Abstract

The quadratic nonlinear optical efficiency of the 2-amino-5-nitropyridinium dihydrogen chloride crystal is studied. The quadratic coefficients are determined by second-harmonic generation as d11=9 pm/V and d12=8 pm/V. The effective coefficients are obtained as deff=5.1 pm/V for type I and deff=9.7 pm/V for type II. Following the gas-oriented model, the dimensions of the hyperpolarizability tensor bIJK of the 2-amino-5-nitropyridinium are examined. Considering the arrangement of the organic and inorganic entities in the unit cell, the failure of the two-dimensional model can be due to the local electric field induced by the Cl anions.

© 2002 Optical Society of America

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  21. N. Horiuchi, F. Lefaucheux, A. Ibanez, D. Josse, and J. Zyss, “An organic-inorganic crystal for blue SHG: crystal growth and quadratic optical effect on 2-amino-5-nitropyrinium chloride,” J. Opt. Mater. 12, 351–356 (1999).
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  26. F. Béhat 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).
  27. J. Zyss, D. S. Chemla, and J. F. Nicoud, “Demonstration of efficient nonlinear optical crystals with vanishing molecular dipole moment: second-harmonic generation in 3-methyl-4-nitropyridine-1-oxide,” J. Chem. Phys. 74, 4800–4811 (1981).
  28. 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).
  29. P. Günter, C. Bosshard, K. Sutter, H. Arend, G. Chapuis, R. J. Twieg, and D. Dobrowolski, “2-cyclooctylamino-5-nitropyridine, a new nonlinear optical crystal with orthorhombic symmetry,” Appl. Phys. Lett. 50, 486–488 (1987).
  30. P. Kerkoc, M. Zgonik, K. Sutter, C. Bosshard, and P. Günter, “4-(N, N-dimethylamino)-3-acetamidonitrobenzene single crystals for nonlinear optical applications,” J. Opt. Soc. Am. B 7, 313–319 (1990).
  31. J. L. Oudar and R. Hierle, “An efficient organic crystal for nonlinear optics: methyl-(2, 4-dinitrophenyl)-aminopropanoate,” J. Appl. Phys. 48, 2699–2704 (1977).
  32. P. D. Southgate and D. S. Hall, “Anomalously high nonlinear optical effects in m-nitroaniline,” Appl. Phys. Lett. 18, 456–458 (1971).
  33. R. Morita and P. V. Vidaković, “Angle and temperature tuning of phase-matched second-harmonic generation in N-(4-nitrophenyl)-N-methylaminoacetonitrile,” Appl. Phys. Lett. 61, 2854–2856 (1992).
  34. J. D. Bierlein, L. K. Cheng, Y. Wand, and W. Tam, “Linear and nonlinear optical properties of 3-methyl-4-methoxy-4-nitrostilbene single crystals,” Appl. Phys. Lett. 56, 423–425 (1990).

1999 (2)

J. P. Fève, B. Boulanger, I. Rousseau, G. Marnier, J. Zaccaro, and A. Ibanez, “Second-harmonic generation properties of 2-amino-5-nitropyridium-dihydrogenoarsenate and dihydrogenophosphate organic–inorganic crystals,” IEEE J. Quantum Electron. 35, 66–71 (1999).

N. Horiuchi, F. Lefaucheux, A. Ibanez, D. Josse, and J. Zyss, “An organic-inorganic crystal for blue SHG: crystal growth and quadratic optical effect on 2-amino-5-nitropyrinium chloride,” J. Opt. Mater. 12, 351–356 (1999).

1998 (1)

J. Zyss, S. Brasselet, V. R. Thalladi, and G. R. Desiraju, “Octupolar versus dipolar crystalline structures for nonlinear optics: a dual crystal and propagative engineering approach,” J. Chem. Phys. 109, 658–669 (1998).

1997 (2)

J. F. Nicoud, R. Masse, C. Bourgogne, and C. Evans, “Perfect layered arrangement of ion-paired chromophores in a crystalline non-linear optical organic salt: 2-amino-3-nitropyridinium chloride,” J. Mater. Chem. 7, 35–39 (1997).

A. Ibanez, J. P. Lévy, C. Mouget, and E. Prieur, “Crystal growth of a promising nonlinear optical material: 2-amino-5-nitropyridinium-chloride,” J. Solid State Chem. 129, 22–29 (1997).

1995 (1)

N. Horiuchi, F. Lefaucheux, M. C. Robert, D. Josse, S. Khodja, and J. Zyss, “Gel growth of 2-amino-5-nitropyridinium dihydrogen phosphate organomineral crystals: x-ray and nonlinear optics characterization,” J. Cryst. Growth 147, 361–368 (1995).

1993 (3)

J. Pécaut, J. P. Lévy, and R. Masse, “Structural evidence in 2-amino-5-nitropyridinium halides (Cl, Br) of herringbone motifs favourable to efficient quadratic non-linear optical properties,” J. Mater. Chem. 3, 999–1003 (1993).

R. Masse, M. Bagieu-Beucher, J. Pécaut, J. P. Lévy, and J. Zyss, “Design of organic–inorganic polar crystals for quadratic nonlinear optics,” Nonlinear Opt. 5, 413–423 (1993).

J. Zyss, R. Masse, M. Bagieu-Beucher, and J. P. Lévy, “Quasi-perfect polar alignment of nonlinear chromophores in a crystalline H-bonded guest–host structure: 2-amino-5-nitropyridinium-L-monohydrogentartrate,” Adv. Mater. 5, 120–124 (1993).

1992 (3)

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).

R. Morita and P. V. Vidaković, “Angle and temperature tuning of phase-matched second-harmonic generation in N-(4-nitrophenyl)-N-methylaminoacetonitrile,” Appl. Phys. Lett. 61, 2854–2856 (1992).

Z. Kotler, R. Hierle, D. Josse, J. Zyss, and R. Masse, “Quadratic nonlinear-optical properties of a new transparent and highly efficient organic-inorganic crystal: 2-amino-5-nitropyridium-dihydrogen phosphate (2A5NPDP),” J. Opt. Soc. Am. B 9, 534–547 (1992).

1991 (2)

R. Masse and J. Zyss, “A new approach in the design of polar crystals for quadratic nonlinear optics exemplified by the synthesis of 2-amino-5-nitropyridium-dihydrogen monophosphate (2A5NPDP),” Mol. Eng. 1, 141–152 (1991).

J. Zyss, “Octupolar organic systems in quadratic nonlinear optics: molecules and materials,” Nonlinear Opt. 1, 3–18 (1991).

1990 (3)

J. D. Bierlein, L. K. Cheng, Y. Wand, and W. Tam, “Linear and nonlinear optical properties of 3-methyl-4-methoxy-4-nitrostilbene single crystals,” Appl. Phys. Lett. 56, 423–425 (1990).

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

P. Kerkoc, M. Zgonik, K. Sutter, C. Bosshard, and P. Günter, “4-(N, N-dimethylamino)-3-acetamidonitrobenzene single crystals for nonlinear optical applications,” J. Opt. Soc. Am. B 7, 313–319 (1990).

1989 (1)

F. Béhat 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 (1)

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).

1987 (3)

1984 (1)

J. Zyss, J. F. Nicoud, and M. Coquillay, “Chirality and hydrogen bonding in molecular crystals for phase-matched second-harmonic generation: N-(4-nitrophenyl)-(L)-prolinol (NPP),” J. Chem. Phys. 81, 4160–4167 (1984).

1982 (2)

J. L. Oudar and J. Zyss, “Structural dependence of nonlinear-optical properties of methyl-(2, 4-dinitrophenyl)-aminopropanoate crystals,” Phys. Rev. A 26, 2016–2027 (1982).

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

1981 (1)

J. Zyss, D. S. Chemla, and J. F. Nicoud, “Demonstration of efficient nonlinear optical crystals with vanishing molecular dipole moment: second-harmonic generation in 3-methyl-4-nitropyridine-1-oxide,” J. Chem. Phys. 74, 4800–4811 (1981).

1979 (1)

J. Zyss, “Hyperpolarizabilities of substituted conjugated molecules. II. Substituent effects and respective σ–π contributions,” J. Chem. Phys. 70, 3341–3349 (1979).

1977 (2)

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

J. L. Oudar and R. Hierle, “An efficient organic crystal for nonlinear optics: methyl-(2, 4-dinitrophenyl)-aminopropanoate,” J. Appl. Phys. 48, 2699–2704 (1977).

1971 (1)

P. D. Southgate and D. S. Hall, “Anomalously high nonlinear optical effects in m-nitroaniline,” Appl. Phys. Lett. 18, 456–458 (1971).

Antonetti, A.

Arend, H.

P. Günter, C. Bosshard, K. Sutter, H. Arend, G. Chapuis, R. J. Twieg, and D. Dobrowolski, “2-cyclooctylamino-5-nitropyridine, a new nonlinear optical crystal with orthorhombic symmetry,” Appl. Phys. Lett. 50, 486–488 (1987).

Badan, J.

Bagieu-Beucher, M.

R. Masse, M. Bagieu-Beucher, J. Pécaut, J. P. Lévy, and J. Zyss, “Design of organic–inorganic polar crystals for quadratic nonlinear optics,” Nonlinear Opt. 5, 413–423 (1993).

J. Zyss, R. Masse, M. Bagieu-Beucher, and J. P. Lévy, “Quasi-perfect polar alignment of nonlinear chromophores in a crystalline H-bonded guest–host structure: 2-amino-5-nitropyridinium-L-monohydrogentartrate,” Adv. Mater. 5, 120–124 (1993).

Béhat, F.

F. Béhat 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).

Bierlein, J. D.

J. D. Bierlein, L. K. Cheng, Y. Wand, and W. Tam, “Linear and nonlinear optical properties of 3-methyl-4-methoxy-4-nitrostilbene single crystals,” Appl. Phys. Lett. 56, 423–425 (1990).

Bosshard, C.

P. Kerkoc, M. Zgonik, K. Sutter, C. Bosshard, and P. Günter, “4-(N, N-dimethylamino)-3-acetamidonitrobenzene single crystals for nonlinear optical applications,” J. Opt. Soc. Am. B 7, 313–319 (1990).

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).

P. Günter, C. Bosshard, K. Sutter, H. Arend, G. Chapuis, R. J. Twieg, and D. Dobrowolski, “2-cyclooctylamino-5-nitropyridine, a new nonlinear optical crystal with orthorhombic symmetry,” Appl. Phys. Lett. 50, 486–488 (1987).

Boulanger, B.

J. P. Fève, B. Boulanger, I. Rousseau, G. Marnier, J. Zaccaro, and A. Ibanez, “Second-harmonic generation properties of 2-amino-5-nitropyridium-dihydrogenoarsenate and dihydrogenophosphate organic–inorganic crystals,” IEEE J. Quantum Electron. 35, 66–71 (1999).

Bourgogne, C.

J. F. Nicoud, R. Masse, C. Bourgogne, and C. Evans, “Perfect layered arrangement of ion-paired chromophores in a crystalline non-linear optical organic salt: 2-amino-3-nitropyridinium chloride,” J. Mater. Chem. 7, 35–39 (1997).

Brasselet, S.

J. Zyss, S. Brasselet, V. R. Thalladi, and G. R. Desiraju, “Octupolar versus dipolar crystalline structures for nonlinear optics: a dual crystal and propagative engineering approach,” J. Chem. Phys. 109, 658–669 (1998).

Byer, R. L.

Chapuis, G.

P. Günter, C. Bosshard, K. Sutter, H. Arend, G. Chapuis, R. J. Twieg, and D. Dobrowolski, “2-cyclooctylamino-5-nitropyridine, a new nonlinear optical crystal with orthorhombic symmetry,” Appl. Phys. Lett. 50, 486–488 (1987).

Chemla, D. S.

J. Zyss, D. S. Chemla, and J. F. Nicoud, “Demonstration of efficient nonlinear optical crystals with vanishing molecular dipole moment: second-harmonic generation in 3-methyl-4-nitropyridine-1-oxide,” J. Chem. Phys. 74, 4800–4811 (1981).

Cheng, L. K.

J. D. Bierlein, L. K. Cheng, Y. Wand, and W. Tam, “Linear and nonlinear optical properties of 3-methyl-4-methoxy-4-nitrostilbene single crystals,” Appl. Phys. Lett. 56, 423–425 (1990).

Coquillay, M.

J. Zyss, J. F. Nicoud, and M. Coquillay, “Chirality and hydrogen bonding in molecular crystals for phase-matched second-harmonic generation: N-(4-nitrophenyl)-(L)-prolinol (NPP),” J. Chem. Phys. 81, 4160–4167 (1984).

Desiraju, G. R.

J. Zyss, S. Brasselet, V. R. Thalladi, and G. R. Desiraju, “Octupolar versus dipolar crystalline structures for nonlinear optics: a dual crystal and propagative engineering approach,” J. Chem. Phys. 109, 658–669 (1998).

Dobrowolski, D.

P. Günter, C. Bosshard, K. Sutter, H. Arend, G. Chapuis, R. J. Twieg, and D. Dobrowolski, “2-cyclooctylamino-5-nitropyridine, a new nonlinear optical crystal with orthorhombic symmetry,” Appl. Phys. Lett. 50, 486–488 (1987).

Eckardt, R. C.

Etchepare, J.

Evans, C.

J. F. Nicoud, R. Masse, C. Bourgogne, and C. Evans, “Perfect layered arrangement of ion-paired chromophores in a crystalline non-linear optical organic salt: 2-amino-3-nitropyridinium chloride,” J. Mater. Chem. 7, 35–39 (1997).

Fan, T. Y.

Fan, Y. X.

Feigelson, R. S.

Fève, J. P.

J. P. Fève, B. Boulanger, I. Rousseau, G. Marnier, J. Zaccaro, and A. Ibanez, “Second-harmonic generation properties of 2-amino-5-nitropyridium-dihydrogenoarsenate and dihydrogenophosphate organic–inorganic crystals,” IEEE J. Quantum Electron. 35, 66–71 (1999).

Grillon, G.

Günter, P.

P. Kerkoc, M. Zgonik, K. Sutter, C. Bosshard, and P. Günter, “4-(N, N-dimethylamino)-3-acetamidonitrobenzene single crystals for nonlinear optical applications,” J. Opt. Soc. Am. B 7, 313–319 (1990).

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).

P. Günter, C. Bosshard, K. Sutter, H. Arend, G. Chapuis, R. J. Twieg, and D. Dobrowolski, “2-cyclooctylamino-5-nitropyridine, a new nonlinear optical crystal with orthorhombic symmetry,” Appl. Phys. Lett. 50, 486–488 (1987).

Hall, D. S.

P. D. Southgate and D. S. Hall, “Anomalously high nonlinear optical effects in m-nitroaniline,” Appl. Phys. Lett. 18, 456–458 (1971).

Hierle, R.

Horiuchi, N.

N. Horiuchi, F. Lefaucheux, A. Ibanez, D. Josse, and J. Zyss, “An organic-inorganic crystal for blue SHG: crystal growth and quadratic optical effect on 2-amino-5-nitropyrinium chloride,” J. Opt. Mater. 12, 351–356 (1999).

N. Horiuchi, F. Lefaucheux, M. C. Robert, D. Josse, S. Khodja, and J. Zyss, “Gel growth of 2-amino-5-nitropyridinium dihydrogen phosphate organomineral crystals: x-ray and nonlinear optics characterization,” J. Cryst. Growth 147, 361–368 (1995).

Hu, B. Q.

Huang, C. E.

Hulin, D.

Ibanez, A.

J. P. Fève, B. Boulanger, I. Rousseau, G. Marnier, J. Zaccaro, and A. Ibanez, “Second-harmonic generation properties of 2-amino-5-nitropyridium-dihydrogenoarsenate and dihydrogenophosphate organic–inorganic crystals,” IEEE J. Quantum Electron. 35, 66–71 (1999).

N. Horiuchi, F. Lefaucheux, A. Ibanez, D. Josse, and J. Zyss, “An organic-inorganic crystal for blue SHG: crystal growth and quadratic optical effect on 2-amino-5-nitropyrinium chloride,” J. Opt. Mater. 12, 351–356 (1999).

A. Ibanez, J. P. Lévy, C. Mouget, and E. Prieur, “Crystal growth of a promising nonlinear optical material: 2-amino-5-nitropyridinium-chloride,” J. Solid State Chem. 129, 22–29 (1997).

Josse, D.

N. Horiuchi, F. Lefaucheux, A. Ibanez, D. Josse, and J. Zyss, “An organic-inorganic crystal for blue SHG: crystal growth and quadratic optical effect on 2-amino-5-nitropyrinium chloride,” J. Opt. Mater. 12, 351–356 (1999).

N. Horiuchi, F. Lefaucheux, M. C. Robert, D. Josse, S. Khodja, and J. Zyss, “Gel growth of 2-amino-5-nitropyridinium dihydrogen phosphate organomineral crystals: x-ray and nonlinear optics characterization,” J. Cryst. Growth 147, 361–368 (1995).

Z. Kotler, R. Hierle, D. Josse, J. Zyss, and R. Masse, “Quadratic nonlinear-optical properties of a new transparent and highly efficient organic-inorganic crystal: 2-amino-5-nitropyridium-dihydrogen phosphate (2A5NPDP),” J. Opt. Soc. Am. B 9, 534–547 (1992).

Kerkoc, P.

Khodja, S.

N. Horiuchi, F. Lefaucheux, M. C. Robert, D. Josse, S. Khodja, and J. Zyss, “Gel growth of 2-amino-5-nitropyridinium dihydrogen phosphate organomineral crystals: x-ray and nonlinear optics characterization,” J. Cryst. Growth 147, 361–368 (1995).

Kotler, Z.

Ledoux, I.

Lefaucheux, F.

N. Horiuchi, F. Lefaucheux, A. Ibanez, D. Josse, and J. Zyss, “An organic-inorganic crystal for blue SHG: crystal growth and quadratic optical effect on 2-amino-5-nitropyrinium chloride,” J. Opt. Mater. 12, 351–356 (1999).

N. Horiuchi, F. Lefaucheux, M. C. Robert, D. Josse, S. Khodja, and J. Zyss, “Gel growth of 2-amino-5-nitropyridinium dihydrogen phosphate organomineral crystals: x-ray and nonlinear optics characterization,” J. Cryst. Growth 147, 361–368 (1995).

Lepers, C.

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

Lévy, J. P.

A. Ibanez, J. P. Lévy, C. Mouget, and E. Prieur, “Crystal growth of a promising nonlinear optical material: 2-amino-5-nitropyridinium-chloride,” J. Solid State Chem. 129, 22–29 (1997).

R. Masse, M. Bagieu-Beucher, J. Pécaut, J. P. Lévy, and J. Zyss, “Design of organic–inorganic polar crystals for quadratic nonlinear optics,” Nonlinear Opt. 5, 413–423 (1993).

J. Zyss, R. Masse, M. Bagieu-Beucher, and J. P. Lévy, “Quasi-perfect polar alignment of nonlinear chromophores in a crystalline H-bonded guest–host structure: 2-amino-5-nitropyridinium-L-monohydrogentartrate,” Adv. Mater. 5, 120–124 (1993).

J. Pécaut, J. P. Lévy, and R. Masse, “Structural evidence in 2-amino-5-nitropyridinium halides (Cl, Br) of herringbone motifs favourable to efficient quadratic non-linear optical properties,” J. Mater. Chem. 3, 999–1003 (1993).

Marnier, G.

J. P. Fève, B. Boulanger, I. Rousseau, G. Marnier, J. Zaccaro, and A. Ibanez, “Second-harmonic generation properties of 2-amino-5-nitropyridium-dihydrogenoarsenate and dihydrogenophosphate organic–inorganic crystals,” IEEE J. Quantum Electron. 35, 66–71 (1999).

Masse, R.

J. F. Nicoud, R. Masse, C. Bourgogne, and C. Evans, “Perfect layered arrangement of ion-paired chromophores in a crystalline non-linear optical organic salt: 2-amino-3-nitropyridinium chloride,” J. Mater. Chem. 7, 35–39 (1997).

R. Masse, M. Bagieu-Beucher, J. Pécaut, J. P. Lévy, and J. Zyss, “Design of organic–inorganic polar crystals for quadratic nonlinear optics,” Nonlinear Opt. 5, 413–423 (1993).

J. Pécaut, J. P. Lévy, and R. Masse, “Structural evidence in 2-amino-5-nitropyridinium halides (Cl, Br) of herringbone motifs favourable to efficient quadratic non-linear optical properties,” J. Mater. Chem. 3, 999–1003 (1993).

J. Zyss, R. Masse, M. Bagieu-Beucher, and J. P. Lévy, “Quasi-perfect polar alignment of nonlinear chromophores in a crystalline H-bonded guest–host structure: 2-amino-5-nitropyridinium-L-monohydrogentartrate,” Adv. Mater. 5, 120–124 (1993).

Z. Kotler, R. Hierle, D. Josse, J. Zyss, and R. Masse, “Quadratic nonlinear-optical properties of a new transparent and highly efficient organic-inorganic crystal: 2-amino-5-nitropyridium-dihydrogen phosphate (2A5NPDP),” J. Opt. Soc. Am. B 9, 534–547 (1992).

R. Masse and J. Zyss, “A new approach in the design of polar crystals for quadratic nonlinear optics exemplified by the synthesis of 2-amino-5-nitropyridium-dihydrogen monophosphate (2A5NPDP),” Mol. Eng. 1, 141–152 (1991).

Migus, A.

Morita, R.

R. Morita and P. V. Vidaković, “Angle and temperature tuning of phase-matched second-harmonic generation in N-(4-nitrophenyl)-N-methylaminoacetonitrile,” Appl. Phys. Lett. 61, 2854–2856 (1992).

Mouget, C.

A. Ibanez, J. P. Lévy, C. Mouget, and E. Prieur, “Crystal growth of a promising nonlinear optical material: 2-amino-5-nitropyridinium-chloride,” J. Solid State Chem. 129, 22–29 (1997).

Nicoud, J. F.

J. F. Nicoud, R. Masse, C. Bourgogne, and C. Evans, “Perfect layered arrangement of ion-paired chromophores in a crystalline non-linear optical organic salt: 2-amino-3-nitropyridinium chloride,” J. Mater. Chem. 7, 35–39 (1997).

J. Zyss, J. F. Nicoud, and M. Coquillay, “Chirality and hydrogen bonding in molecular crystals for phase-matched second-harmonic generation: N-(4-nitrophenyl)-(L)-prolinol (NPP),” J. Chem. Phys. 81, 4160–4167 (1984).

J. Zyss, D. S. Chemla, and J. F. Nicoud, “Demonstration of efficient nonlinear optical crystals with vanishing molecular dipole moment: second-harmonic generation in 3-methyl-4-nitropyridine-1-oxide,” J. Chem. Phys. 74, 4800–4811 (1981).

Oudar, J. L.

J. L. Oudar and J. Zyss, “Structural dependence of nonlinear-optical properties of methyl-(2, 4-dinitrophenyl)-aminopropanoate crystals,” Phys. Rev. A 26, 2016–2027 (1982).

J. Zyss and J. L. Oudar, “Relations between microscopic and macroscopic lowest-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 aromatic compounds,” J. Chem. Phys. 67, 446–457 (1977).

J. L. Oudar and R. Hierle, “An efficient organic crystal for nonlinear optics: methyl-(2, 4-dinitrophenyl)-aminopropanoate,” J. Appl. Phys. 48, 2699–2704 (1977).

Pécaut, J.

R. Masse, M. Bagieu-Beucher, J. Pécaut, J. P. Lévy, and J. Zyss, “Design of organic–inorganic polar crystals for quadratic nonlinear optics,” Nonlinear Opt. 5, 413–423 (1993).

J. Pécaut, J. P. Lévy, and R. Masse, “Structural evidence in 2-amino-5-nitropyridinium halides (Cl, Br) of herringbone motifs favourable to efficient quadratic non-linear optical properties,” J. Mater. Chem. 3, 999–1003 (1993).

Périgaud, A.

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

Prieur, E.

A. Ibanez, J. P. Lévy, C. Mouget, and E. Prieur, “Crystal growth of a promising nonlinear optical material: 2-amino-5-nitropyridinium-chloride,” J. Solid State Chem. 129, 22–29 (1997).

Robert, M. C.

N. Horiuchi, F. Lefaucheux, M. C. Robert, D. Josse, S. Khodja, and J. Zyss, “Gel growth of 2-amino-5-nitropyridinium dihydrogen phosphate organomineral crystals: x-ray and nonlinear optics characterization,” J. Cryst. Growth 147, 361–368 (1995).

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).

Rousseau, I.

J. P. Fève, B. Boulanger, I. Rousseau, G. Marnier, J. Zaccaro, and A. Ibanez, “Second-harmonic generation properties of 2-amino-5-nitropyridium-dihydrogenoarsenate and dihydrogenophosphate organic–inorganic crystals,” IEEE J. Quantum Electron. 35, 66–71 (1999).

Southgate, P. D.

P. D. Southgate and D. S. Hall, “Anomalously high nonlinear optical effects in m-nitroaniline,” Appl. Phys. Lett. 18, 456–458 (1971).

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.

P. Kerkoc, M. Zgonik, K. Sutter, C. Bosshard, and P. Günter, “4-(N, N-dimethylamino)-3-acetamidonitrobenzene single crystals for nonlinear optical applications,” J. Opt. Soc. Am. B 7, 313–319 (1990).

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).

P. Günter, C. Bosshard, K. Sutter, H. Arend, G. Chapuis, R. J. Twieg, and D. Dobrowolski, “2-cyclooctylamino-5-nitropyridine, a new nonlinear optical crystal with orthorhombic symmetry,” Appl. Phys. Lett. 50, 486–488 (1987).

Tam, W.

J. D. Bierlein, L. K. Cheng, Y. Wand, and W. Tam, “Linear and nonlinear optical properties of 3-methyl-4-methoxy-4-nitrostilbene single crystals,” Appl. Phys. Lett. 56, 423–425 (1990).

Thalladi, V. R.

J. Zyss, S. Brasselet, V. R. Thalladi, and G. R. Desiraju, “Octupolar versus dipolar crystalline structures for nonlinear optics: a dual crystal and propagative engineering approach,” J. Chem. Phys. 109, 658–669 (1998).

Twieg, R. J.

P. Günter, C. Bosshard, K. Sutter, H. Arend, G. Chapuis, R. J. Twieg, and D. Dobrowolski, “2-cyclooctylamino-5-nitropyridine, a new nonlinear optical crystal with orthorhombic symmetry,” Appl. Phys. Lett. 50, 486–488 (1987).

Vidakovic, P. V.

R. Morita and P. V. Vidaković, “Angle and temperature tuning of phase-matched second-harmonic generation in N-(4-nitrophenyl)-N-methylaminoacetonitrile,” Appl. Phys. Lett. 61, 2854–2856 (1992).

Wand, Y.

J. D. Bierlein, L. K. Cheng, Y. Wand, and W. Tam, “Linear and nonlinear optical properties of 3-methyl-4-methoxy-4-nitrostilbene single crystals,” Appl. Phys. Lett. 56, 423–425 (1990).

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).

Wyncke, B.

F. Béhat 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).

Zaccaro, J.

J. P. Fève, B. Boulanger, I. Rousseau, G. Marnier, J. Zaccaro, and A. Ibanez, “Second-harmonic generation properties of 2-amino-5-nitropyridium-dihydrogenoarsenate and dihydrogenophosphate organic–inorganic crystals,” IEEE J. Quantum Electron. 35, 66–71 (1999).

Zgonik, M.

Zyss, J.

N. Horiuchi, F. Lefaucheux, A. Ibanez, D. Josse, and J. Zyss, “An organic-inorganic crystal for blue SHG: crystal growth and quadratic optical effect on 2-amino-5-nitropyrinium chloride,” J. Opt. Mater. 12, 351–356 (1999).

J. Zyss, S. Brasselet, V. R. Thalladi, and G. R. Desiraju, “Octupolar versus dipolar crystalline structures for nonlinear optics: a dual crystal and propagative engineering approach,” J. Chem. Phys. 109, 658–669 (1998).

N. Horiuchi, F. Lefaucheux, M. C. Robert, D. Josse, S. Khodja, and J. Zyss, “Gel growth of 2-amino-5-nitropyridinium dihydrogen phosphate organomineral crystals: x-ray and nonlinear optics characterization,” J. Cryst. Growth 147, 361–368 (1995).

R. Masse, M. Bagieu-Beucher, J. Pécaut, J. P. Lévy, and J. Zyss, “Design of organic–inorganic polar crystals for quadratic nonlinear optics,” Nonlinear Opt. 5, 413–423 (1993).

J. Zyss, R. Masse, M. Bagieu-Beucher, and J. P. Lévy, “Quasi-perfect polar alignment of nonlinear chromophores in a crystalline H-bonded guest–host structure: 2-amino-5-nitropyridinium-L-monohydrogentartrate,” Adv. Mater. 5, 120–124 (1993).

Z. Kotler, R. Hierle, D. Josse, J. Zyss, and R. Masse, “Quadratic nonlinear-optical properties of a new transparent and highly efficient organic-inorganic crystal: 2-amino-5-nitropyridium-dihydrogen phosphate (2A5NPDP),” J. Opt. Soc. Am. B 9, 534–547 (1992).

R. Masse and J. Zyss, “A new approach in the design of polar crystals for quadratic nonlinear optics exemplified by the synthesis of 2-amino-5-nitropyridium-dihydrogen monophosphate (2A5NPDP),” Mol. Eng. 1, 141–152 (1991).

J. Zyss, “Octupolar organic systems in quadratic nonlinear optics: molecules and materials,” Nonlinear Opt. 1, 3–18 (1991).

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

I. Ledoux, J. Badan, J. Zyss, A. Migus, D. Hulin, J. Etchepare, G. Grillon, and A. Antonetti, “Generation of high-peak power tunable infrared femtosecond pulses in an organic crystal: application to time resolution of weak infrared signals,” J. Opt. Soc. Am. B 4, 987–997 (1987).

J. Zyss, J. F. Nicoud, and M. Coquillay, “Chirality and hydrogen bonding in molecular crystals for phase-matched second-harmonic generation: N-(4-nitrophenyl)-(L)-prolinol (NPP),” J. Chem. Phys. 81, 4160–4167 (1984).

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

J. L. Oudar and J. Zyss, “Structural dependence of nonlinear-optical properties of methyl-(2, 4-dinitrophenyl)-aminopropanoate crystals,” Phys. Rev. A 26, 2016–2027 (1982).

J. Zyss, D. S. Chemla, and J. F. Nicoud, “Demonstration of efficient nonlinear optical crystals with vanishing molecular dipole moment: second-harmonic generation in 3-methyl-4-nitropyridine-1-oxide,” J. Chem. Phys. 74, 4800–4811 (1981).

J. Zyss, “Hyperpolarizabilities of substituted conjugated molecules. II. Substituent effects and respective σ–π contributions,” J. Chem. Phys. 70, 3341–3349 (1979).

Adv. Mater. (1)

J. Zyss, R. Masse, M. Bagieu-Beucher, and J. P. Lévy, “Quasi-perfect polar alignment of nonlinear chromophores in a crystalline H-bonded guest–host structure: 2-amino-5-nitropyridinium-L-monohydrogentartrate,” Adv. Mater. 5, 120–124 (1993).

Appl. Opt. (1)

Appl. Phys. Lett. (5)

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).

P. Günter, C. Bosshard, K. Sutter, H. Arend, G. Chapuis, R. J. Twieg, and D. Dobrowolski, “2-cyclooctylamino-5-nitropyridine, a new nonlinear optical crystal with orthorhombic symmetry,” Appl. Phys. Lett. 50, 486–488 (1987).

P. D. Southgate and D. S. Hall, “Anomalously high nonlinear optical effects in m-nitroaniline,” Appl. Phys. Lett. 18, 456–458 (1971).

R. Morita and P. V. Vidaković, “Angle and temperature tuning of phase-matched second-harmonic generation in N-(4-nitrophenyl)-N-methylaminoacetonitrile,” Appl. Phys. Lett. 61, 2854–2856 (1992).

J. D. Bierlein, L. K. Cheng, Y. Wand, and W. Tam, “Linear and nonlinear optical properties of 3-methyl-4-methoxy-4-nitrostilbene single crystals,” Appl. Phys. Lett. 56, 423–425 (1990).

IEEE J. Quantum Electron. (2)

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. P. Fève, B. Boulanger, I. Rousseau, G. Marnier, J. Zaccaro, and A. Ibanez, “Second-harmonic generation properties of 2-amino-5-nitropyridium-dihydrogenoarsenate and dihydrogenophosphate organic–inorganic crystals,” IEEE J. Quantum Electron. 35, 66–71 (1999).

J. Appl. Phys. (1)

J. L. Oudar and R. Hierle, “An efficient organic crystal for nonlinear optics: methyl-(2, 4-dinitrophenyl)-aminopropanoate,” J. Appl. Phys. 48, 2699–2704 (1977).

J. Chem. Phys. (5)

J. Zyss, D. S. Chemla, and J. F. Nicoud, “Demonstration of efficient nonlinear optical crystals with vanishing molecular dipole moment: second-harmonic generation in 3-methyl-4-nitropyridine-1-oxide,” J. Chem. Phys. 74, 4800–4811 (1981).

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

J. Zyss, “Hyperpolarizabilities of substituted conjugated molecules. II. Substituent effects and respective σ–π contributions,” J. Chem. Phys. 70, 3341–3349 (1979).

J. Zyss, S. Brasselet, V. R. Thalladi, and G. R. Desiraju, “Octupolar versus dipolar crystalline structures for nonlinear optics: a dual crystal and propagative engineering approach,” J. Chem. Phys. 109, 658–669 (1998).

J. Zyss, J. F. Nicoud, and M. Coquillay, “Chirality and hydrogen bonding in molecular crystals for phase-matched second-harmonic generation: N-(4-nitrophenyl)-(L)-prolinol (NPP),” J. Chem. Phys. 81, 4160–4167 (1984).

J. Cryst. Growth (1)

N. Horiuchi, F. Lefaucheux, M. C. Robert, D. Josse, S. Khodja, and J. Zyss, “Gel growth of 2-amino-5-nitropyridinium dihydrogen phosphate organomineral crystals: x-ray and nonlinear optics characterization,” J. Cryst. Growth 147, 361–368 (1995).

J. Mater. Chem. (2)

J. F. Nicoud, R. Masse, C. Bourgogne, and C. Evans, “Perfect layered arrangement of ion-paired chromophores in a crystalline non-linear optical organic salt: 2-amino-3-nitropyridinium chloride,” J. Mater. Chem. 7, 35–39 (1997).

J. Pécaut, J. P. Lévy, and R. Masse, “Structural evidence in 2-amino-5-nitropyridinium halides (Cl, Br) of herringbone motifs favourable to efficient quadratic non-linear optical properties,” J. Mater. Chem. 3, 999–1003 (1993).

J. Opt. Mater. (1)

N. Horiuchi, F. Lefaucheux, A. Ibanez, D. Josse, and J. Zyss, “An organic-inorganic crystal for blue SHG: crystal growth and quadratic optical effect on 2-amino-5-nitropyrinium chloride,” J. Opt. Mater. 12, 351–356 (1999).

J. Opt. Soc. Am. B (3)

J. Phys. B (1)

F. Béhat 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).

J. Solid State Chem. (1)

A. Ibanez, J. P. Lévy, C. Mouget, and E. Prieur, “Crystal growth of a promising nonlinear optical material: 2-amino-5-nitropyridinium-chloride,” J. Solid State Chem. 129, 22–29 (1997).

Mol. Eng. (1)

R. Masse and J. Zyss, “A new approach in the design of polar crystals for quadratic nonlinear optics exemplified by the synthesis of 2-amino-5-nitropyridium-dihydrogen monophosphate (2A5NPDP),” Mol. Eng. 1, 141–152 (1991).

Nonlinear Opt. (2)

R. Masse, M. Bagieu-Beucher, J. Pécaut, J. P. Lévy, and J. Zyss, “Design of organic–inorganic polar crystals for quadratic nonlinear optics,” Nonlinear Opt. 5, 413–423 (1993).

J. Zyss, “Octupolar organic systems in quadratic nonlinear optics: molecules and materials,” Nonlinear Opt. 1, 3–18 (1991).

Opt. Commun. (1)

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

Phys. Rev. A (2)

J. L. Oudar and J. Zyss, “Structural dependence of nonlinear-optical properties of methyl-(2, 4-dinitrophenyl)-aminopropanoate crystals,” Phys. Rev. A 26, 2016–2027 (1982).

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

Other (4)

J. Zyss and D. S. Chemla, eds., Nonlinear Optical Properties of Organic Molecules and Crystals (Academic, Orlando, Fla., 1987).

J. Zyss, ed., Molecular Nonlinear Optics: Materials Physics and Devices (Academic, New York, 1994).

A. Yariv, Quantum Electronics (Wiley, New York, 1988).

W. Koechner, ed., Solid-State Laser Engineering, Springer Series of Optical Science (Springer-Verlag, Berlin, 1988), Vol. 1.

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