Abstract

Hexadecakis(2,2,2-trifluoroethoxy)-substituted vanadyl and zinc phthalocyanines, and hexadecakis(ethoxy)vanadylphthalocyanine, were synthesized and characterized. Their aggregation properties were studied by evaluation of the concentration dependence of absorption spectra. Hexadecakis(2,2,2-trifluoroethoxy)-substituted metallophthalocyanines were found to be nonaggregated phthalocyanines even in the condensed state. However, nonfluorinated hexadecakis(ethoxy)vanadylphthalocyanine showed a redshift of the Q band in the solid state. The third-order nonlinear optical properties of these phthalocyanine films were studied by electroabsorption measurement in terms of molecular structure and aggregation. The aggregation effect enhances the macroscopic third-order nonlinearity of metallophthalocyanine. Among nonaggregated hexadecakis(2,2,2-trifluoroethoxy)-substituted metallophthalocyanines, zinc phthalocyanine was found to have a larger macroscopic third-order nonlinearity than the vanadyl compound.

© 1998 Optical Society of America

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    [CrossRef]
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    [CrossRef]
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    [CrossRef]
  35. J. W. Wu, J. R. Heflin, R. A. Norwood, K. Y. Wong, O. Zamani-Khamiri, A. F. Garito, P. Kalyanaraman, and J. Sounik, “Nonlinear-optical processes in low-dimensional conjugated structures,” J. Opt. Soc. Am. B 6, 707–720 (1989).
    [CrossRef]

1996 (4)

M. A. Díaz-García, J. M. Cabrera, F. Agulló-López, J. A. Duro, G. de la Torre, T. Torres, F. Fernández-Lázaro, P. Delhaes, and C. Mingotaud, “Third-order nonlinear optical susceptibilities of the Langmuir–Blodgett films of octa-substituted metallophthalocyanines,” Appl. Phys. Lett. 69, 293–295 (1996).
[CrossRef]

S. L. Fang, H. Tada, and S. Mashiko, “Enhancement of the third-order nonlinear optical susceptibility in epitaxial vanadyl-phthalocyanine films grown on KBr,” Appl. Phys. Lett. 69, 767–769 (1996).
[CrossRef]

T. Isoshima, N. Pfeffer, M. Tian, T. Wada, and H. Sasabe, “Polarization dependence of transient absorption change in a vanadylphthalocyanine,” in Nonlinear Optical Properties of Organic Materials IX, G. R. Möhlmann, ed., Proc. SPIE 2852, 211–219 (1996).
[CrossRef]

J. W. Perry, K. Mansour, I.-Y. S. Lee, X.-L. Wu, P. V. Bedworth, C.-T. Chen, D. Ng, S. R. Marder, P. Miles, T. Wada, M. Tian, and H. Sasabe, “Organic optical limiter with a strong nonlinear absorptive response,” Science 273, 1533–1536 (1996).
[CrossRef]

1995 (2)

N. J. Long, “Organometallic compounds for nonlinear optics—the search for enlightenment,” Angew. Chem. Int. Ed. Engl. 34, 21–38 (1995).
[CrossRef]

H. Tajalli, J. P. Jiang, J. T. Murray, N. R. Armstrong, A. Schmidt, M. Chandross, S. Mazumdar, and N. Peyghambarian, “Spectra of third-order optical nonlinear susceptibilities of epitaxial chloro-indium-phthalocyanines,” Appl. Phys. Lett. 67, 1639–1641 (1995).
[CrossRef]

1994 (3)

J. L. Brédas, C. Adant, P. Tackx, and A. Persoons, “Third-order nonlinear optical response in organic materials: theoretical and experimental aspects,” Chem. Rev. 94, 243–278 (1994).
[CrossRef]

T. Wada and H. Sasabe, “Metallophthalocyanine: aggregation and nonlinear optics,” in Organic, Metallo-Organic, and Polymeric Materials for Nonlinear Optical Applications, S. R. Marder and J. W. Perry, eds., Proc. SPIE 2143, 164–171 (1994).
[CrossRef]

S. Yanagi, T. Wada, J. Kumar, H. Sasabe, and K. Sasaki, “Electroabsorption spectra and nonlinear optical susceptibility of tetrakis tert-butyl phthalocyanine,” Mol. Cryst. Liq. Cryst. 255, 167–175 (1994).
[CrossRef]

1993 (1)

H. S. Nalwa, A. Kakuta, and A. Mukoh, “Third-order optical nonlinearities of tetrakis-n-pentoxy carbonyl metallo-naphthalocyanines,” Chem. Phys. Lett. 203, 109–113 (1993).
[CrossRef]

1992 (2)

M. Hosoda, T. Wada, T. Yamamoto, A. Kaneko, A. F. Garito, and H. Sasabe, “Enhancement of third-order optical nonlinearities of soluble vanadyl phthalocyanines in doped polymer films,” Jpn. J. Appl. Phys. 31, 1071–1075 (1992).
[CrossRef]

A. Terasaki, M. Hosoda, T. Wada, H. Tada, A. Koma, A. Yamada, H. Sasabe, A. F. Garito, and T. Kobayashi, “Femtosecond spectroscopy of vanadyl phthalocyanines in various molecular arrangements,” J. Phys. Chem. 96, 10534–10542 (1992).
[CrossRef]

1991 (2)

M. Hosoda, T. Wada, A. Yamada, A. F. Garito, and H. Sasabe, “Phase and third-order optical nonlinearities in tetravalent metallophthalocyanine thin films,” Jpn. J. Appl. Phys. 30, L1486–L1488 (1991).
[CrossRef]

M. Hosoda, T. Wada, A. Yamada, A. F. Garito, and H. Sasabe, “Third-order nonlinear optical properties in soluble phthalocyanines with tert-butyl substituents,” Jpn. J. Appl. Phys. 30, 1715–1719 (1991).
[CrossRef]

1989 (3)

J. W. Wu, J. R. Heflin, R. A. Norwood, K. Y. Wong, O. Zamani-Khamiri, A. F. Garito, P. Kalyanaraman, and J. Sounik, “Nonlinear-optical processes in low-dimensional conjugated structures,” J. Opt. Soc. Am. B 6, 707–720 (1989).
[CrossRef]

T. Wada, Y. Matsuoka, K. Shigehara, A. Yamada, A. F. Garito, and H. Sasabe, “Organic nonlinear thin film: phthalocyanine derivatives,” in Photoresponsive Materials, M. Doyama, S. Somiya, R. P. H. Chang, and S. Tazuke, eds., Mater. Res. Soc. Symp. Proc. 12, 75–80 (1989).

R. Worland, S. D. Phillips, W. C. Walker, and A. J. Heeger, “Electroabsorption and nonlinear optical constants of trans-polyacetylene and poly(3-hexylthiophene),” Synth. Met. 28, D663–D667 (1989).
[CrossRef]

1988 (2)

M. Sinclair, D. Moses, K. Agagi, and A. J. Heeger, “Aniso-tropy of the third-order nonlinear optical susceptibility in a degenerate-ground-state conjugated polymer: trans- (CH)x,” Phys. Rev. B 38, 10724–10733 (1988).
[CrossRef]

J. R. Heflin, K. Y. Wong, O. Zamani-Khamiri, and A. F. Garito, “Nonlinear optical properties of linear chains and electron-correlation effects,” Phys. Rev. B 38, 1573–1576 (1988).
[CrossRef]

1987 (2)

J. S. Weiner, D. A. B. Miller, and D. S. Chemla, “Quadratic electro-optic effect due to the quantum-confined Stark effect in quantum wells,” Appl. Phys. Lett. 50, 842–844 (1987).
[CrossRef]

Z. Z. Ho, C. Y. Ju, and W. M. Hetherington III, “Third harmonic generation in phthalocyanines,” J. Appl. Phys. 62, 716–718 (1987).
[CrossRef]

1985 (1)

E. S. Dodsworth, A. B. P. Lever, P. Seymour, and C. C. Leznoff, “Intramolecular coupling in metal-free binuclear phthalocyanine,” J. Phys. Chem. 89, 5698–5705 (1985).
[CrossRef]

1981 (1)

T. G. Arkatova, N. M. Gopshtein, E. G. Makarova, and B. A. Mikhailov, “Determining the optical constants of a material by means of the Kramers–Kronig relations,” Sov. J. Opt. Technol. 48, 552–562 (1981).

1980 (1)

H. Tomoda, S. Saito, S. Ogawa, and S. Shiraishi, “Synthesis of phthalocyanines from phthalonitrile with organic strong base,” Chem. Lett. 1277–1280 (1980).
[CrossRef]

1978 (1)

G. A. Agrawal, C. Cojan, and C. Flytzanis, “Nonlinear optical properties of one-dimensional semiconductors and conjugated polymers,” Phys. Rev. B 17, 776–789 (1978).
[CrossRef]

1977 (1)

M. Gouterman, D. Holten, and E. Lieberman, “Porphyrins XXXV. Exciton coupling in μ-oxo scandium dimers,” Chem. Phys. 25, 139–153 (1977).
[CrossRef]

1973 (1)

A. M. Schaffer, M. Gouterman, and E. R. Davidson, “Porphyrins XXVIII. Extended Hückel calculations on metal phthalocyanines and tetrazaporphyrins,” Theor. Chim. Acta 30, 9–30 (1973).
[CrossRef]

1972 (1)

A. J. McHugh, M. Gouterman, and C. Weiss, “Porphyrins XXIV. Energy, oscillator strength, and Zeeman splitting calculations (SCMO-CI) for phthalocyanine, porphyrins and related ring systems,” Theor. Chim. Acta 24, 346–370 (1972).
[CrossRef]

1965 (1)

M. Kasha, H. R. Rawls, and M. A. El-Bayoumi, “The exciton model in molecular spectroscopy,” Pure Appl. Chem. 11, 371–392 (1965).
[CrossRef]

Adant, C.

J. L. Brédas, C. Adant, P. Tackx, and A. Persoons, “Third-order nonlinear optical response in organic materials: theoretical and experimental aspects,” Chem. Rev. 94, 243–278 (1994).
[CrossRef]

Agagi, K.

M. Sinclair, D. Moses, K. Agagi, and A. J. Heeger, “Aniso-tropy of the third-order nonlinear optical susceptibility in a degenerate-ground-state conjugated polymer: trans- (CH)x,” Phys. Rev. B 38, 10724–10733 (1988).
[CrossRef]

Agrawal, G. A.

G. A. Agrawal, C. Cojan, and C. Flytzanis, “Nonlinear optical properties of one-dimensional semiconductors and conjugated polymers,” Phys. Rev. B 17, 776–789 (1978).
[CrossRef]

Agulló-López, F.

M. A. Díaz-García, J. M. Cabrera, F. Agulló-López, J. A. Duro, G. de la Torre, T. Torres, F. Fernández-Lázaro, P. Delhaes, and C. Mingotaud, “Third-order nonlinear optical susceptibilities of the Langmuir–Blodgett films of octa-substituted metallophthalocyanines,” Appl. Phys. Lett. 69, 293–295 (1996).
[CrossRef]

Arkatova, T. G.

T. G. Arkatova, N. M. Gopshtein, E. G. Makarova, and B. A. Mikhailov, “Determining the optical constants of a material by means of the Kramers–Kronig relations,” Sov. J. Opt. Technol. 48, 552–562 (1981).

Armstrong, N. R.

H. Tajalli, J. P. Jiang, J. T. Murray, N. R. Armstrong, A. Schmidt, M. Chandross, S. Mazumdar, and N. Peyghambarian, “Spectra of third-order optical nonlinear susceptibilities of epitaxial chloro-indium-phthalocyanines,” Appl. Phys. Lett. 67, 1639–1641 (1995).
[CrossRef]

Bedworth, P. V.

J. W. Perry, K. Mansour, I.-Y. S. Lee, X.-L. Wu, P. V. Bedworth, C.-T. Chen, D. Ng, S. R. Marder, P. Miles, T. Wada, M. Tian, and H. Sasabe, “Organic optical limiter with a strong nonlinear absorptive response,” Science 273, 1533–1536 (1996).
[CrossRef]

Brédas, J. L.

J. L. Brédas, C. Adant, P. Tackx, and A. Persoons, “Third-order nonlinear optical response in organic materials: theoretical and experimental aspects,” Chem. Rev. 94, 243–278 (1994).
[CrossRef]

Cabrera, J. M.

M. A. Díaz-García, J. M. Cabrera, F. Agulló-López, J. A. Duro, G. de la Torre, T. Torres, F. Fernández-Lázaro, P. Delhaes, and C. Mingotaud, “Third-order nonlinear optical susceptibilities of the Langmuir–Blodgett films of octa-substituted metallophthalocyanines,” Appl. Phys. Lett. 69, 293–295 (1996).
[CrossRef]

Chandross, M.

H. Tajalli, J. P. Jiang, J. T. Murray, N. R. Armstrong, A. Schmidt, M. Chandross, S. Mazumdar, and N. Peyghambarian, “Spectra of third-order optical nonlinear susceptibilities of epitaxial chloro-indium-phthalocyanines,” Appl. Phys. Lett. 67, 1639–1641 (1995).
[CrossRef]

Chemla, D. S.

J. S. Weiner, D. A. B. Miller, and D. S. Chemla, “Quadratic electro-optic effect due to the quantum-confined Stark effect in quantum wells,” Appl. Phys. Lett. 50, 842–844 (1987).
[CrossRef]

Chen, C.-T.

J. W. Perry, K. Mansour, I.-Y. S. Lee, X.-L. Wu, P. V. Bedworth, C.-T. Chen, D. Ng, S. R. Marder, P. Miles, T. Wada, M. Tian, and H. Sasabe, “Organic optical limiter with a strong nonlinear absorptive response,” Science 273, 1533–1536 (1996).
[CrossRef]

Cojan, C.

G. A. Agrawal, C. Cojan, and C. Flytzanis, “Nonlinear optical properties of one-dimensional semiconductors and conjugated polymers,” Phys. Rev. B 17, 776–789 (1978).
[CrossRef]

Davidson, E. R.

A. M. Schaffer, M. Gouterman, and E. R. Davidson, “Porphyrins XXVIII. Extended Hückel calculations on metal phthalocyanines and tetrazaporphyrins,” Theor. Chim. Acta 30, 9–30 (1973).
[CrossRef]

de la Torre, G.

M. A. Díaz-García, J. M. Cabrera, F. Agulló-López, J. A. Duro, G. de la Torre, T. Torres, F. Fernández-Lázaro, P. Delhaes, and C. Mingotaud, “Third-order nonlinear optical susceptibilities of the Langmuir–Blodgett films of octa-substituted metallophthalocyanines,” Appl. Phys. Lett. 69, 293–295 (1996).
[CrossRef]

Delhaes, P.

M. A. Díaz-García, J. M. Cabrera, F. Agulló-López, J. A. Duro, G. de la Torre, T. Torres, F. Fernández-Lázaro, P. Delhaes, and C. Mingotaud, “Third-order nonlinear optical susceptibilities of the Langmuir–Blodgett films of octa-substituted metallophthalocyanines,” Appl. Phys. Lett. 69, 293–295 (1996).
[CrossRef]

Díaz-García, M. A.

M. A. Díaz-García, J. M. Cabrera, F. Agulló-López, J. A. Duro, G. de la Torre, T. Torres, F. Fernández-Lázaro, P. Delhaes, and C. Mingotaud, “Third-order nonlinear optical susceptibilities of the Langmuir–Blodgett films of octa-substituted metallophthalocyanines,” Appl. Phys. Lett. 69, 293–295 (1996).
[CrossRef]

Dodsworth, E. S.

E. S. Dodsworth, A. B. P. Lever, P. Seymour, and C. C. Leznoff, “Intramolecular coupling in metal-free binuclear phthalocyanine,” J. Phys. Chem. 89, 5698–5705 (1985).
[CrossRef]

Duro, J. A.

M. A. Díaz-García, J. M. Cabrera, F. Agulló-López, J. A. Duro, G. de la Torre, T. Torres, F. Fernández-Lázaro, P. Delhaes, and C. Mingotaud, “Third-order nonlinear optical susceptibilities of the Langmuir–Blodgett films of octa-substituted metallophthalocyanines,” Appl. Phys. Lett. 69, 293–295 (1996).
[CrossRef]

El-Bayoumi, M. A.

M. Kasha, H. R. Rawls, and M. A. El-Bayoumi, “The exciton model in molecular spectroscopy,” Pure Appl. Chem. 11, 371–392 (1965).
[CrossRef]

Fang, S. L.

S. L. Fang, H. Tada, and S. Mashiko, “Enhancement of the third-order nonlinear optical susceptibility in epitaxial vanadyl-phthalocyanine films grown on KBr,” Appl. Phys. Lett. 69, 767–769 (1996).
[CrossRef]

Fernández-Lázaro, F.

M. A. Díaz-García, J. M. Cabrera, F. Agulló-López, J. A. Duro, G. de la Torre, T. Torres, F. Fernández-Lázaro, P. Delhaes, and C. Mingotaud, “Third-order nonlinear optical susceptibilities of the Langmuir–Blodgett films of octa-substituted metallophthalocyanines,” Appl. Phys. Lett. 69, 293–295 (1996).
[CrossRef]

Flytzanis, C.

G. A. Agrawal, C. Cojan, and C. Flytzanis, “Nonlinear optical properties of one-dimensional semiconductors and conjugated polymers,” Phys. Rev. B 17, 776–789 (1978).
[CrossRef]

Garito, A. F.

M. Hosoda, T. Wada, T. Yamamoto, A. Kaneko, A. F. Garito, and H. Sasabe, “Enhancement of third-order optical nonlinearities of soluble vanadyl phthalocyanines in doped polymer films,” Jpn. J. Appl. Phys. 31, 1071–1075 (1992).
[CrossRef]

A. Terasaki, M. Hosoda, T. Wada, H. Tada, A. Koma, A. Yamada, H. Sasabe, A. F. Garito, and T. Kobayashi, “Femtosecond spectroscopy of vanadyl phthalocyanines in various molecular arrangements,” J. Phys. Chem. 96, 10534–10542 (1992).
[CrossRef]

M. Hosoda, T. Wada, A. Yamada, A. F. Garito, and H. Sasabe, “Phase and third-order optical nonlinearities in tetravalent metallophthalocyanine thin films,” Jpn. J. Appl. Phys. 30, L1486–L1488 (1991).
[CrossRef]

M. Hosoda, T. Wada, A. Yamada, A. F. Garito, and H. Sasabe, “Third-order nonlinear optical properties in soluble phthalocyanines with tert-butyl substituents,” Jpn. J. Appl. Phys. 30, 1715–1719 (1991).
[CrossRef]

J. W. Wu, J. R. Heflin, R. A. Norwood, K. Y. Wong, O. Zamani-Khamiri, A. F. Garito, P. Kalyanaraman, and J. Sounik, “Nonlinear-optical processes in low-dimensional conjugated structures,” J. Opt. Soc. Am. B 6, 707–720 (1989).
[CrossRef]

T. Wada, Y. Matsuoka, K. Shigehara, A. Yamada, A. F. Garito, and H. Sasabe, “Organic nonlinear thin film: phthalocyanine derivatives,” in Photoresponsive Materials, M. Doyama, S. Somiya, R. P. H. Chang, and S. Tazuke, eds., Mater. Res. Soc. Symp. Proc. 12, 75–80 (1989).

J. R. Heflin, K. Y. Wong, O. Zamani-Khamiri, and A. F. Garito, “Nonlinear optical properties of linear chains and electron-correlation effects,” Phys. Rev. B 38, 1573–1576 (1988).
[CrossRef]

Gopshtein, N. M.

T. G. Arkatova, N. M. Gopshtein, E. G. Makarova, and B. A. Mikhailov, “Determining the optical constants of a material by means of the Kramers–Kronig relations,” Sov. J. Opt. Technol. 48, 552–562 (1981).

Gouterman, M.

M. Gouterman, D. Holten, and E. Lieberman, “Porphyrins XXXV. Exciton coupling in μ-oxo scandium dimers,” Chem. Phys. 25, 139–153 (1977).
[CrossRef]

A. M. Schaffer, M. Gouterman, and E. R. Davidson, “Porphyrins XXVIII. Extended Hückel calculations on metal phthalocyanines and tetrazaporphyrins,” Theor. Chim. Acta 30, 9–30 (1973).
[CrossRef]

A. J. McHugh, M. Gouterman, and C. Weiss, “Porphyrins XXIV. Energy, oscillator strength, and Zeeman splitting calculations (SCMO-CI) for phthalocyanine, porphyrins and related ring systems,” Theor. Chim. Acta 24, 346–370 (1972).
[CrossRef]

Heeger, A. J.

R. Worland, S. D. Phillips, W. C. Walker, and A. J. Heeger, “Electroabsorption and nonlinear optical constants of trans-polyacetylene and poly(3-hexylthiophene),” Synth. Met. 28, D663–D667 (1989).
[CrossRef]

M. Sinclair, D. Moses, K. Agagi, and A. J. Heeger, “Aniso-tropy of the third-order nonlinear optical susceptibility in a degenerate-ground-state conjugated polymer: trans- (CH)x,” Phys. Rev. B 38, 10724–10733 (1988).
[CrossRef]

Heflin, J. R.

J. W. Wu, J. R. Heflin, R. A. Norwood, K. Y. Wong, O. Zamani-Khamiri, A. F. Garito, P. Kalyanaraman, and J. Sounik, “Nonlinear-optical processes in low-dimensional conjugated structures,” J. Opt. Soc. Am. B 6, 707–720 (1989).
[CrossRef]

J. R. Heflin, K. Y. Wong, O. Zamani-Khamiri, and A. F. Garito, “Nonlinear optical properties of linear chains and electron-correlation effects,” Phys. Rev. B 38, 1573–1576 (1988).
[CrossRef]

Hetherington III, W. M.

Z. Z. Ho, C. Y. Ju, and W. M. Hetherington III, “Third harmonic generation in phthalocyanines,” J. Appl. Phys. 62, 716–718 (1987).
[CrossRef]

Ho, Z. Z.

Z. Z. Ho, C. Y. Ju, and W. M. Hetherington III, “Third harmonic generation in phthalocyanines,” J. Appl. Phys. 62, 716–718 (1987).
[CrossRef]

Holten, D.

M. Gouterman, D. Holten, and E. Lieberman, “Porphyrins XXXV. Exciton coupling in μ-oxo scandium dimers,” Chem. Phys. 25, 139–153 (1977).
[CrossRef]

Hosoda, M.

M. Hosoda, T. Wada, T. Yamamoto, A. Kaneko, A. F. Garito, and H. Sasabe, “Enhancement of third-order optical nonlinearities of soluble vanadyl phthalocyanines in doped polymer films,” Jpn. J. Appl. Phys. 31, 1071–1075 (1992).
[CrossRef]

A. Terasaki, M. Hosoda, T. Wada, H. Tada, A. Koma, A. Yamada, H. Sasabe, A. F. Garito, and T. Kobayashi, “Femtosecond spectroscopy of vanadyl phthalocyanines in various molecular arrangements,” J. Phys. Chem. 96, 10534–10542 (1992).
[CrossRef]

M. Hosoda, T. Wada, A. Yamada, A. F. Garito, and H. Sasabe, “Phase and third-order optical nonlinearities in tetravalent metallophthalocyanine thin films,” Jpn. J. Appl. Phys. 30, L1486–L1488 (1991).
[CrossRef]

M. Hosoda, T. Wada, A. Yamada, A. F. Garito, and H. Sasabe, “Third-order nonlinear optical properties in soluble phthalocyanines with tert-butyl substituents,” Jpn. J. Appl. Phys. 30, 1715–1719 (1991).
[CrossRef]

Isoshima, T.

T. Isoshima, N. Pfeffer, M. Tian, T. Wada, and H. Sasabe, “Polarization dependence of transient absorption change in a vanadylphthalocyanine,” in Nonlinear Optical Properties of Organic Materials IX, G. R. Möhlmann, ed., Proc. SPIE 2852, 211–219 (1996).
[CrossRef]

Jiang, J. P.

H. Tajalli, J. P. Jiang, J. T. Murray, N. R. Armstrong, A. Schmidt, M. Chandross, S. Mazumdar, and N. Peyghambarian, “Spectra of third-order optical nonlinear susceptibilities of epitaxial chloro-indium-phthalocyanines,” Appl. Phys. Lett. 67, 1639–1641 (1995).
[CrossRef]

Ju, C. Y.

Z. Z. Ho, C. Y. Ju, and W. M. Hetherington III, “Third harmonic generation in phthalocyanines,” J. Appl. Phys. 62, 716–718 (1987).
[CrossRef]

Kakuta, A.

H. S. Nalwa, A. Kakuta, and A. Mukoh, “Third-order optical nonlinearities of tetrakis-n-pentoxy carbonyl metallo-naphthalocyanines,” Chem. Phys. Lett. 203, 109–113 (1993).
[CrossRef]

Kalyanaraman, P.

Kaneko, A.

M. Hosoda, T. Wada, T. Yamamoto, A. Kaneko, A. F. Garito, and H. Sasabe, “Enhancement of third-order optical nonlinearities of soluble vanadyl phthalocyanines in doped polymer films,” Jpn. J. Appl. Phys. 31, 1071–1075 (1992).
[CrossRef]

Kasha, M.

M. Kasha, H. R. Rawls, and M. A. El-Bayoumi, “The exciton model in molecular spectroscopy,” Pure Appl. Chem. 11, 371–392 (1965).
[CrossRef]

Kobayashi, T.

A. Terasaki, M. Hosoda, T. Wada, H. Tada, A. Koma, A. Yamada, H. Sasabe, A. F. Garito, and T. Kobayashi, “Femtosecond spectroscopy of vanadyl phthalocyanines in various molecular arrangements,” J. Phys. Chem. 96, 10534–10542 (1992).
[CrossRef]

Koma, A.

A. Terasaki, M. Hosoda, T. Wada, H. Tada, A. Koma, A. Yamada, H. Sasabe, A. F. Garito, and T. Kobayashi, “Femtosecond spectroscopy of vanadyl phthalocyanines in various molecular arrangements,” J. Phys. Chem. 96, 10534–10542 (1992).
[CrossRef]

Kumar, J.

S. Yanagi, T. Wada, J. Kumar, H. Sasabe, and K. Sasaki, “Electroabsorption spectra and nonlinear optical susceptibility of tetrakis tert-butyl phthalocyanine,” Mol. Cryst. Liq. Cryst. 255, 167–175 (1994).
[CrossRef]

Lee, I.-Y. S.

J. W. Perry, K. Mansour, I.-Y. S. Lee, X.-L. Wu, P. V. Bedworth, C.-T. Chen, D. Ng, S. R. Marder, P. Miles, T. Wada, M. Tian, and H. Sasabe, “Organic optical limiter with a strong nonlinear absorptive response,” Science 273, 1533–1536 (1996).
[CrossRef]

Lever, A. B. P.

E. S. Dodsworth, A. B. P. Lever, P. Seymour, and C. C. Leznoff, “Intramolecular coupling in metal-free binuclear phthalocyanine,” J. Phys. Chem. 89, 5698–5705 (1985).
[CrossRef]

Leznoff, C. C.

E. S. Dodsworth, A. B. P. Lever, P. Seymour, and C. C. Leznoff, “Intramolecular coupling in metal-free binuclear phthalocyanine,” J. Phys. Chem. 89, 5698–5705 (1985).
[CrossRef]

Lieberman, E.

M. Gouterman, D. Holten, and E. Lieberman, “Porphyrins XXXV. Exciton coupling in μ-oxo scandium dimers,” Chem. Phys. 25, 139–153 (1977).
[CrossRef]

Long, N. J.

N. J. Long, “Organometallic compounds for nonlinear optics—the search for enlightenment,” Angew. Chem. Int. Ed. Engl. 34, 21–38 (1995).
[CrossRef]

Makarova, E. G.

T. G. Arkatova, N. M. Gopshtein, E. G. Makarova, and B. A. Mikhailov, “Determining the optical constants of a material by means of the Kramers–Kronig relations,” Sov. J. Opt. Technol. 48, 552–562 (1981).

Mansour, K.

J. W. Perry, K. Mansour, I.-Y. S. Lee, X.-L. Wu, P. V. Bedworth, C.-T. Chen, D. Ng, S. R. Marder, P. Miles, T. Wada, M. Tian, and H. Sasabe, “Organic optical limiter with a strong nonlinear absorptive response,” Science 273, 1533–1536 (1996).
[CrossRef]

Marder, S. R.

J. W. Perry, K. Mansour, I.-Y. S. Lee, X.-L. Wu, P. V. Bedworth, C.-T. Chen, D. Ng, S. R. Marder, P. Miles, T. Wada, M. Tian, and H. Sasabe, “Organic optical limiter with a strong nonlinear absorptive response,” Science 273, 1533–1536 (1996).
[CrossRef]

Mashiko, S.

S. L. Fang, H. Tada, and S. Mashiko, “Enhancement of the third-order nonlinear optical susceptibility in epitaxial vanadyl-phthalocyanine films grown on KBr,” Appl. Phys. Lett. 69, 767–769 (1996).
[CrossRef]

Matsuoka, Y.

T. Wada, Y. Matsuoka, K. Shigehara, A. Yamada, A. F. Garito, and H. Sasabe, “Organic nonlinear thin film: phthalocyanine derivatives,” in Photoresponsive Materials, M. Doyama, S. Somiya, R. P. H. Chang, and S. Tazuke, eds., Mater. Res. Soc. Symp. Proc. 12, 75–80 (1989).

Mazumdar, S.

H. Tajalli, J. P. Jiang, J. T. Murray, N. R. Armstrong, A. Schmidt, M. Chandross, S. Mazumdar, and N. Peyghambarian, “Spectra of third-order optical nonlinear susceptibilities of epitaxial chloro-indium-phthalocyanines,” Appl. Phys. Lett. 67, 1639–1641 (1995).
[CrossRef]

McHugh, A. J.

A. J. McHugh, M. Gouterman, and C. Weiss, “Porphyrins XXIV. Energy, oscillator strength, and Zeeman splitting calculations (SCMO-CI) for phthalocyanine, porphyrins and related ring systems,” Theor. Chim. Acta 24, 346–370 (1972).
[CrossRef]

Mikhailov, B. A.

T. G. Arkatova, N. M. Gopshtein, E. G. Makarova, and B. A. Mikhailov, “Determining the optical constants of a material by means of the Kramers–Kronig relations,” Sov. J. Opt. Technol. 48, 552–562 (1981).

Miles, P.

J. W. Perry, K. Mansour, I.-Y. S. Lee, X.-L. Wu, P. V. Bedworth, C.-T. Chen, D. Ng, S. R. Marder, P. Miles, T. Wada, M. Tian, and H. Sasabe, “Organic optical limiter with a strong nonlinear absorptive response,” Science 273, 1533–1536 (1996).
[CrossRef]

Miller, D. A. B.

J. S. Weiner, D. A. B. Miller, and D. S. Chemla, “Quadratic electro-optic effect due to the quantum-confined Stark effect in quantum wells,” Appl. Phys. Lett. 50, 842–844 (1987).
[CrossRef]

Mingotaud, C.

M. A. Díaz-García, J. M. Cabrera, F. Agulló-López, J. A. Duro, G. de la Torre, T. Torres, F. Fernández-Lázaro, P. Delhaes, and C. Mingotaud, “Third-order nonlinear optical susceptibilities of the Langmuir–Blodgett films of octa-substituted metallophthalocyanines,” Appl. Phys. Lett. 69, 293–295 (1996).
[CrossRef]

Moses, D.

M. Sinclair, D. Moses, K. Agagi, and A. J. Heeger, “Aniso-tropy of the third-order nonlinear optical susceptibility in a degenerate-ground-state conjugated polymer: trans- (CH)x,” Phys. Rev. B 38, 10724–10733 (1988).
[CrossRef]

Mukoh, A.

H. S. Nalwa, A. Kakuta, and A. Mukoh, “Third-order optical nonlinearities of tetrakis-n-pentoxy carbonyl metallo-naphthalocyanines,” Chem. Phys. Lett. 203, 109–113 (1993).
[CrossRef]

Murray, J. T.

H. Tajalli, J. P. Jiang, J. T. Murray, N. R. Armstrong, A. Schmidt, M. Chandross, S. Mazumdar, and N. Peyghambarian, “Spectra of third-order optical nonlinear susceptibilities of epitaxial chloro-indium-phthalocyanines,” Appl. Phys. Lett. 67, 1639–1641 (1995).
[CrossRef]

Nalwa, H. S.

H. S. Nalwa, A. Kakuta, and A. Mukoh, “Third-order optical nonlinearities of tetrakis-n-pentoxy carbonyl metallo-naphthalocyanines,” Chem. Phys. Lett. 203, 109–113 (1993).
[CrossRef]

Ng, D.

J. W. Perry, K. Mansour, I.-Y. S. Lee, X.-L. Wu, P. V. Bedworth, C.-T. Chen, D. Ng, S. R. Marder, P. Miles, T. Wada, M. Tian, and H. Sasabe, “Organic optical limiter with a strong nonlinear absorptive response,” Science 273, 1533–1536 (1996).
[CrossRef]

Norwood, R. A.

Ogawa, S.

H. Tomoda, S. Saito, S. Ogawa, and S. Shiraishi, “Synthesis of phthalocyanines from phthalonitrile with organic strong base,” Chem. Lett. 1277–1280 (1980).
[CrossRef]

Perry, J. W.

J. W. Perry, K. Mansour, I.-Y. S. Lee, X.-L. Wu, P. V. Bedworth, C.-T. Chen, D. Ng, S. R. Marder, P. Miles, T. Wada, M. Tian, and H. Sasabe, “Organic optical limiter with a strong nonlinear absorptive response,” Science 273, 1533–1536 (1996).
[CrossRef]

Persoons, A.

J. L. Brédas, C. Adant, P. Tackx, and A. Persoons, “Third-order nonlinear optical response in organic materials: theoretical and experimental aspects,” Chem. Rev. 94, 243–278 (1994).
[CrossRef]

Peyghambarian, N.

H. Tajalli, J. P. Jiang, J. T. Murray, N. R. Armstrong, A. Schmidt, M. Chandross, S. Mazumdar, and N. Peyghambarian, “Spectra of third-order optical nonlinear susceptibilities of epitaxial chloro-indium-phthalocyanines,” Appl. Phys. Lett. 67, 1639–1641 (1995).
[CrossRef]

Pfeffer, N.

T. Isoshima, N. Pfeffer, M. Tian, T. Wada, and H. Sasabe, “Polarization dependence of transient absorption change in a vanadylphthalocyanine,” in Nonlinear Optical Properties of Organic Materials IX, G. R. Möhlmann, ed., Proc. SPIE 2852, 211–219 (1996).
[CrossRef]

Phillips, S. D.

R. Worland, S. D. Phillips, W. C. Walker, and A. J. Heeger, “Electroabsorption and nonlinear optical constants of trans-polyacetylene and poly(3-hexylthiophene),” Synth. Met. 28, D663–D667 (1989).
[CrossRef]

Rawls, H. R.

M. Kasha, H. R. Rawls, and M. A. El-Bayoumi, “The exciton model in molecular spectroscopy,” Pure Appl. Chem. 11, 371–392 (1965).
[CrossRef]

Saito, S.

H. Tomoda, S. Saito, S. Ogawa, and S. Shiraishi, “Synthesis of phthalocyanines from phthalonitrile with organic strong base,” Chem. Lett. 1277–1280 (1980).
[CrossRef]

Sasabe, H.

J. W. Perry, K. Mansour, I.-Y. S. Lee, X.-L. Wu, P. V. Bedworth, C.-T. Chen, D. Ng, S. R. Marder, P. Miles, T. Wada, M. Tian, and H. Sasabe, “Organic optical limiter with a strong nonlinear absorptive response,” Science 273, 1533–1536 (1996).
[CrossRef]

T. Isoshima, N. Pfeffer, M. Tian, T. Wada, and H. Sasabe, “Polarization dependence of transient absorption change in a vanadylphthalocyanine,” in Nonlinear Optical Properties of Organic Materials IX, G. R. Möhlmann, ed., Proc. SPIE 2852, 211–219 (1996).
[CrossRef]

T. Wada and H. Sasabe, “Metallophthalocyanine: aggregation and nonlinear optics,” in Organic, Metallo-Organic, and Polymeric Materials for Nonlinear Optical Applications, S. R. Marder and J. W. Perry, eds., Proc. SPIE 2143, 164–171 (1994).
[CrossRef]

S. Yanagi, T. Wada, J. Kumar, H. Sasabe, and K. Sasaki, “Electroabsorption spectra and nonlinear optical susceptibility of tetrakis tert-butyl phthalocyanine,” Mol. Cryst. Liq. Cryst. 255, 167–175 (1994).
[CrossRef]

A. Terasaki, M. Hosoda, T. Wada, H. Tada, A. Koma, A. Yamada, H. Sasabe, A. F. Garito, and T. Kobayashi, “Femtosecond spectroscopy of vanadyl phthalocyanines in various molecular arrangements,” J. Phys. Chem. 96, 10534–10542 (1992).
[CrossRef]

M. Hosoda, T. Wada, T. Yamamoto, A. Kaneko, A. F. Garito, and H. Sasabe, “Enhancement of third-order optical nonlinearities of soluble vanadyl phthalocyanines in doped polymer films,” Jpn. J. Appl. Phys. 31, 1071–1075 (1992).
[CrossRef]

M. Hosoda, T. Wada, A. Yamada, A. F. Garito, and H. Sasabe, “Phase and third-order optical nonlinearities in tetravalent metallophthalocyanine thin films,” Jpn. J. Appl. Phys. 30, L1486–L1488 (1991).
[CrossRef]

M. Hosoda, T. Wada, A. Yamada, A. F. Garito, and H. Sasabe, “Third-order nonlinear optical properties in soluble phthalocyanines with tert-butyl substituents,” Jpn. J. Appl. Phys. 30, 1715–1719 (1991).
[CrossRef]

T. Wada, Y. Matsuoka, K. Shigehara, A. Yamada, A. F. Garito, and H. Sasabe, “Organic nonlinear thin film: phthalocyanine derivatives,” in Photoresponsive Materials, M. Doyama, S. Somiya, R. P. H. Chang, and S. Tazuke, eds., Mater. Res. Soc. Symp. Proc. 12, 75–80 (1989).

Sasaki, K.

S. Yanagi, T. Wada, J. Kumar, H. Sasabe, and K. Sasaki, “Electroabsorption spectra and nonlinear optical susceptibility of tetrakis tert-butyl phthalocyanine,” Mol. Cryst. Liq. Cryst. 255, 167–175 (1994).
[CrossRef]

Schaffer, A. M.

A. M. Schaffer, M. Gouterman, and E. R. Davidson, “Porphyrins XXVIII. Extended Hückel calculations on metal phthalocyanines and tetrazaporphyrins,” Theor. Chim. Acta 30, 9–30 (1973).
[CrossRef]

Schmidt, A.

H. Tajalli, J. P. Jiang, J. T. Murray, N. R. Armstrong, A. Schmidt, M. Chandross, S. Mazumdar, and N. Peyghambarian, “Spectra of third-order optical nonlinear susceptibilities of epitaxial chloro-indium-phthalocyanines,” Appl. Phys. Lett. 67, 1639–1641 (1995).
[CrossRef]

Seymour, P.

E. S. Dodsworth, A. B. P. Lever, P. Seymour, and C. C. Leznoff, “Intramolecular coupling in metal-free binuclear phthalocyanine,” J. Phys. Chem. 89, 5698–5705 (1985).
[CrossRef]

Shigehara, K.

T. Wada, Y. Matsuoka, K. Shigehara, A. Yamada, A. F. Garito, and H. Sasabe, “Organic nonlinear thin film: phthalocyanine derivatives,” in Photoresponsive Materials, M. Doyama, S. Somiya, R. P. H. Chang, and S. Tazuke, eds., Mater. Res. Soc. Symp. Proc. 12, 75–80 (1989).

Shiraishi, S.

H. Tomoda, S. Saito, S. Ogawa, and S. Shiraishi, “Synthesis of phthalocyanines from phthalonitrile with organic strong base,” Chem. Lett. 1277–1280 (1980).
[CrossRef]

Sinclair, M.

M. Sinclair, D. Moses, K. Agagi, and A. J. Heeger, “Aniso-tropy of the third-order nonlinear optical susceptibility in a degenerate-ground-state conjugated polymer: trans- (CH)x,” Phys. Rev. B 38, 10724–10733 (1988).
[CrossRef]

Sounik, J.

Tackx, P.

J. L. Brédas, C. Adant, P. Tackx, and A. Persoons, “Third-order nonlinear optical response in organic materials: theoretical and experimental aspects,” Chem. Rev. 94, 243–278 (1994).
[CrossRef]

Tada, H.

S. L. Fang, H. Tada, and S. Mashiko, “Enhancement of the third-order nonlinear optical susceptibility in epitaxial vanadyl-phthalocyanine films grown on KBr,” Appl. Phys. Lett. 69, 767–769 (1996).
[CrossRef]

A. Terasaki, M. Hosoda, T. Wada, H. Tada, A. Koma, A. Yamada, H. Sasabe, A. F. Garito, and T. Kobayashi, “Femtosecond spectroscopy of vanadyl phthalocyanines in various molecular arrangements,” J. Phys. Chem. 96, 10534–10542 (1992).
[CrossRef]

Tajalli, H.

H. Tajalli, J. P. Jiang, J. T. Murray, N. R. Armstrong, A. Schmidt, M. Chandross, S. Mazumdar, and N. Peyghambarian, “Spectra of third-order optical nonlinear susceptibilities of epitaxial chloro-indium-phthalocyanines,” Appl. Phys. Lett. 67, 1639–1641 (1995).
[CrossRef]

Terasaki, A.

A. Terasaki, M. Hosoda, T. Wada, H. Tada, A. Koma, A. Yamada, H. Sasabe, A. F. Garito, and T. Kobayashi, “Femtosecond spectroscopy of vanadyl phthalocyanines in various molecular arrangements,” J. Phys. Chem. 96, 10534–10542 (1992).
[CrossRef]

Tian, M.

T. Isoshima, N. Pfeffer, M. Tian, T. Wada, and H. Sasabe, “Polarization dependence of transient absorption change in a vanadylphthalocyanine,” in Nonlinear Optical Properties of Organic Materials IX, G. R. Möhlmann, ed., Proc. SPIE 2852, 211–219 (1996).
[CrossRef]

J. W. Perry, K. Mansour, I.-Y. S. Lee, X.-L. Wu, P. V. Bedworth, C.-T. Chen, D. Ng, S. R. Marder, P. Miles, T. Wada, M. Tian, and H. Sasabe, “Organic optical limiter with a strong nonlinear absorptive response,” Science 273, 1533–1536 (1996).
[CrossRef]

Tomoda, H.

H. Tomoda, S. Saito, S. Ogawa, and S. Shiraishi, “Synthesis of phthalocyanines from phthalonitrile with organic strong base,” Chem. Lett. 1277–1280 (1980).
[CrossRef]

Torres, T.

M. A. Díaz-García, J. M. Cabrera, F. Agulló-López, J. A. Duro, G. de la Torre, T. Torres, F. Fernández-Lázaro, P. Delhaes, and C. Mingotaud, “Third-order nonlinear optical susceptibilities of the Langmuir–Blodgett films of octa-substituted metallophthalocyanines,” Appl. Phys. Lett. 69, 293–295 (1996).
[CrossRef]

Wada, T.

T. Isoshima, N. Pfeffer, M. Tian, T. Wada, and H. Sasabe, “Polarization dependence of transient absorption change in a vanadylphthalocyanine,” in Nonlinear Optical Properties of Organic Materials IX, G. R. Möhlmann, ed., Proc. SPIE 2852, 211–219 (1996).
[CrossRef]

J. W. Perry, K. Mansour, I.-Y. S. Lee, X.-L. Wu, P. V. Bedworth, C.-T. Chen, D. Ng, S. R. Marder, P. Miles, T. Wada, M. Tian, and H. Sasabe, “Organic optical limiter with a strong nonlinear absorptive response,” Science 273, 1533–1536 (1996).
[CrossRef]

S. Yanagi, T. Wada, J. Kumar, H. Sasabe, and K. Sasaki, “Electroabsorption spectra and nonlinear optical susceptibility of tetrakis tert-butyl phthalocyanine,” Mol. Cryst. Liq. Cryst. 255, 167–175 (1994).
[CrossRef]

T. Wada and H. Sasabe, “Metallophthalocyanine: aggregation and nonlinear optics,” in Organic, Metallo-Organic, and Polymeric Materials for Nonlinear Optical Applications, S. R. Marder and J. W. Perry, eds., Proc. SPIE 2143, 164–171 (1994).
[CrossRef]

M. Hosoda, T. Wada, T. Yamamoto, A. Kaneko, A. F. Garito, and H. Sasabe, “Enhancement of third-order optical nonlinearities of soluble vanadyl phthalocyanines in doped polymer films,” Jpn. J. Appl. Phys. 31, 1071–1075 (1992).
[CrossRef]

A. Terasaki, M. Hosoda, T. Wada, H. Tada, A. Koma, A. Yamada, H. Sasabe, A. F. Garito, and T. Kobayashi, “Femtosecond spectroscopy of vanadyl phthalocyanines in various molecular arrangements,” J. Phys. Chem. 96, 10534–10542 (1992).
[CrossRef]

M. Hosoda, T. Wada, A. Yamada, A. F. Garito, and H. Sasabe, “Phase and third-order optical nonlinearities in tetravalent metallophthalocyanine thin films,” Jpn. J. Appl. Phys. 30, L1486–L1488 (1991).
[CrossRef]

M. Hosoda, T. Wada, A. Yamada, A. F. Garito, and H. Sasabe, “Third-order nonlinear optical properties in soluble phthalocyanines with tert-butyl substituents,” Jpn. J. Appl. Phys. 30, 1715–1719 (1991).
[CrossRef]

T. Wada, Y. Matsuoka, K. Shigehara, A. Yamada, A. F. Garito, and H. Sasabe, “Organic nonlinear thin film: phthalocyanine derivatives,” in Photoresponsive Materials, M. Doyama, S. Somiya, R. P. H. Chang, and S. Tazuke, eds., Mater. Res. Soc. Symp. Proc. 12, 75–80 (1989).

Walker, W. C.

R. Worland, S. D. Phillips, W. C. Walker, and A. J. Heeger, “Electroabsorption and nonlinear optical constants of trans-polyacetylene and poly(3-hexylthiophene),” Synth. Met. 28, D663–D667 (1989).
[CrossRef]

Weiner, J. S.

J. S. Weiner, D. A. B. Miller, and D. S. Chemla, “Quadratic electro-optic effect due to the quantum-confined Stark effect in quantum wells,” Appl. Phys. Lett. 50, 842–844 (1987).
[CrossRef]

Weiss, C.

A. J. McHugh, M. Gouterman, and C. Weiss, “Porphyrins XXIV. Energy, oscillator strength, and Zeeman splitting calculations (SCMO-CI) for phthalocyanine, porphyrins and related ring systems,” Theor. Chim. Acta 24, 346–370 (1972).
[CrossRef]

Wong, K. Y.

J. W. Wu, J. R. Heflin, R. A. Norwood, K. Y. Wong, O. Zamani-Khamiri, A. F. Garito, P. Kalyanaraman, and J. Sounik, “Nonlinear-optical processes in low-dimensional conjugated structures,” J. Opt. Soc. Am. B 6, 707–720 (1989).
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[CrossRef]

Worland, R.

R. Worland, S. D. Phillips, W. C. Walker, and A. J. Heeger, “Electroabsorption and nonlinear optical constants of trans-polyacetylene and poly(3-hexylthiophene),” Synth. Met. 28, D663–D667 (1989).
[CrossRef]

Wu, J. W.

Wu, X.-L.

J. W. Perry, K. Mansour, I.-Y. S. Lee, X.-L. Wu, P. V. Bedworth, C.-T. Chen, D. Ng, S. R. Marder, P. Miles, T. Wada, M. Tian, and H. Sasabe, “Organic optical limiter with a strong nonlinear absorptive response,” Science 273, 1533–1536 (1996).
[CrossRef]

Yamada, A.

A. Terasaki, M. Hosoda, T. Wada, H. Tada, A. Koma, A. Yamada, H. Sasabe, A. F. Garito, and T. Kobayashi, “Femtosecond spectroscopy of vanadyl phthalocyanines in various molecular arrangements,” J. Phys. Chem. 96, 10534–10542 (1992).
[CrossRef]

M. Hosoda, T. Wada, A. Yamada, A. F. Garito, and H. Sasabe, “Phase and third-order optical nonlinearities in tetravalent metallophthalocyanine thin films,” Jpn. J. Appl. Phys. 30, L1486–L1488 (1991).
[CrossRef]

M. Hosoda, T. Wada, A. Yamada, A. F. Garito, and H. Sasabe, “Third-order nonlinear optical properties in soluble phthalocyanines with tert-butyl substituents,” Jpn. J. Appl. Phys. 30, 1715–1719 (1991).
[CrossRef]

T. Wada, Y. Matsuoka, K. Shigehara, A. Yamada, A. F. Garito, and H. Sasabe, “Organic nonlinear thin film: phthalocyanine derivatives,” in Photoresponsive Materials, M. Doyama, S. Somiya, R. P. H. Chang, and S. Tazuke, eds., Mater. Res. Soc. Symp. Proc. 12, 75–80 (1989).

Yamamoto, T.

M. Hosoda, T. Wada, T. Yamamoto, A. Kaneko, A. F. Garito, and H. Sasabe, “Enhancement of third-order optical nonlinearities of soluble vanadyl phthalocyanines in doped polymer films,” Jpn. J. Appl. Phys. 31, 1071–1075 (1992).
[CrossRef]

Yanagi, S.

S. Yanagi, T. Wada, J. Kumar, H. Sasabe, and K. Sasaki, “Electroabsorption spectra and nonlinear optical susceptibility of tetrakis tert-butyl phthalocyanine,” Mol. Cryst. Liq. Cryst. 255, 167–175 (1994).
[CrossRef]

Zamani-Khamiri, O.

J. W. Wu, J. R. Heflin, R. A. Norwood, K. Y. Wong, O. Zamani-Khamiri, A. F. Garito, P. Kalyanaraman, and J. Sounik, “Nonlinear-optical processes in low-dimensional conjugated structures,” J. Opt. Soc. Am. B 6, 707–720 (1989).
[CrossRef]

J. R. Heflin, K. Y. Wong, O. Zamani-Khamiri, and A. F. Garito, “Nonlinear optical properties of linear chains and electron-correlation effects,” Phys. Rev. B 38, 1573–1576 (1988).
[CrossRef]

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[CrossRef]

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[CrossRef]

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[CrossRef]

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[CrossRef]

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[CrossRef]

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[CrossRef]

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A. Terasaki, M. Hosoda, T. Wada, H. Tada, A. Koma, A. Yamada, H. Sasabe, A. F. Garito, and T. Kobayashi, “Femtosecond spectroscopy of vanadyl phthalocyanines in various molecular arrangements,” J. Phys. Chem. 96, 10534–10542 (1992).
[CrossRef]

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[CrossRef]

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M. Hosoda, T. Wada, A. Yamada, A. F. Garito, and H. Sasabe, “Phase and third-order optical nonlinearities in tetravalent metallophthalocyanine thin films,” Jpn. J. Appl. Phys. 30, L1486–L1488 (1991).
[CrossRef]

M. Hosoda, T. Wada, T. Yamamoto, A. Kaneko, A. F. Garito, and H. Sasabe, “Enhancement of third-order optical nonlinearities of soluble vanadyl phthalocyanines in doped polymer films,” Jpn. J. Appl. Phys. 31, 1071–1075 (1992).
[CrossRef]

M. Hosoda, T. Wada, A. Yamada, A. F. Garito, and H. Sasabe, “Third-order nonlinear optical properties in soluble phthalocyanines with tert-butyl substituents,” Jpn. J. Appl. Phys. 30, 1715–1719 (1991).
[CrossRef]

Mater. Res. Soc. Symp. Proc. (1)

T. Wada, Y. Matsuoka, K. Shigehara, A. Yamada, A. F. Garito, and H. Sasabe, “Organic nonlinear thin film: phthalocyanine derivatives,” in Photoresponsive Materials, M. Doyama, S. Somiya, R. P. H. Chang, and S. Tazuke, eds., Mater. Res. Soc. Symp. Proc. 12, 75–80 (1989).

Mol. Cryst. Liq. Cryst. (1)

S. Yanagi, T. Wada, J. Kumar, H. Sasabe, and K. Sasaki, “Electroabsorption spectra and nonlinear optical susceptibility of tetrakis tert-butyl phthalocyanine,” Mol. Cryst. Liq. Cryst. 255, 167–175 (1994).
[CrossRef]

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[CrossRef]

J. R. Heflin, K. Y. Wong, O. Zamani-Khamiri, and A. F. Garito, “Nonlinear optical properties of linear chains and electron-correlation effects,” Phys. Rev. B 38, 1573–1576 (1988).
[CrossRef]

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T. Wada and H. Sasabe, “Metallophthalocyanine: aggregation and nonlinear optics,” in Organic, Metallo-Organic, and Polymeric Materials for Nonlinear Optical Applications, S. R. Marder and J. W. Perry, eds., Proc. SPIE 2143, 164–171 (1994).
[CrossRef]

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[CrossRef]

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R. Worland, S. D. Phillips, W. C. Walker, and A. J. Heeger, “Electroabsorption and nonlinear optical constants of trans-polyacetylene and poly(3-hexylthiophene),” Synth. Met. 28, D663–D667 (1989).
[CrossRef]

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H. Kobayashi, K. Matsumoto, and T. Sonoda, “Active transport of alkali metal ions under two-phase conditions. Synthesis and application of highly lipophilic phthalocyanines with a large number of pendant polyfluoroalkoxyl groups,” in Proceedings of the 2nd International Symposium on the Chemistry of Functional Dyes (Mita, Osaka, Japan, 1992), pp. 290–295.

M. Tian, T. Wada, and H. Sasabe, “Synthesis of unsymmetrically substituted dodecakis(trifluoroethoxy)phthalo cyaninato vanadyl complexes,” J. Heterocyc. Chem. 34, 171–176 (1997).
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W. Eberhardt and M. Hanack, “Synthesis of hexadeca alkoxy-substituted nickel and iron phthalocyanines,” Synthesis 95–100 (1997).
[CrossRef]

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H. S. Nalwa and J. S. Shirk, “Nonlinear optical properties of metallophthalocyanines,” in Phthalocyanines, Properties and Applications, C. C. Leznoff and A. B. P. Lever, eds. (VCH, New York, 1996), Vol. 4, pp. 79–181, and references therein.

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Figures (9)

Fig. 1
Fig. 1

Molecular structures of nonaggregated metallophthalocyanines for nonlinear optics.

Fig. 2
Fig. 2

Reagents and conditions: i, potassium carbonate– N,N-dimethylformamide, room temperature, 12–24 h; ii, urea, 190–200 °C, 2 h; iii, H+–water, reflux, 2 h; iv, 1,5-diaza bicyclo[4,3,0]-5-nonene/ethanol, reflux, 45 h; v, H+water, reflux, 2 h.

Fig. 3
Fig. 3

UV–visible absorption spectra of VOPc(TFE)16 in solution and in doped PMMA films: a, neat film without polymer; b, doped concentration 10 wt. %; c, doped concentration 1 wt. %; d, doped concentration 0.1 wt. %; e, chloroform solution.

Fig. 4
Fig. 4

UV–visible absorption spectra of ZnPc(TFE)16 in solution and in doped PMMA films: i, neat film without polymer; ii, doped concentration 10 wt. %; iii, doped concentration 1 wt. %; iv, doped concentration 0.1 wt. %; v, chloroform solution.

Fig. 5
Fig. 5

UV–visible absorption spectra of VOPc(OEt)16 in solution and in doped PMMA films: I, neat film without polymer; II, doped concentration 10 wt. %; III, doped concentration 1 wt. %; IV, doped concentration 0.1 wt. %; V, chloroform solution.

Fig. 6
Fig. 6

Spectra of the real and the imaginary parts of third-order susceptibility χ(3)(-ω; ω, 0, 0) of VOPc(TFE)16 (doped in PMMA, 1 wt. %; film thickness 10 μm) upon a glass substrate.

Fig. 7
Fig. 7

Spectra of the real and the imaginary parts of third-order susceptibility χ(3)(-ω, ω, 0, 0) of VOPc(OEt)16 (doped in PMMA, 1 wt. %; film thickness 13.1 μm) upon a glass substrate.

Fig. 8
Fig. 8

Spectra of the real and the imaginary parts of third-order susceptibility χ(3)(-ω; ω, 0, 0) of VOPc(TFE)16 (doped in PMMA, 0.1 wt. %; film thickness 20 μm) upon a glass substrate.

Fig. 9
Fig. 9

Spectra of the real and the imaginary parts of third-order susceptibility χ(3)(-ω; ω, 0, 0) of ZnPc(TFE)16 (doped in PMMA, 0.1 wt. %; film thickness 12.3 μm) upon a glass substrate.

Equations (6)

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

Δα=-ΔI/Id,
n(ω)=1πP0 cα(ω)ω2-ω2 dω-1,
k(ω)=cα(ω)2ω,
Δn(ω)=1πPω1ω2 cΔα(ω)ω2-ω2 dω,
Δk(ω)=cΔα(ω)2ω.
χ(3)(-ω; ω, 0, 0)=NΔN2πF2,

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