Abstract

Waveguide photodegradation studies have been carried out to investigate the photostabilities of a series of nonlinear optical chromophores doped into poly(methyl methacrylate) waveguide films. The films were exposed to optical wavelengths lying either within these materials’ main absorption bands or in the near-infrared region. Degradation studies were carried out in air, vacuum, and nitrogen environments at room temperature. Experimental results indicate that the principal photodegradation mechanism in operation is photo-oxidation. A simple analytical model indicated the relative sensitivity to photo-oxidation of the materials studied.

© 2000 Optical Society of America

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    [CrossRef] [PubMed]
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1998 (4)

J. Kobayashi, T. Matsuura, S. Sasaki, T. Maruno, “Directional couplers using fluorinated polyimide waveguides,” J. Lightwave Technol. 16, 610–614 (1998).
[CrossRef]

A. Costela, I. Garcia-Moreno, J. Barraso, R. Sastre, “Laser performance of Coumarin 540A dye molecules in polymeric host media with different viscosities: from liquid solution to solid polymer matrix,” J. Appl. Phys. 83, 650–660 (1998).
[CrossRef]

T. Watanabe, M. Hikita, M. Amano, Y. Shuto, S. Tomaru, “Vertically stacked coupler and serially grafted waveguide: hybrid waveguide structures formed using an electro-optic polymer,” J. Appl. Phys. 83, 639–649 (1998).
[CrossRef]

Q. Zhang, M. Canva, G. Stegeman, “Wavelength dependence of 4-dimethylamino-4′-nitrostilbene polymer thin film photodegradation,” Appl. Phys. Lett. 73, 912–914 (1998).
[CrossRef]

1997 (3)

W.-Y. Hwang, M.-C. Oh, H.-M. Lee, H. Park, J.-J. Kim, “Polymeric 2 × 2 electrooptic switch consisting of asymmetric Y junctions and Mach–Zehnder interferometer,” IEEE Photon. Technol. Lett. 9, 761–763 (1997).
[CrossRef]

D. Chen, H. R. Fetterman, A. Chen, W. H. Steier, L. R. Dalton, W. Wang, Y. Shi, “Demonstration of 110 GHz electro-optic polymer modulators,” Appl. Phys. Lett. 70, 3335–3337 (1997).
[CrossRef]

M. Szablewski, P. R. Thomas, A. Thornton, D. Bloor, G. H. Cross, J. M. Cole, J. A. K. Howard, M. Malagoli, F. Meyers, J.-L. Brédas, W. Wenseleers, E. Goovaerts, “Highly dipolar, optically nonlinear adducts of tetracyano-p-quinodimethane: synthesis, physical characterization, and theoretical aspects,” J. Am. Chem. Soc. 119, 3144–3154 (1997).
[CrossRef]

1996 (5)

A. Dubois, M. Canva, A. Brun, F. Chaput, J.-P. Boilot, “Photostability of dye molecules trapped in solid matrices,” Appl. Opt. 35, 3193–3199 (1996).
[CrossRef] [PubMed]

A. Dubois, M. Canva, A. Brun, F. Chaput, J.-P. Boilot, “Enhanced photostability of dye molecules trapped in solid xerogel matrices,” Synth. Met. 81, 305–308 (1996).
[CrossRef]

M. Usui, M. Hikita, T. Watanabe, M. Amano, S. Sugawara, S. Hayashida, S. Imamura, “Low-loss passive polymer optical waveguides with high environmental stability,” J. Lightwave Technol. 14, 2338–2343 (1996).
[CrossRef]

Th. Knoche, L. Müller, R. Klein, A. Neyer, “Low loss polymer waveguides at 1300 and 1500 nm using halogenated acrylates,” Electron. Lett. 32, 1284–1285 (1996).
[CrossRef]

J. Vydra, H. Beisinghoff, T. Tschudi, M. Eich, “Photodecay mechanisms in side chain nonlinear optical polymethacrylates,” Appl. Phys. Lett. 69, 1035–1037 (1996).
[CrossRef]

1995 (5)

J. Ma, S. Lin, W. Feng, R. J. Feuerstein, B. Hooker, A. R. Mickelson, “Modeling photobleached optical polymer waveguides,” Appl. Opt. 34, 5352–5360 (1995).
[CrossRef] [PubMed]

T. Zyung, J.-J. Kim, “Photodegradation of poly(p-phenylenevinylene) by laser light at the peak wavelength of electroluminescence,” Appl. Phys. Lett. 67, 3420–3422 (1995).
[CrossRef]

C. F. Kane, R. R. Krchnavek, “Processing and characterization of benzocyclobutene optical waveguides,” IEEE Trans. Components Packag. Manuf. Technol. Part B 18, 565–571 (1995).
[CrossRef]

R. Sastre, A. Costela, “Polymeric solid-state dye lasers,” Adv. Mater. 7, 198–202 (1995).
[CrossRef]

J. C. Cole, J. A. K. Howard, G. H. Cross, M. Szablewski, (Z)-{4-[1-cyano-3-(diethyliminio)-1-propenyl]phenyl}-dicyanomethanide, a novel ‘blue window’ zwitterionic molecule for nonlinear optics,” Acta Crystallogr. C 51, 715–718 (1995).

1994 (2)

M. Szablewski, “Novel reactions of TCNQ: formation of zwitterions for nonlinear optics by reaction with examines,” J. Org. Chem. 59, 954–956 (1994).
[CrossRef]

J.-J. Kim, T. Zyung, W.-Y. Hwang, “Photochemically formed refractive index profiles in nonlinear optical polymer thin films,” Appl. Phys. Lett. 64, 3488–3490 (1994).
[CrossRef]

1993 (3)

M. A. Mortazavi, H. N. Yoon, C. C. Teng, “Optical power handling properties of polymeric nonlinear optical waveguides,” J. Appl. Phys. 74, 4871–4876 (1993).
[CrossRef]

R. A. Norwood, D. R. Holcomb, F. F. So, “Polymers for nonlinear optics: absorption, two-photon absorption and photodegradation,” Nonlin. Opt. 6, 193–204 (1993).

M. Dumont, Z. Sekkat, R. Loucif-Saibi, K. Nakatini, J. A. Delaire, “Photoisomerization, photoinduced orientation and orientational relaxation in polymeric films,” Nonlin. Opt. 5, 395–406 (1993).

1992 (1)

1991 (1)

1989 (1)

B. L. Booth, “Low loss channel waveguides in polymers,” J. Lightwave Technol. 7, 1445–1453 (1989).
[CrossRef]

1972 (1)

1971 (1)

Amano, M.

T. Watanabe, M. Hikita, M. Amano, Y. Shuto, S. Tomaru, “Vertically stacked coupler and serially grafted waveguide: hybrid waveguide structures formed using an electro-optic polymer,” J. Appl. Phys. 83, 639–649 (1998).
[CrossRef]

M. Usui, M. Hikita, T. Watanabe, M. Amano, S. Sugawara, S. Hayashida, S. Imamura, “Low-loss passive polymer optical waveguides with high environmental stability,” J. Lightwave Technol. 14, 2338–2343 (1996).
[CrossRef]

Barraso, J.

A. Costela, I. Garcia-Moreno, J. Barraso, R. Sastre, “Laser performance of Coumarin 540A dye molecules in polymeric host media with different viscosities: from liquid solution to solid polymer matrix,” J. Appl. Phys. 83, 650–660 (1998).
[CrossRef]

Basster, G. C.

R. M. Siverstein, G. C. Basster, T. C. Morrill, Spectrometric Identification of Organic Compounds (Wiley, New York, 1981).

Beisinghoff, H.

J. Vydra, H. Beisinghoff, T. Tschudi, M. Eich, “Photodecay mechanisms in side chain nonlinear optical polymethacrylates,” Appl. Phys. Lett. 69, 1035–1037 (1996).
[CrossRef]

Bloor, D.

M. Szablewski, P. R. Thomas, A. Thornton, D. Bloor, G. H. Cross, J. M. Cole, J. A. K. Howard, M. Malagoli, F. Meyers, J.-L. Brédas, W. Wenseleers, E. Goovaerts, “Highly dipolar, optically nonlinear adducts of tetracyano-p-quinodimethane: synthesis, physical characterization, and theoretical aspects,” J. Am. Chem. Soc. 119, 3144–3154 (1997).
[CrossRef]

Boilot, J.-P.

A. Dubois, M. Canva, A. Brun, F. Chaput, J.-P. Boilot, “Photostability of dye molecules trapped in solid matrices,” Appl. Opt. 35, 3193–3199 (1996).
[CrossRef] [PubMed]

A. Dubois, M. Canva, A. Brun, F. Chaput, J.-P. Boilot, “Enhanced photostability of dye molecules trapped in solid xerogel matrices,” Synth. Met. 81, 305–308 (1996).
[CrossRef]

Booth, B. L.

B. L. Booth, “Low loss channel waveguides in polymers,” J. Lightwave Technol. 7, 1445–1453 (1989).
[CrossRef]

Bosshard, C.

C. Bosshard, K. Sutter, Ph. Prêtre, J. Hulliger, M. Flörsheimer, P. Kaatz, P. Günter, Organic Nonlinear Optical Materials, Vol. 1 of Advances in Nonlinear Optics (Gordon & Breach, Amsterdam, 1995), p 181.

Brédas, J.-L.

M. Szablewski, P. R. Thomas, A. Thornton, D. Bloor, G. H. Cross, J. M. Cole, J. A. K. Howard, M. Malagoli, F. Meyers, J.-L. Brédas, W. Wenseleers, E. Goovaerts, “Highly dipolar, optically nonlinear adducts of tetracyano-p-quinodimethane: synthesis, physical characterization, and theoretical aspects,” J. Am. Chem. Soc. 119, 3144–3154 (1997).
[CrossRef]

Brun, A.

A. Dubois, M. Canva, A. Brun, F. Chaput, J.-P. Boilot, “Enhanced photostability of dye molecules trapped in solid xerogel matrices,” Synth. Met. 81, 305–308 (1996).
[CrossRef]

A. Dubois, M. Canva, A. Brun, F. Chaput, J.-P. Boilot, “Photostability of dye molecules trapped in solid matrices,” Appl. Opt. 35, 3193–3199 (1996).
[CrossRef] [PubMed]

Canva, M.

Q. Zhang, M. Canva, G. Stegeman, “Wavelength dependence of 4-dimethylamino-4′-nitrostilbene polymer thin film photodegradation,” Appl. Phys. Lett. 73, 912–914 (1998).
[CrossRef]

A. Dubois, M. Canva, A. Brun, F. Chaput, J.-P. Boilot, “Photostability of dye molecules trapped in solid matrices,” Appl. Opt. 35, 3193–3199 (1996).
[CrossRef] [PubMed]

A. Dubois, M. Canva, A. Brun, F. Chaput, J.-P. Boilot, “Enhanced photostability of dye molecules trapped in solid xerogel matrices,” Synth. Met. 81, 305–308 (1996).
[CrossRef]

Capolla, N.

Chaput, F.

A. Dubois, M. Canva, A. Brun, F. Chaput, J.-P. Boilot, “Photostability of dye molecules trapped in solid matrices,” Appl. Opt. 35, 3193–3199 (1996).
[CrossRef] [PubMed]

A. Dubois, M. Canva, A. Brun, F. Chaput, J.-P. Boilot, “Enhanced photostability of dye molecules trapped in solid xerogel matrices,” Synth. Met. 81, 305–308 (1996).
[CrossRef]

Chemla, D. S.

D. S. Chemla, J. Zyss, Nonlinear Optical Properties of Organic Molecules and Crystals (Academic, London, 1986), Vol. 1.

Chen, A.

D. Chen, H. R. Fetterman, A. Chen, W. H. Steier, L. R. Dalton, W. Wang, Y. Shi, “Demonstration of 110 GHz electro-optic polymer modulators,” Appl. Phys. Lett. 70, 3335–3337 (1997).
[CrossRef]

Chen, D.

D. Chen, H. R. Fetterman, A. Chen, W. H. Steier, L. R. Dalton, W. Wang, Y. Shi, “Demonstration of 110 GHz electro-optic polymer modulators,” Appl. Phys. Lett. 70, 3335–3337 (1997).
[CrossRef]

Clough, R. L.

P. R. Ogilby, M. Kristiansen, D. O. Martine, R. D. Scurlock, V. L. Taylor, R. L. Clough, “Formation and removal of singlet (a′Δg) oxygen in bulk polymers: events that may influence photodegradation,” in Polymer Durability: Degradation, Durability and Lifetime Prediction, R. L. Clough, N. C. Billingham, K. T. Gillen, eds. (American Chemical Society, Washington, D.C., 1996), pp. 113–126.

Cole, J. C.

J. C. Cole, J. A. K. Howard, G. H. Cross, M. Szablewski, (Z)-{4-[1-cyano-3-(diethyliminio)-1-propenyl]phenyl}-dicyanomethanide, a novel ‘blue window’ zwitterionic molecule for nonlinear optics,” Acta Crystallogr. C 51, 715–718 (1995).

Cole, J. M.

M. Szablewski, P. R. Thomas, A. Thornton, D. Bloor, G. H. Cross, J. M. Cole, J. A. K. Howard, M. Malagoli, F. Meyers, J.-L. Brédas, W. Wenseleers, E. Goovaerts, “Highly dipolar, optically nonlinear adducts of tetracyano-p-quinodimethane: synthesis, physical characterization, and theoretical aspects,” J. Am. Chem. Soc. 119, 3144–3154 (1997).
[CrossRef]

Costela, A.

A. Costela, I. Garcia-Moreno, J. Barraso, R. Sastre, “Laser performance of Coumarin 540A dye molecules in polymeric host media with different viscosities: from liquid solution to solid polymer matrix,” J. Appl. Phys. 83, 650–660 (1998).
[CrossRef]

R. Sastre, A. Costela, “Polymeric solid-state dye lasers,” Adv. Mater. 7, 198–202 (1995).
[CrossRef]

Cross, G. H.

M. Szablewski, P. R. Thomas, A. Thornton, D. Bloor, G. H. Cross, J. M. Cole, J. A. K. Howard, M. Malagoli, F. Meyers, J.-L. Brédas, W. Wenseleers, E. Goovaerts, “Highly dipolar, optically nonlinear adducts of tetracyano-p-quinodimethane: synthesis, physical characterization, and theoretical aspects,” J. Am. Chem. Soc. 119, 3144–3154 (1997).
[CrossRef]

J. C. Cole, J. A. K. Howard, G. H. Cross, M. Szablewski, (Z)-{4-[1-cyano-3-(diethyliminio)-1-propenyl]phenyl}-dicyanomethanide, a novel ‘blue window’ zwitterionic molecule for nonlinear optics,” Acta Crystallogr. C 51, 715–718 (1995).

Dalton, L. R.

D. Chen, H. R. Fetterman, A. Chen, W. H. Steier, L. R. Dalton, W. Wang, Y. Shi, “Demonstration of 110 GHz electro-optic polymer modulators,” Appl. Phys. Lett. 70, 3335–3337 (1997).
[CrossRef]

Delaire, J. A.

M. Dumont, Z. Sekkat, R. Loucif-Saibi, K. Nakatini, J. A. Delaire, “Photoisomerization, photoinduced orientation and orientational relaxation in polymeric films,” Nonlin. Opt. 5, 395–406 (1993).

Dubois, A.

A. Dubois, M. Canva, A. Brun, F. Chaput, J.-P. Boilot, “Enhanced photostability of dye molecules trapped in solid xerogel matrices,” Synth. Met. 81, 305–308 (1996).
[CrossRef]

A. Dubois, M. Canva, A. Brun, F. Chaput, J.-P. Boilot, “Photostability of dye molecules trapped in solid matrices,” Appl. Opt. 35, 3193–3199 (1996).
[CrossRef] [PubMed]

Dumont, M.

M. Dumont, Z. Sekkat, R. Loucif-Saibi, K. Nakatini, J. A. Delaire, “Photoisomerization, photoinduced orientation and orientational relaxation in polymeric films,” Nonlin. Opt. 5, 395–406 (1993).

Dyumaev, K. M.

Eich, M.

J. Vydra, H. Beisinghoff, T. Tschudi, M. Eich, “Photodecay mechanisms in side chain nonlinear optical polymethacrylates,” Appl. Phys. Lett. 69, 1035–1037 (1996).
[CrossRef]

Feng, W.

Fetterman, H. R.

D. Chen, H. R. Fetterman, A. Chen, W. H. Steier, L. R. Dalton, W. Wang, Y. Shi, “Demonstration of 110 GHz electro-optic polymer modulators,” Appl. Phys. Lett. 70, 3335–3337 (1997).
[CrossRef]

Feuerstein, R. J.

Flörsheimer, M.

C. Bosshard, K. Sutter, Ph. Prêtre, J. Hulliger, M. Flörsheimer, P. Kaatz, P. Günter, Organic Nonlinear Optical Materials, Vol. 1 of Advances in Nonlinear Optics (Gordon & Breach, Amsterdam, 1995), p 181.

Garcia-Moreno, I.

A. Costela, I. Garcia-Moreno, J. Barraso, R. Sastre, “Laser performance of Coumarin 540A dye molecules in polymeric host media with different viscosities: from liquid solution to solid polymer matrix,” J. Appl. Phys. 83, 650–660 (1998).
[CrossRef]

Goovaerts, E.

M. Szablewski, P. R. Thomas, A. Thornton, D. Bloor, G. H. Cross, J. M. Cole, J. A. K. Howard, M. Malagoli, F. Meyers, J.-L. Brédas, W. Wenseleers, E. Goovaerts, “Highly dipolar, optically nonlinear adducts of tetracyano-p-quinodimethane: synthesis, physical characterization, and theoretical aspects,” J. Am. Chem. Soc. 119, 3144–3154 (1997).
[CrossRef]

Günter, P.

C. Bosshard, K. Sutter, Ph. Prêtre, J. Hulliger, M. Flörsheimer, P. Kaatz, P. Günter, Organic Nonlinear Optical Materials, Vol. 1 of Advances in Nonlinear Optics (Gordon & Breach, Amsterdam, 1995), p 181.

Hayashida, S.

M. Usui, M. Hikita, T. Watanabe, M. Amano, S. Sugawara, S. Hayashida, S. Imamura, “Low-loss passive polymer optical waveguides with high environmental stability,” J. Lightwave Technol. 14, 2338–2343 (1996).
[CrossRef]

Hikita, M.

T. Watanabe, M. Hikita, M. Amano, Y. Shuto, S. Tomaru, “Vertically stacked coupler and serially grafted waveguide: hybrid waveguide structures formed using an electro-optic polymer,” J. Appl. Phys. 83, 639–649 (1998).
[CrossRef]

M. Usui, M. Hikita, T. Watanabe, M. Amano, S. Sugawara, S. Hayashida, S. Imamura, “Low-loss passive polymer optical waveguides with high environmental stability,” J. Lightwave Technol. 14, 2338–2343 (1996).
[CrossRef]

Holcomb, D. R.

R. A. Norwood, D. R. Holcomb, F. F. So, “Polymers for nonlinear optics: absorption, two-photon absorption and photodegradation,” Nonlin. Opt. 6, 193–204 (1993).

Hooker, B.

Hornak, L. A.

L. A. Hornak, Polymers for lightwave and integrated optics (Marcel Dekker, New York, 1992), Chaps. 1 and 2.

Howard, J. A. K.

M. Szablewski, P. R. Thomas, A. Thornton, D. Bloor, G. H. Cross, J. M. Cole, J. A. K. Howard, M. Malagoli, F. Meyers, J.-L. Brédas, W. Wenseleers, E. Goovaerts, “Highly dipolar, optically nonlinear adducts of tetracyano-p-quinodimethane: synthesis, physical characterization, and theoretical aspects,” J. Am. Chem. Soc. 119, 3144–3154 (1997).
[CrossRef]

J. C. Cole, J. A. K. Howard, G. H. Cross, M. Szablewski, (Z)-{4-[1-cyano-3-(diethyliminio)-1-propenyl]phenyl}-dicyanomethanide, a novel ‘blue window’ zwitterionic molecule for nonlinear optics,” Acta Crystallogr. C 51, 715–718 (1995).

Hulliger, J.

C. Bosshard, K. Sutter, Ph. Prêtre, J. Hulliger, M. Flörsheimer, P. Kaatz, P. Günter, Organic Nonlinear Optical Materials, Vol. 1 of Advances in Nonlinear Optics (Gordon & Breach, Amsterdam, 1995), p 181.

Hwang, W.-Y.

W.-Y. Hwang, M.-C. Oh, H.-M. Lee, H. Park, J.-J. Kim, “Polymeric 2 × 2 electrooptic switch consisting of asymmetric Y junctions and Mach–Zehnder interferometer,” IEEE Photon. Technol. Lett. 9, 761–763 (1997).
[CrossRef]

J.-J. Kim, T. Zyung, W.-Y. Hwang, “Photochemically formed refractive index profiles in nonlinear optical polymer thin films,” Appl. Phys. Lett. 64, 3488–3490 (1994).
[CrossRef]

Imamura, S.

M. Usui, M. Hikita, T. Watanabe, M. Amano, S. Sugawara, S. Hayashida, S. Imamura, “Low-loss passive polymer optical waveguides with high environmental stability,” J. Lightwave Technol. 14, 2338–2343 (1996).
[CrossRef]

Kaatz, P.

C. Bosshard, K. Sutter, Ph. Prêtre, J. Hulliger, M. Flörsheimer, P. Kaatz, P. Günter, Organic Nonlinear Optical Materials, Vol. 1 of Advances in Nonlinear Optics (Gordon & Breach, Amsterdam, 1995), p 181.

Kane, C. F.

C. F. Kane, R. R. Krchnavek, “Processing and characterization of benzocyclobutene optical waveguides,” IEEE Trans. Components Packag. Manuf. Technol. Part B 18, 565–571 (1995).
[CrossRef]

Kim, J.-J.

W.-Y. Hwang, M.-C. Oh, H.-M. Lee, H. Park, J.-J. Kim, “Polymeric 2 × 2 electrooptic switch consisting of asymmetric Y junctions and Mach–Zehnder interferometer,” IEEE Photon. Technol. Lett. 9, 761–763 (1997).
[CrossRef]

T. Zyung, J.-J. Kim, “Photodegradation of poly(p-phenylenevinylene) by laser light at the peak wavelength of electroluminescence,” Appl. Phys. Lett. 67, 3420–3422 (1995).
[CrossRef]

J.-J. Kim, T. Zyung, W.-Y. Hwang, “Photochemically formed refractive index profiles in nonlinear optical polymer thin films,” Appl. Phys. Lett. 64, 3488–3490 (1994).
[CrossRef]

Klein, R.

Th. Knoche, L. Müller, R. Klein, A. Neyer, “Low loss polymer waveguides at 1300 and 1500 nm using halogenated acrylates,” Electron. Lett. 32, 1284–1285 (1996).
[CrossRef]

Knoche, Th.

Th. Knoche, L. Müller, R. Klein, A. Neyer, “Low loss polymer waveguides at 1300 and 1500 nm using halogenated acrylates,” Electron. Lett. 32, 1284–1285 (1996).
[CrossRef]

Kobayashi, J.

Krchnavek, R. R.

C. F. Kane, R. R. Krchnavek, “Processing and characterization of benzocyclobutene optical waveguides,” IEEE Trans. Components Packag. Manuf. Technol. Part B 18, 565–571 (1995).
[CrossRef]

Kristiansen, M.

P. R. Ogilby, M. Kristiansen, D. O. Martine, R. D. Scurlock, V. L. Taylor, R. L. Clough, “Formation and removal of singlet (a′Δg) oxygen in bulk polymers: events that may influence photodegradation,” in Polymer Durability: Degradation, Durability and Lifetime Prediction, R. L. Clough, N. C. Billingham, K. T. Gillen, eds. (American Chemical Society, Washington, D.C., 1996), pp. 113–126.

Lee, H.-M.

W.-Y. Hwang, M.-C. Oh, H.-M. Lee, H. Park, J.-J. Kim, “Polymeric 2 × 2 electrooptic switch consisting of asymmetric Y junctions and Mach–Zehnder interferometer,” IEEE Photon. Technol. Lett. 9, 761–763 (1997).
[CrossRef]

Lessard, R. A.

Lin, S.

Loucif-Saibi, R.

M. Dumont, Z. Sekkat, R. Loucif-Saibi, K. Nakatini, J. A. Delaire, “Photoisomerization, photoinduced orientation and orientational relaxation in polymeric films,” Nonlin. Opt. 5, 395–406 (1993).

Ma, J.

Malagoli, M.

M. Szablewski, P. R. Thomas, A. Thornton, D. Bloor, G. H. Cross, J. M. Cole, J. A. K. Howard, M. Malagoli, F. Meyers, J.-L. Brédas, W. Wenseleers, E. Goovaerts, “Highly dipolar, optically nonlinear adducts of tetracyano-p-quinodimethane: synthesis, physical characterization, and theoretical aspects,” J. Am. Chem. Soc. 119, 3144–3154 (1997).
[CrossRef]

Manenkov, A. A.

Martin, R. J.

Martine, D. O.

P. R. Ogilby, M. Kristiansen, D. O. Martine, R. D. Scurlock, V. L. Taylor, R. L. Clough, “Formation and removal of singlet (a′Δg) oxygen in bulk polymers: events that may influence photodegradation,” in Polymer Durability: Degradation, Durability and Lifetime Prediction, R. L. Clough, N. C. Billingham, K. T. Gillen, eds. (American Chemical Society, Washington, D.C., 1996), pp. 113–126.

Maruno, T.

Maslyukov, A. P.

Matsuura, T.

Matyushin, G. A.

Meyers, F.

M. Szablewski, P. R. Thomas, A. Thornton, D. Bloor, G. H. Cross, J. M. Cole, J. A. K. Howard, M. Malagoli, F. Meyers, J.-L. Brédas, W. Wenseleers, E. Goovaerts, “Highly dipolar, optically nonlinear adducts of tetracyano-p-quinodimethane: synthesis, physical characterization, and theoretical aspects,” J. Am. Chem. Soc. 119, 3144–3154 (1997).
[CrossRef]

Mickelson, A. R.

Morrill, T. C.

R. M. Siverstein, G. C. Basster, T. C. Morrill, Spectrometric Identification of Organic Compounds (Wiley, New York, 1981).

Mortazavi, M. A.

M. A. Mortazavi, H. N. Yoon, C. C. Teng, “Optical power handling properties of polymeric nonlinear optical waveguides,” J. Appl. Phys. 74, 4871–4876 (1993).
[CrossRef]

Müller, L.

Th. Knoche, L. Müller, R. Klein, A. Neyer, “Low loss polymer waveguides at 1300 and 1500 nm using halogenated acrylates,” Electron. Lett. 32, 1284–1285 (1996).
[CrossRef]

Nakatini, K.

M. Dumont, Z. Sekkat, R. Loucif-Saibi, K. Nakatini, J. A. Delaire, “Photoisomerization, photoinduced orientation and orientational relaxation in polymeric films,” Nonlin. Opt. 5, 395–406 (1993).

Nechitailo, V. S.

Neyer, A.

Th. Knoche, L. Müller, R. Klein, A. Neyer, “Low loss polymer waveguides at 1300 and 1500 nm using halogenated acrylates,” Electron. Lett. 32, 1284–1285 (1996).
[CrossRef]

Norwood, R. A.

R. A. Norwood, D. R. Holcomb, F. F. So, “Polymers for nonlinear optics: absorption, two-photon absorption and photodegradation,” Nonlin. Opt. 6, 193–204 (1993).

Ogilby, P. R.

P. R. Ogilby, M. Kristiansen, D. O. Martine, R. D. Scurlock, V. L. Taylor, R. L. Clough, “Formation and removal of singlet (a′Δg) oxygen in bulk polymers: events that may influence photodegradation,” in Polymer Durability: Degradation, Durability and Lifetime Prediction, R. L. Clough, N. C. Billingham, K. T. Gillen, eds. (American Chemical Society, Washington, D.C., 1996), pp. 113–126.

Oh, M.-C.

W.-Y. Hwang, M.-C. Oh, H.-M. Lee, H. Park, J.-J. Kim, “Polymeric 2 × 2 electrooptic switch consisting of asymmetric Y junctions and Mach–Zehnder interferometer,” IEEE Photon. Technol. Lett. 9, 761–763 (1997).
[CrossRef]

Park, H.

W.-Y. Hwang, M.-C. Oh, H.-M. Lee, H. Park, J.-J. Kim, “Polymeric 2 × 2 electrooptic switch consisting of asymmetric Y junctions and Mach–Zehnder interferometer,” IEEE Photon. Technol. Lett. 9, 761–763 (1997).
[CrossRef]

Prêtre, Ph.

C. Bosshard, K. Sutter, Ph. Prêtre, J. Hulliger, M. Flörsheimer, P. Kaatz, P. Günter, Organic Nonlinear Optical Materials, Vol. 1 of Advances in Nonlinear Optics (Gordon & Breach, Amsterdam, 1995), p 181.

Prokhorov, A. M.

Sasaki, S.

Sastre, R.

A. Costela, I. Garcia-Moreno, J. Barraso, R. Sastre, “Laser performance of Coumarin 540A dye molecules in polymeric host media with different viscosities: from liquid solution to solid polymer matrix,” J. Appl. Phys. 83, 650–660 (1998).
[CrossRef]

R. Sastre, A. Costela, “Polymeric solid-state dye lasers,” Adv. Mater. 7, 198–202 (1995).
[CrossRef]

Scurlock, R. D.

P. R. Ogilby, M. Kristiansen, D. O. Martine, R. D. Scurlock, V. L. Taylor, R. L. Clough, “Formation and removal of singlet (a′Δg) oxygen in bulk polymers: events that may influence photodegradation,” in Polymer Durability: Degradation, Durability and Lifetime Prediction, R. L. Clough, N. C. Billingham, K. T. Gillen, eds. (American Chemical Society, Washington, D.C., 1996), pp. 113–126.

Sekkat, Z.

M. Dumont, Z. Sekkat, R. Loucif-Saibi, K. Nakatini, J. A. Delaire, “Photoisomerization, photoinduced orientation and orientational relaxation in polymeric films,” Nonlin. Opt. 5, 395–406 (1993).

Shi, Y.

D. Chen, H. R. Fetterman, A. Chen, W. H. Steier, L. R. Dalton, W. Wang, Y. Shi, “Demonstration of 110 GHz electro-optic polymer modulators,” Appl. Phys. Lett. 70, 3335–3337 (1997).
[CrossRef]

Shuto, Y.

T. Watanabe, M. Hikita, M. Amano, Y. Shuto, S. Tomaru, “Vertically stacked coupler and serially grafted waveguide: hybrid waveguide structures formed using an electro-optic polymer,” J. Appl. Phys. 83, 639–649 (1998).
[CrossRef]

Siverstein, R. M.

R. M. Siverstein, G. C. Basster, T. C. Morrill, Spectrometric Identification of Organic Compounds (Wiley, New York, 1981).

Smolinsky, G.

So, F. F.

R. A. Norwood, D. R. Holcomb, F. F. So, “Polymers for nonlinear optics: absorption, two-photon absorption and photodegradation,” Nonlin. Opt. 6, 193–204 (1993).

Stegeman, G.

Q. Zhang, M. Canva, G. Stegeman, “Wavelength dependence of 4-dimethylamino-4′-nitrostilbene polymer thin film photodegradation,” Appl. Phys. Lett. 73, 912–914 (1998).
[CrossRef]

Steier, W. H.

D. Chen, H. R. Fetterman, A. Chen, W. H. Steier, L. R. Dalton, W. Wang, Y. Shi, “Demonstration of 110 GHz electro-optic polymer modulators,” Appl. Phys. Lett. 70, 3335–3337 (1997).
[CrossRef]

Sugawara, S.

M. Usui, M. Hikita, T. Watanabe, M. Amano, S. Sugawara, S. Hayashida, S. Imamura, “Low-loss passive polymer optical waveguides with high environmental stability,” J. Lightwave Technol. 14, 2338–2343 (1996).
[CrossRef]

Sutter, K.

C. Bosshard, K. Sutter, Ph. Prêtre, J. Hulliger, M. Flörsheimer, P. Kaatz, P. Günter, Organic Nonlinear Optical Materials, Vol. 1 of Advances in Nonlinear Optics (Gordon & Breach, Amsterdam, 1995), p 181.

Szablewski, M.

M. Szablewski, P. R. Thomas, A. Thornton, D. Bloor, G. H. Cross, J. M. Cole, J. A. K. Howard, M. Malagoli, F. Meyers, J.-L. Brédas, W. Wenseleers, E. Goovaerts, “Highly dipolar, optically nonlinear adducts of tetracyano-p-quinodimethane: synthesis, physical characterization, and theoretical aspects,” J. Am. Chem. Soc. 119, 3144–3154 (1997).
[CrossRef]

J. C. Cole, J. A. K. Howard, G. H. Cross, M. Szablewski, (Z)-{4-[1-cyano-3-(diethyliminio)-1-propenyl]phenyl}-dicyanomethanide, a novel ‘blue window’ zwitterionic molecule for nonlinear optics,” Acta Crystallogr. C 51, 715–718 (1995).

M. Szablewski, “Novel reactions of TCNQ: formation of zwitterions for nonlinear optics by reaction with examines,” J. Org. Chem. 59, 954–956 (1994).
[CrossRef]

Taylor, V. L.

P. R. Ogilby, M. Kristiansen, D. O. Martine, R. D. Scurlock, V. L. Taylor, R. L. Clough, “Formation and removal of singlet (a′Δg) oxygen in bulk polymers: events that may influence photodegradation,” in Polymer Durability: Degradation, Durability and Lifetime Prediction, R. L. Clough, N. C. Billingham, K. T. Gillen, eds. (American Chemical Society, Washington, D.C., 1996), pp. 113–126.

Teng, C. C.

M. A. Mortazavi, H. N. Yoon, C. C. Teng, “Optical power handling properties of polymeric nonlinear optical waveguides,” J. Appl. Phys. 74, 4871–4876 (1993).
[CrossRef]

Thomas, P. R.

M. Szablewski, P. R. Thomas, A. Thornton, D. Bloor, G. H. Cross, J. M. Cole, J. A. K. Howard, M. Malagoli, F. Meyers, J.-L. Brédas, W. Wenseleers, E. Goovaerts, “Highly dipolar, optically nonlinear adducts of tetracyano-p-quinodimethane: synthesis, physical characterization, and theoretical aspects,” J. Am. Chem. Soc. 119, 3144–3154 (1997).
[CrossRef]

Thornton, A.

M. Szablewski, P. R. Thomas, A. Thornton, D. Bloor, G. H. Cross, J. M. Cole, J. A. K. Howard, M. Malagoli, F. Meyers, J.-L. Brédas, W. Wenseleers, E. Goovaerts, “Highly dipolar, optically nonlinear adducts of tetracyano-p-quinodimethane: synthesis, physical characterization, and theoretical aspects,” J. Am. Chem. Soc. 119, 3144–3154 (1997).
[CrossRef]

Tien, P. K.

Tomaru, S.

T. Watanabe, M. Hikita, M. Amano, Y. Shuto, S. Tomaru, “Vertically stacked coupler and serially grafted waveguide: hybrid waveguide structures formed using an electro-optic polymer,” J. Appl. Phys. 83, 639–649 (1998).
[CrossRef]

Tschudi, T.

J. Vydra, H. Beisinghoff, T. Tschudi, M. Eich, “Photodecay mechanisms in side chain nonlinear optical polymethacrylates,” Appl. Phys. Lett. 69, 1035–1037 (1996).
[CrossRef]

Usui, M.

M. Usui, M. Hikita, T. Watanabe, M. Amano, S. Sugawara, S. Hayashida, S. Imamura, “Low-loss passive polymer optical waveguides with high environmental stability,” J. Lightwave Technol. 14, 2338–2343 (1996).
[CrossRef]

Vydra, J.

J. Vydra, H. Beisinghoff, T. Tschudi, M. Eich, “Photodecay mechanisms in side chain nonlinear optical polymethacrylates,” Appl. Phys. Lett. 69, 1035–1037 (1996).
[CrossRef]

Wang, W.

D. Chen, H. R. Fetterman, A. Chen, W. H. Steier, L. R. Dalton, W. Wang, Y. Shi, “Demonstration of 110 GHz electro-optic polymer modulators,” Appl. Phys. Lett. 70, 3335–3337 (1997).
[CrossRef]

Watanabe, T.

T. Watanabe, M. Hikita, M. Amano, Y. Shuto, S. Tomaru, “Vertically stacked coupler and serially grafted waveguide: hybrid waveguide structures formed using an electro-optic polymer,” J. Appl. Phys. 83, 639–649 (1998).
[CrossRef]

M. Usui, M. Hikita, T. Watanabe, M. Amano, S. Sugawara, S. Hayashida, S. Imamura, “Low-loss passive polymer optical waveguides with high environmental stability,” J. Lightwave Technol. 14, 2338–2343 (1996).
[CrossRef]

Wenseleers, W.

M. Szablewski, P. R. Thomas, A. Thornton, D. Bloor, G. H. Cross, J. M. Cole, J. A. K. Howard, M. Malagoli, F. Meyers, J.-L. Brédas, W. Wenseleers, E. Goovaerts, “Highly dipolar, optically nonlinear adducts of tetracyano-p-quinodimethane: synthesis, physical characterization, and theoretical aspects,” J. Am. Chem. Soc. 119, 3144–3154 (1997).
[CrossRef]

Yoon, H. N.

M. A. Mortazavi, H. N. Yoon, C. C. Teng, “Optical power handling properties of polymeric nonlinear optical waveguides,” J. Appl. Phys. 74, 4871–4876 (1993).
[CrossRef]

Zhang, Q.

Q. Zhang, M. Canva, G. Stegeman, “Wavelength dependence of 4-dimethylamino-4′-nitrostilbene polymer thin film photodegradation,” Appl. Phys. Lett. 73, 912–914 (1998).
[CrossRef]

Zyss, J.

D. S. Chemla, J. Zyss, Nonlinear Optical Properties of Organic Molecules and Crystals (Academic, London, 1986), Vol. 1.

Zyung, T.

T. Zyung, J.-J. Kim, “Photodegradation of poly(p-phenylenevinylene) by laser light at the peak wavelength of electroluminescence,” Appl. Phys. Lett. 67, 3420–3422 (1995).
[CrossRef]

J.-J. Kim, T. Zyung, W.-Y. Hwang, “Photochemically formed refractive index profiles in nonlinear optical polymer thin films,” Appl. Phys. Lett. 64, 3488–3490 (1994).
[CrossRef]

Acta Crystallogr. C (1)

J. C. Cole, J. A. K. Howard, G. H. Cross, M. Szablewski, (Z)-{4-[1-cyano-3-(diethyliminio)-1-propenyl]phenyl}-dicyanomethanide, a novel ‘blue window’ zwitterionic molecule for nonlinear optics,” Acta Crystallogr. C 51, 715–718 (1995).

Adv. Mater. (1)

R. Sastre, A. Costela, “Polymeric solid-state dye lasers,” Adv. Mater. 7, 198–202 (1995).
[CrossRef]

Appl. Opt. (5)

Appl. Phys. Lett. (5)

T. Zyung, J.-J. Kim, “Photodegradation of poly(p-phenylenevinylene) by laser light at the peak wavelength of electroluminescence,” Appl. Phys. Lett. 67, 3420–3422 (1995).
[CrossRef]

D. Chen, H. R. Fetterman, A. Chen, W. H. Steier, L. R. Dalton, W. Wang, Y. Shi, “Demonstration of 110 GHz electro-optic polymer modulators,” Appl. Phys. Lett. 70, 3335–3337 (1997).
[CrossRef]

Q. Zhang, M. Canva, G. Stegeman, “Wavelength dependence of 4-dimethylamino-4′-nitrostilbene polymer thin film photodegradation,” Appl. Phys. Lett. 73, 912–914 (1998).
[CrossRef]

J. Vydra, H. Beisinghoff, T. Tschudi, M. Eich, “Photodecay mechanisms in side chain nonlinear optical polymethacrylates,” Appl. Phys. Lett. 69, 1035–1037 (1996).
[CrossRef]

J.-J. Kim, T. Zyung, W.-Y. Hwang, “Photochemically formed refractive index profiles in nonlinear optical polymer thin films,” Appl. Phys. Lett. 64, 3488–3490 (1994).
[CrossRef]

Electron. Lett. (1)

Th. Knoche, L. Müller, R. Klein, A. Neyer, “Low loss polymer waveguides at 1300 and 1500 nm using halogenated acrylates,” Electron. Lett. 32, 1284–1285 (1996).
[CrossRef]

IEEE Photon. Technol. Lett. (1)

W.-Y. Hwang, M.-C. Oh, H.-M. Lee, H. Park, J.-J. Kim, “Polymeric 2 × 2 electrooptic switch consisting of asymmetric Y junctions and Mach–Zehnder interferometer,” IEEE Photon. Technol. Lett. 9, 761–763 (1997).
[CrossRef]

IEEE Trans. Components Packag. Manuf. Technol. Part B (1)

C. F. Kane, R. R. Krchnavek, “Processing and characterization of benzocyclobutene optical waveguides,” IEEE Trans. Components Packag. Manuf. Technol. Part B 18, 565–571 (1995).
[CrossRef]

J. Am. Chem. Soc. (1)

M. Szablewski, P. R. Thomas, A. Thornton, D. Bloor, G. H. Cross, J. M. Cole, J. A. K. Howard, M. Malagoli, F. Meyers, J.-L. Brédas, W. Wenseleers, E. Goovaerts, “Highly dipolar, optically nonlinear adducts of tetracyano-p-quinodimethane: synthesis, physical characterization, and theoretical aspects,” J. Am. Chem. Soc. 119, 3144–3154 (1997).
[CrossRef]

J. Appl. Phys. (3)

A. Costela, I. Garcia-Moreno, J. Barraso, R. Sastre, “Laser performance of Coumarin 540A dye molecules in polymeric host media with different viscosities: from liquid solution to solid polymer matrix,” J. Appl. Phys. 83, 650–660 (1998).
[CrossRef]

T. Watanabe, M. Hikita, M. Amano, Y. Shuto, S. Tomaru, “Vertically stacked coupler and serially grafted waveguide: hybrid waveguide structures formed using an electro-optic polymer,” J. Appl. Phys. 83, 639–649 (1998).
[CrossRef]

M. A. Mortazavi, H. N. Yoon, C. C. Teng, “Optical power handling properties of polymeric nonlinear optical waveguides,” J. Appl. Phys. 74, 4871–4876 (1993).
[CrossRef]

J. Lightwave Technol. (3)

B. L. Booth, “Low loss channel waveguides in polymers,” J. Lightwave Technol. 7, 1445–1453 (1989).
[CrossRef]

M. Usui, M. Hikita, T. Watanabe, M. Amano, S. Sugawara, S. Hayashida, S. Imamura, “Low-loss passive polymer optical waveguides with high environmental stability,” J. Lightwave Technol. 14, 2338–2343 (1996).
[CrossRef]

J. Kobayashi, T. Matsuura, S. Sasaki, T. Maruno, “Directional couplers using fluorinated polyimide waveguides,” J. Lightwave Technol. 16, 610–614 (1998).
[CrossRef]

J. Opt. Soc. Am. B (1)

J. Org. Chem. (1)

M. Szablewski, “Novel reactions of TCNQ: formation of zwitterions for nonlinear optics by reaction with examines,” J. Org. Chem. 59, 954–956 (1994).
[CrossRef]

Nonlin. Opt. (2)

M. Dumont, Z. Sekkat, R. Loucif-Saibi, K. Nakatini, J. A. Delaire, “Photoisomerization, photoinduced orientation and orientational relaxation in polymeric films,” Nonlin. Opt. 5, 395–406 (1993).

R. A. Norwood, D. R. Holcomb, F. F. So, “Polymers for nonlinear optics: absorption, two-photon absorption and photodegradation,” Nonlin. Opt. 6, 193–204 (1993).

Synth. Met. (1)

A. Dubois, M. Canva, A. Brun, F. Chaput, J.-P. Boilot, “Enhanced photostability of dye molecules trapped in solid xerogel matrices,” Synth. Met. 81, 305–308 (1996).
[CrossRef]

Other (5)

R. M. Siverstein, G. C. Basster, T. C. Morrill, Spectrometric Identification of Organic Compounds (Wiley, New York, 1981).

P. R. Ogilby, M. Kristiansen, D. O. Martine, R. D. Scurlock, V. L. Taylor, R. L. Clough, “Formation and removal of singlet (a′Δg) oxygen in bulk polymers: events that may influence photodegradation,” in Polymer Durability: Degradation, Durability and Lifetime Prediction, R. L. Clough, N. C. Billingham, K. T. Gillen, eds. (American Chemical Society, Washington, D.C., 1996), pp. 113–126.

C. Bosshard, K. Sutter, Ph. Prêtre, J. Hulliger, M. Flörsheimer, P. Kaatz, P. Günter, Organic Nonlinear Optical Materials, Vol. 1 of Advances in Nonlinear Optics (Gordon & Breach, Amsterdam, 1995), p 181.

D. S. Chemla, J. Zyss, Nonlinear Optical Properties of Organic Molecules and Crystals (Academic, London, 1986), Vol. 1.

L. A. Hornak, Polymers for lightwave and integrated optics (Marcel Dekker, New York, 1992), Chaps. 1 and 2.

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Figures (11)

Fig. 1
Fig. 1

Molecular structures of the DEMI-series materials.

Fig. 2
Fig. 2

UV–visible–near-IR absorption spectra of DEMI-series materials doped (1% w/w) in PMMA and baked at 60 °C in vacuum for 48 h. 1, DEMI; 2, ultra-DEMI; 3, dicyclohexyl-DEMI.

Fig. 3
Fig. 3

UV–visible absorption spectra of unirradiated (t = 0) and irradiated ultra-DEMI at 632.8-nm wavelength in air (∼20 °C) for several lengths of time (indicated in hours).

Fig. 4
Fig. 4

DEMI-series materials’ degradation at 632.8 nm (2.66 × 1015 photons/s) in air (∼20 °C): (1) DEMI, (2) ultra-DEMI, (3) dicyclohexyl-DEMI.

Fig. 5
Fig. 5

DEMI-series materials’ degradation at 780.0 nm (2.66 × 1015 photons/s) in air (∼20 °C): (1) DEMI, (2) ultra-DEMI, (3) dicyclohexyl-DEMI.

Fig. 6
Fig. 6

DEMI-series materials’ degradation at 940.0 nm (2.127 × 1016 photons/s) in air (∼20 °C): (1) DEMI, (2) ultra-DEMI, (3) dicyclohexyl-DEMI.

Fig. 7
Fig. 7

DEMI-series materials’ degradation at 632.8 nm (2.66 × 1015 photons/s) in vacuum (<10 mbars, ∼20 °C): (1) DEMI, (2) ultra-DEMI, (3) dicyclohexyl-DEMI.

Fig. 8
Fig. 8

DEMI-series materials’ degradation at 632.8 nm (2.66 × 1015 photons/s) in nitrogen (∼1 atm, ∼20 °C): (1) DEMI, (2) ultra-DEMI, (3) dicyclohexyl-DEMI.

Fig. 9
Fig. 9

Typical fit of the transmission-versus-degradation time for ultra-DEMI.

Fig. 10
Fig. 10

IR spectra of unirradiated ultra-DEMI doped in poly(N-vinylcarbazole) (PVK) and irradiated in air at 632.8- and 780.0-nm wavelengths.

Fig. 11
Fig. 11

Representation of a possible route to oxidation of the dye molecules. Production of singlet oxygen by a photoexcited dye molecule (D*) can lead to oxidation of the molecule. The products include carbonyl groups and free radicals; the latter can enter an auto-oxidation cycle, leading to further thermo-oxidation. 1D, dye in singlet ground state; 1D*, dye in excited singlet state; 3D*, dye in excited triplet state; 1O2*, singlet oxygen (excited state); 3O2, triplet oxygen (ground state).

Tables (3)

Tables Icon

Table 1 Peak Wavelengths of the DEMI-Series Materials in PMMA Thin Films

Tables Icon

Table 2 Calculation of Coupling Efficiency η of Two-Prism Couplinga

Tables Icon

Table 3 B Factor for DEMI-Series Materials Doped in PMMA and Degraded at Various Wavelengths in Air at Room Temperature (∼20 °C)

Equations (4)

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

ηtotal=η1η2,
Tt=T1+T/T0-1exp-βE,
βE=σ1n0B-1t,
Bdicyclohexyl-DEMI>Bultra-DEMI>BDEMI.

Metrics