, “Polymorphism and nonlinear optical activity in organic crystals,” J. Cryst. Growth 79, 745–751 (1986).

F. Pan, C. Bosshard, M. S. Wong, C. Serbutoviez, S. Follonier, P. Günter, and K. Schenk, “Polymorphism, growth and characterization of a new organic nonlinear optical crystal: 4-dimethylaminobenzaldehyde-4-nitrophenylhydrazone (DANPH),” J. Cryst. Growth 165, 273–283 (1996).

J. Opt. Soc. Am. B (7)

J. Phys. B (2)

B. Wyncke and F. Brehat, “Calculation of the effective second-order non-linear coefficients along the phase matching directions in acentric orthorhombic biaxial crystals,” J. Phys. B 22, 363–376 (1989).

F. Brehat and B. Wyncke, “Calculation of double-refraction walk-off angle along the phase-matching directions in non-linear biaxial crystals,” J. Phys. B 22, 1891–1898 (1989).

Nonlin. Opt. (1)

G. Knöpfle, R. Schlesser, R. Ducret, and P. Günter, “Optical and nonlinear optical properties of 4′-dimethylamino-N-methyl-4-stilbazolium tosylate (DAST) crystals,” Nonlin. Opt. 9, 143–149 (1995).

Opt. Commun. (1)

I. Ledoux, C. Lepers, A. Périgaud, J. Badan, and J. Zyss, “Linear and nonlinear optical properties of N-4nitrophenyl-L-prolinol single crystals,” Opt. Commun. 80, 149–154 (1990).

Opt. Eng. (1)

C. Bosshard, G. Knöpfle, P. Pre⁁tre, S. Follonier, C. Serbutoviez, and P. Günter, “Molecular crystals and polymers for nonlinear optics,” Opt. Eng. 34, 1951–1960 (1995).

Opt. Lett. (2)

Phys. Rev. A (1)

J. Zyss and J. L. Oudar, “Relation between microscopic and macroscopic low-order optical nonlinearities of molecular crystals with one- or two-dimensional units,” Phys. Rev. A 26, 2028–2048 (1982).

Proc. SPIE (1)

J. W. Perry, S. R. Marder, K. J. Perry, E. T. Sleva, C. Yakymyshyn, K. R. Stewart, and E. P. Boden, “Organic salts with large electro-optic coefficients,” in Nonlinear Optical Properties of Organic Materials IV, K. D. Singer, ed., Proc. SPIE 1560, 302–309 (1991).

Science (1)

S. R. Marder, J. W. Perry, and W. P. Schaeffer, “Synthesis of organic salts with large second-order optical nonlinearities,” Science 245, 626–628 (1989).

Other (8)

C. P. Yakymyshyn, K. R. Stewart, E. P. Boden, S. R. Marder, J. W. Perry, and W. P. Schaefer, “Second-order non-linear optical properties of 4-N-methylstilbazolium tosylate salts,” Royal Society of Chemistry Special Publication 91, R. A. Hann and D. Bloor, eds. (Royal Society of Chemistry, London, 1991), pp. 108–114.

J. Zyss, Molecular Nonlinear Optics (Academic, San Diego, Calif., 1994), Chap. 4, pp. 148–150.

W. Hickel, J. Bauer, D. Lupo, B. Menzel, U. Falk, and U. Scheunemann, “Second-harmonic generation in alternating Langmuir–Blodgett multilayers,” presented at the Organic Materials for Nonlinear Optics III Meeting, August 19–21, 1993, Oxford.

J. F. Nicoud and R. J. Twieg, “Design and synthesis of organic molecular compounds for efficient second-harmonic generation,” Nonlin. Opt. Properties Org. Mol. Cryst. 1, 227–296 (1987).

J. N. Brown, T. M. Kutchan, and P. E. Rist, “p-Dimethylamino-benzaldehyde-p-nitronphenyl-hydrazone benzene,” Cryst. Struct. Commun. 9, 17–22 (1980).

M. Born and E. Wolf, Principles of Optics, 6th ed. (Pergamon, Oxford, 1980), pp. 96–97.

J.-C. Baumert, J. Hoffnagle, and P. Günter, “Nonlinear optical effects in KNbO3 crystals at AlxGa1−xAs, dye, ruby and Nd:YAG laser wavelengths,” presented at the 1984 European Conference on Optics, Optical Systems, and Applications, October 9–12, 1984, Amsterdam.

C. Bosshard, K. Sutter, P. Pre⁁tre, J. Hulliger, M. Flörsheimer, P. Kaatz, and P. Günter, “Organic nonlinear optical materials,” in Advances in Nonlinear Optics (Gordon & Breach, Basel, Switzerland, 1995), Vol. 1, Chap. 4, pp. 106–114.

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