Abstract

Polymer-dispersed perylene di-imide dye photodegradation is investigated by monitoring the fluorescence intensity as a function of 532  nm laser pulses. Anaerobically irradiated polymer–dye films exhibited an accelerated decrease in fluorescence intensity, which was partially recovered upon exposure to oxygen. Decelerated photodegradation rates were observed for perylene di-imide ethanol solutions upon the addition of a singlet oxygen quenching antioxidant. These observations suggest reversible photoreduction and type II photo-oxidation as important photodegradation mechanisms. Type II photo-oxidation for perylene red 532  nm irradiation is supported by a singlet oxygen quantum yield of 0.09±0.03, determined via detection of time-resolved O2(a1ΔgX3g   ) infrared phosphorescence.

© 2006 Optical Society of America

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  1. T. Nhung, M. Canva, F. Chaput, H. Goudket, G. Roger, A. Brun, D. Manh, N. Hung, and J. Boilot, "Dye energy transfer in xerogel matrices and application to solid-state dye lasers," Opti. Commun. 232, 343-351 (2004).
    [CrossRef]
  2. D. Su, Y. Yang, G. Qian, Z. Wang, and M. Wang, "Influence of energy transfer on fluorescence and lasing properties of various laser dyes co-doped in ORMOSILs," Chem. Phys. Lett. 397, 397-401 (2004).
    [CrossRef]
  3. Y. Yang, G. Qian, D. Su, Z. Wang, and M. Wang, "Energy transfer mechanism between laser dyes doped in ORMOSILs," Chem. Phys. Lett. 402, 389-394 (2005).
    [CrossRef]
  4. A. Dubois, M. Canva, A. Brun, F. Chaput, and J. Boilot, "Enhanced photostability of dye molecules trapped in solid xerogel matrixes," Synth. Met. 81, 305-308 (1996).
    [CrossRef]
  5. Y. Yang, M. Wang, G. Qian, Z. Wang, and X. Fan, "Laser properties and photostabilities of laser dyes doped in ORMOSILs," Opt. Mater. 24, 621-628 (2004).
    [CrossRef]
  6. G. Qian, Y. Yang, Z. Wang, C. Yang, Z. Yang, and M. Wang, "Photostability of perylene orange, perylene red and pyrromethene 567 laser dyes in various precursors derived gel glasses," Chem. Phys. Lett. 368, 555-560 (2003).
    [CrossRef]
  7. P. Schlup, G. W. Baxter, and I. T. McKinnie, "Single-mode visible and mid-infrared periodically poled lithium niobate optical parametric oscillator amplified in perylene red doped poly(methyl methacrylate)," Opt. Commun. 184, 225-230 (2000).
    [CrossRef]
  8. N. N. Barashkov and O. A. Gunder, Fluorescent Polymers (Ellis Horwood, 1994).
  9. M. Tasaki, A. Ichikawa, T. Odaki, and K. Takagi, "Transparent coating member for light-emitting diodes and a fluorescent color light source," U.S. patent 6,319,425, (20 November 2001).
  10. J. Y. Kim and A. J. Bard, "Organic donor/acceptor heterojunction photovoltaic devices based on zinc phthalocyanine and a liquid crystalline perylene di-imide," Chem. Phys. Lett. 383, 11-15 (2004).
    [CrossRef]
  11. C. W. Tang, "Two-layer organic photovoltaic cell," Appl. Phy. Lett. 48, 183-185 (1986).
    [CrossRef]
  12. G. Horowitz, F. Kouki, P. Spearman, D. Fichou, C. Nogues, X. Pan, and F. Garnier, "Evidence for n-type conduction in a perylene tetracarboxylic di-imide derivative," Adv. Mater. 8, 242-245 (1996).
    [CrossRef]
  13. M. S. Mackey and W. N. Sisk, "Photostability of pyrromethene 567 laser dye solutions via photoluminescence measurements," Dyes Pigm. 51, 79-85 (2001).
    [CrossRef]
  14. M. D. Rahn, T. A. King, A. A. Gorman, and I. Hamblett, "Photostability enhancement of Pyrromethene 567 and Perylene Orange in oxygen-free liquid and solid dye lasers," Appl. Opt. 36, 5862-5871 (1997).
    [CrossRef] [PubMed]
  15. G. Jones II, O. Klueva, S. Kumar, and D. Pacheco, "Photochemical and lasing properties of pyrromethene dyes," in Solid State Lasers X, RichardScheps, ed., Proc. SPIE 4267, 24-35 (2001).
  16. G. Seybold and G. Wagenblast, "New perylene and violanthrone dyestuffs for fluorescent collectors," Dyes Pigm. 11, 303-317 (1989).
    [CrossRef]
  17. K. Ocka, N. Job, J. Kim, S. Kim, and K. Koh, "Thin film optical waveguide type UV sensor using a photochromic molecular device, spirooxazine," Synth. Met. 117, 131-133 (2001).
    [CrossRef]
  18. M. C. Castex, C. Olivero, A. Fischer, S. Mousel, J. Michelon, D. Ades, and A. Siove, "Polycarbazoles microcavities: towards plastic blue lasers," Appl. Surf. Sci. 197-198, 822-825 (2002).
    [CrossRef]
  19. F. Wilkinson, P. Helman, and A. B. Ross, "Rate constants for the decay and reactions of the lowest electronically excited singlet state of molecular oxygen in solution. An expanded and revised compilation," J. Phys. Chem. Ref. Data 24, 663-1021 (1995).
    [CrossRef]
  20. G. S. Egerton and A. G. Morgan, "Photochemistry of dyes. I. Fundamental principles," (J. Soc. Dyers Colour. 86, 79-831970).
  21. L. Chen, L. A. Lucia, E. R. Gaillard, H. Icil, S. Icli, and D. G. Whitten, "Photo-oxidation of a conjugated diene by an exciplex mechanism: amplification via radical chain reactions in the perylene di-imide-photosensitized oxidation of α-terpinene," J. Phys. Chem. A 102, 9095-9098 (1998).
    [CrossRef]
  22. S. Icli, S. Demic, B. Dindar, A. O. Doroshenko, and C. Timur, "Photophysical and photochemical properties of a water-soluble perylene di-imide derivative," J. Photochem. Photobiol. , A 136, 15-24 (2000).
    [CrossRef]
  23. H. Dincalp and S. Icli, "Photosynthesis of rose oxide by concentrated sunlight in the absence of singlet oxygen," J. Photochem. Photobiol. , A 141, 147-151 (2001).
    [CrossRef]
  24. R. T. Morrison and R. N. Boyd, Organic Chemistry, 5th ed. (Allyn and Bacon, 1987).
  25. D. Gosztola, M. P. Niemczyk, W. Svec, A. S. Lukasand, and M. R. Wasielewski, "Excited Doublet States of Electrochemically Generated Aromatic Imide and Di-imide Radical Anions," J. Phys. Chem. A 104, 6545-6551 (2000).
    [CrossRef]
  26. W. N. Sisk and W. Sanders, "The concentration dependence of the normalized photostability of 1,3,5,7,8-pentamethyl-2,6-di-t-butylpyrromethene-difluoroborate complex (PM597) methanol solutions," J. Photochem. Photobiol. , A 167, 185-189 (2004).
    [CrossRef]
  27. A. A. Gorman, I. Hamblett, T. A. King, and M. D. Rahn, "A pulse radiolysis and pulsed laser study of the pyrromethene 567 triplet state," J. Photochem. Photobiol. , A 130, 127-132 (2000).
    [CrossRef]
  28. N. Tanaka and W. N. Sisk, "The photodegradation of pyrromethene 567 and pyrromethene 597 by pyrromethene 546," J. Photochem. Photobiol. , A 172, 109-114 (2005).
    [CrossRef]
  29. G. H. Kim, J. Oh, Y. S. Yang, L. Do, and K. S. Suh, "Lamination process encapsulation for longevity of plastic-based organic light-emitting devices," Thin Solid Films 467, 1-3 (2004).
    [CrossRef]
  30. P. L. Rendu, T. P. Nguyen, and L. Carrois, "Cellulose acetate and PVDC used as protective layers for organic diodes," Synth. Met. 138, 285-288 (2003).
    [CrossRef]
  31. K. M. Kim, B. J. Jang, W. S. Cho, and S. H. Ju, "The property of encapsulation using thin film multi layer for application to organic light emitting device," Curr. Appl. Phys. 5, 64-66 (2005).
    [CrossRef]

2005 (3)

Y. Yang, G. Qian, D. Su, Z. Wang, and M. Wang, "Energy transfer mechanism between laser dyes doped in ORMOSILs," Chem. Phys. Lett. 402, 389-394 (2005).
[CrossRef]

N. Tanaka and W. N. Sisk, "The photodegradation of pyrromethene 567 and pyrromethene 597 by pyrromethene 546," J. Photochem. Photobiol. , A 172, 109-114 (2005).
[CrossRef]

K. M. Kim, B. J. Jang, W. S. Cho, and S. H. Ju, "The property of encapsulation using thin film multi layer for application to organic light emitting device," Curr. Appl. Phys. 5, 64-66 (2005).
[CrossRef]

2004 (6)

G. H. Kim, J. Oh, Y. S. Yang, L. Do, and K. S. Suh, "Lamination process encapsulation for longevity of plastic-based organic light-emitting devices," Thin Solid Films 467, 1-3 (2004).
[CrossRef]

W. N. Sisk and W. Sanders, "The concentration dependence of the normalized photostability of 1,3,5,7,8-pentamethyl-2,6-di-t-butylpyrromethene-difluoroborate complex (PM597) methanol solutions," J. Photochem. Photobiol. , A 167, 185-189 (2004).
[CrossRef]

T. Nhung, M. Canva, F. Chaput, H. Goudket, G. Roger, A. Brun, D. Manh, N. Hung, and J. Boilot, "Dye energy transfer in xerogel matrices and application to solid-state dye lasers," Opti. Commun. 232, 343-351 (2004).
[CrossRef]

D. Su, Y. Yang, G. Qian, Z. Wang, and M. Wang, "Influence of energy transfer on fluorescence and lasing properties of various laser dyes co-doped in ORMOSILs," Chem. Phys. Lett. 397, 397-401 (2004).
[CrossRef]

Y. Yang, M. Wang, G. Qian, Z. Wang, and X. Fan, "Laser properties and photostabilities of laser dyes doped in ORMOSILs," Opt. Mater. 24, 621-628 (2004).
[CrossRef]

J. Y. Kim and A. J. Bard, "Organic donor/acceptor heterojunction photovoltaic devices based on zinc phthalocyanine and a liquid crystalline perylene di-imide," Chem. Phys. Lett. 383, 11-15 (2004).
[CrossRef]

2003 (2)

G. Qian, Y. Yang, Z. Wang, C. Yang, Z. Yang, and M. Wang, "Photostability of perylene orange, perylene red and pyrromethene 567 laser dyes in various precursors derived gel glasses," Chem. Phys. Lett. 368, 555-560 (2003).
[CrossRef]

P. L. Rendu, T. P. Nguyen, and L. Carrois, "Cellulose acetate and PVDC used as protective layers for organic diodes," Synth. Met. 138, 285-288 (2003).
[CrossRef]

2002 (1)

M. C. Castex, C. Olivero, A. Fischer, S. Mousel, J. Michelon, D. Ades, and A. Siove, "Polycarbazoles microcavities: towards plastic blue lasers," Appl. Surf. Sci. 197-198, 822-825 (2002).
[CrossRef]

2001 (4)

K. Ocka, N. Job, J. Kim, S. Kim, and K. Koh, "Thin film optical waveguide type UV sensor using a photochromic molecular device, spirooxazine," Synth. Met. 117, 131-133 (2001).
[CrossRef]

M. Tasaki, A. Ichikawa, T. Odaki, and K. Takagi, "Transparent coating member for light-emitting diodes and a fluorescent color light source," U.S. patent 6,319,425, (20 November 2001).

M. S. Mackey and W. N. Sisk, "Photostability of pyrromethene 567 laser dye solutions via photoluminescence measurements," Dyes Pigm. 51, 79-85 (2001).
[CrossRef]

H. Dincalp and S. Icli, "Photosynthesis of rose oxide by concentrated sunlight in the absence of singlet oxygen," J. Photochem. Photobiol. , A 141, 147-151 (2001).
[CrossRef]

2000 (4)

D. Gosztola, M. P. Niemczyk, W. Svec, A. S. Lukasand, and M. R. Wasielewski, "Excited Doublet States of Electrochemically Generated Aromatic Imide and Di-imide Radical Anions," J. Phys. Chem. A 104, 6545-6551 (2000).
[CrossRef]

A. A. Gorman, I. Hamblett, T. A. King, and M. D. Rahn, "A pulse radiolysis and pulsed laser study of the pyrromethene 567 triplet state," J. Photochem. Photobiol. , A 130, 127-132 (2000).
[CrossRef]

S. Icli, S. Demic, B. Dindar, A. O. Doroshenko, and C. Timur, "Photophysical and photochemical properties of a water-soluble perylene di-imide derivative," J. Photochem. Photobiol. , A 136, 15-24 (2000).
[CrossRef]

P. Schlup, G. W. Baxter, and I. T. McKinnie, "Single-mode visible and mid-infrared periodically poled lithium niobate optical parametric oscillator amplified in perylene red doped poly(methyl methacrylate)," Opt. Commun. 184, 225-230 (2000).
[CrossRef]

1998 (1)

L. Chen, L. A. Lucia, E. R. Gaillard, H. Icil, S. Icli, and D. G. Whitten, "Photo-oxidation of a conjugated diene by an exciplex mechanism: amplification via radical chain reactions in the perylene di-imide-photosensitized oxidation of α-terpinene," J. Phys. Chem. A 102, 9095-9098 (1998).
[CrossRef]

1997 (1)

1996 (2)

G. Horowitz, F. Kouki, P. Spearman, D. Fichou, C. Nogues, X. Pan, and F. Garnier, "Evidence for n-type conduction in a perylene tetracarboxylic di-imide derivative," Adv. Mater. 8, 242-245 (1996).
[CrossRef]

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

1995 (1)

F. Wilkinson, P. Helman, and A. B. Ross, "Rate constants for the decay and reactions of the lowest electronically excited singlet state of molecular oxygen in solution. An expanded and revised compilation," J. Phys. Chem. Ref. Data 24, 663-1021 (1995).
[CrossRef]

1989 (1)

G. Seybold and G. Wagenblast, "New perylene and violanthrone dyestuffs for fluorescent collectors," Dyes Pigm. 11, 303-317 (1989).
[CrossRef]

1986 (1)

C. W. Tang, "Two-layer organic photovoltaic cell," Appl. Phy. Lett. 48, 183-185 (1986).
[CrossRef]

Ades, D.

M. C. Castex, C. Olivero, A. Fischer, S. Mousel, J. Michelon, D. Ades, and A. Siove, "Polycarbazoles microcavities: towards plastic blue lasers," Appl. Surf. Sci. 197-198, 822-825 (2002).
[CrossRef]

Barashkov, N. N.

N. N. Barashkov and O. A. Gunder, Fluorescent Polymers (Ellis Horwood, 1994).

Bard, A. J.

J. Y. Kim and A. J. Bard, "Organic donor/acceptor heterojunction photovoltaic devices based on zinc phthalocyanine and a liquid crystalline perylene di-imide," Chem. Phys. Lett. 383, 11-15 (2004).
[CrossRef]

Baxter, G. W.

P. Schlup, G. W. Baxter, and I. T. McKinnie, "Single-mode visible and mid-infrared periodically poled lithium niobate optical parametric oscillator amplified in perylene red doped poly(methyl methacrylate)," Opt. Commun. 184, 225-230 (2000).
[CrossRef]

Boilot, J.

T. Nhung, M. Canva, F. Chaput, H. Goudket, G. Roger, A. Brun, D. Manh, N. Hung, and J. Boilot, "Dye energy transfer in xerogel matrices and application to solid-state dye lasers," Opti. Commun. 232, 343-351 (2004).
[CrossRef]

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

Boyd, R. N.

R. T. Morrison and R. N. Boyd, Organic Chemistry, 5th ed. (Allyn and Bacon, 1987).

Brun, A.

T. Nhung, M. Canva, F. Chaput, H. Goudket, G. Roger, A. Brun, D. Manh, N. Hung, and J. Boilot, "Dye energy transfer in xerogel matrices and application to solid-state dye lasers," Opti. Commun. 232, 343-351 (2004).
[CrossRef]

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

Canva, M.

T. Nhung, M. Canva, F. Chaput, H. Goudket, G. Roger, A. Brun, D. Manh, N. Hung, and J. Boilot, "Dye energy transfer in xerogel matrices and application to solid-state dye lasers," Opti. Commun. 232, 343-351 (2004).
[CrossRef]

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

Carrois, L.

P. L. Rendu, T. P. Nguyen, and L. Carrois, "Cellulose acetate and PVDC used as protective layers for organic diodes," Synth. Met. 138, 285-288 (2003).
[CrossRef]

Castex, M. C.

M. C. Castex, C. Olivero, A. Fischer, S. Mousel, J. Michelon, D. Ades, and A. Siove, "Polycarbazoles microcavities: towards plastic blue lasers," Appl. Surf. Sci. 197-198, 822-825 (2002).
[CrossRef]

Chaput, F.

T. Nhung, M. Canva, F. Chaput, H. Goudket, G. Roger, A. Brun, D. Manh, N. Hung, and J. Boilot, "Dye energy transfer in xerogel matrices and application to solid-state dye lasers," Opti. Commun. 232, 343-351 (2004).
[CrossRef]

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

Chen, L.

L. Chen, L. A. Lucia, E. R. Gaillard, H. Icil, S. Icli, and D. G. Whitten, "Photo-oxidation of a conjugated diene by an exciplex mechanism: amplification via radical chain reactions in the perylene di-imide-photosensitized oxidation of α-terpinene," J. Phys. Chem. A 102, 9095-9098 (1998).
[CrossRef]

Cho, W. S.

K. M. Kim, B. J. Jang, W. S. Cho, and S. H. Ju, "The property of encapsulation using thin film multi layer for application to organic light emitting device," Curr. Appl. Phys. 5, 64-66 (2005).
[CrossRef]

Demic, S.

S. Icli, S. Demic, B. Dindar, A. O. Doroshenko, and C. Timur, "Photophysical and photochemical properties of a water-soluble perylene di-imide derivative," J. Photochem. Photobiol. , A 136, 15-24 (2000).
[CrossRef]

Dincalp, H.

H. Dincalp and S. Icli, "Photosynthesis of rose oxide by concentrated sunlight in the absence of singlet oxygen," J. Photochem. Photobiol. , A 141, 147-151 (2001).
[CrossRef]

Dindar, B.

S. Icli, S. Demic, B. Dindar, A. O. Doroshenko, and C. Timur, "Photophysical and photochemical properties of a water-soluble perylene di-imide derivative," J. Photochem. Photobiol. , A 136, 15-24 (2000).
[CrossRef]

Do, L.

G. H. Kim, J. Oh, Y. S. Yang, L. Do, and K. S. Suh, "Lamination process encapsulation for longevity of plastic-based organic light-emitting devices," Thin Solid Films 467, 1-3 (2004).
[CrossRef]

Doroshenko, A. O.

S. Icli, S. Demic, B. Dindar, A. O. Doroshenko, and C. Timur, "Photophysical and photochemical properties of a water-soluble perylene di-imide derivative," J. Photochem. Photobiol. , A 136, 15-24 (2000).
[CrossRef]

Dubois, A.

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

Egerton, G. S.

G. S. Egerton and A. G. Morgan, "Photochemistry of dyes. I. Fundamental principles," (J. Soc. Dyers Colour. 86, 79-831970).

Fan, X.

Y. Yang, M. Wang, G. Qian, Z. Wang, and X. Fan, "Laser properties and photostabilities of laser dyes doped in ORMOSILs," Opt. Mater. 24, 621-628 (2004).
[CrossRef]

Fichou, D.

G. Horowitz, F. Kouki, P. Spearman, D. Fichou, C. Nogues, X. Pan, and F. Garnier, "Evidence for n-type conduction in a perylene tetracarboxylic di-imide derivative," Adv. Mater. 8, 242-245 (1996).
[CrossRef]

Fischer, A.

M. C. Castex, C. Olivero, A. Fischer, S. Mousel, J. Michelon, D. Ades, and A. Siove, "Polycarbazoles microcavities: towards plastic blue lasers," Appl. Surf. Sci. 197-198, 822-825 (2002).
[CrossRef]

Gaillard, E. R.

L. Chen, L. A. Lucia, E. R. Gaillard, H. Icil, S. Icli, and D. G. Whitten, "Photo-oxidation of a conjugated diene by an exciplex mechanism: amplification via radical chain reactions in the perylene di-imide-photosensitized oxidation of α-terpinene," J. Phys. Chem. A 102, 9095-9098 (1998).
[CrossRef]

Garnier, F.

G. Horowitz, F. Kouki, P. Spearman, D. Fichou, C. Nogues, X. Pan, and F. Garnier, "Evidence for n-type conduction in a perylene tetracarboxylic di-imide derivative," Adv. Mater. 8, 242-245 (1996).
[CrossRef]

Gorman, A. A.

A. A. Gorman, I. Hamblett, T. A. King, and M. D. Rahn, "A pulse radiolysis and pulsed laser study of the pyrromethene 567 triplet state," J. Photochem. Photobiol. , A 130, 127-132 (2000).
[CrossRef]

M. D. Rahn, T. A. King, A. A. Gorman, and I. Hamblett, "Photostability enhancement of Pyrromethene 567 and Perylene Orange in oxygen-free liquid and solid dye lasers," Appl. Opt. 36, 5862-5871 (1997).
[CrossRef] [PubMed]

Gosztola, D.

D. Gosztola, M. P. Niemczyk, W. Svec, A. S. Lukasand, and M. R. Wasielewski, "Excited Doublet States of Electrochemically Generated Aromatic Imide and Di-imide Radical Anions," J. Phys. Chem. A 104, 6545-6551 (2000).
[CrossRef]

Goudket, H.

T. Nhung, M. Canva, F. Chaput, H. Goudket, G. Roger, A. Brun, D. Manh, N. Hung, and J. Boilot, "Dye energy transfer in xerogel matrices and application to solid-state dye lasers," Opti. Commun. 232, 343-351 (2004).
[CrossRef]

Gunder, O. A.

N. N. Barashkov and O. A. Gunder, Fluorescent Polymers (Ellis Horwood, 1994).

Hamblett, I.

A. A. Gorman, I. Hamblett, T. A. King, and M. D. Rahn, "A pulse radiolysis and pulsed laser study of the pyrromethene 567 triplet state," J. Photochem. Photobiol. , A 130, 127-132 (2000).
[CrossRef]

M. D. Rahn, T. A. King, A. A. Gorman, and I. Hamblett, "Photostability enhancement of Pyrromethene 567 and Perylene Orange in oxygen-free liquid and solid dye lasers," Appl. Opt. 36, 5862-5871 (1997).
[CrossRef] [PubMed]

Helman, P.

F. Wilkinson, P. Helman, and A. B. Ross, "Rate constants for the decay and reactions of the lowest electronically excited singlet state of molecular oxygen in solution. An expanded and revised compilation," J. Phys. Chem. Ref. Data 24, 663-1021 (1995).
[CrossRef]

Horowitz, G.

G. Horowitz, F. Kouki, P. Spearman, D. Fichou, C. Nogues, X. Pan, and F. Garnier, "Evidence for n-type conduction in a perylene tetracarboxylic di-imide derivative," Adv. Mater. 8, 242-245 (1996).
[CrossRef]

Hung, N.

T. Nhung, M. Canva, F. Chaput, H. Goudket, G. Roger, A. Brun, D. Manh, N. Hung, and J. Boilot, "Dye energy transfer in xerogel matrices and application to solid-state dye lasers," Opti. Commun. 232, 343-351 (2004).
[CrossRef]

Ichikawa, A.

M. Tasaki, A. Ichikawa, T. Odaki, and K. Takagi, "Transparent coating member for light-emitting diodes and a fluorescent color light source," U.S. patent 6,319,425, (20 November 2001).

Icil, H.

L. Chen, L. A. Lucia, E. R. Gaillard, H. Icil, S. Icli, and D. G. Whitten, "Photo-oxidation of a conjugated diene by an exciplex mechanism: amplification via radical chain reactions in the perylene di-imide-photosensitized oxidation of α-terpinene," J. Phys. Chem. A 102, 9095-9098 (1998).
[CrossRef]

Icli, S.

H. Dincalp and S. Icli, "Photosynthesis of rose oxide by concentrated sunlight in the absence of singlet oxygen," J. Photochem. Photobiol. , A 141, 147-151 (2001).
[CrossRef]

S. Icli, S. Demic, B. Dindar, A. O. Doroshenko, and C. Timur, "Photophysical and photochemical properties of a water-soluble perylene di-imide derivative," J. Photochem. Photobiol. , A 136, 15-24 (2000).
[CrossRef]

L. Chen, L. A. Lucia, E. R. Gaillard, H. Icil, S. Icli, and D. G. Whitten, "Photo-oxidation of a conjugated diene by an exciplex mechanism: amplification via radical chain reactions in the perylene di-imide-photosensitized oxidation of α-terpinene," J. Phys. Chem. A 102, 9095-9098 (1998).
[CrossRef]

Jang, B. J.

K. M. Kim, B. J. Jang, W. S. Cho, and S. H. Ju, "The property of encapsulation using thin film multi layer for application to organic light emitting device," Curr. Appl. Phys. 5, 64-66 (2005).
[CrossRef]

Job, N.

K. Ocka, N. Job, J. Kim, S. Kim, and K. Koh, "Thin film optical waveguide type UV sensor using a photochromic molecular device, spirooxazine," Synth. Met. 117, 131-133 (2001).
[CrossRef]

Jones, G.

G. Jones II, O. Klueva, S. Kumar, and D. Pacheco, "Photochemical and lasing properties of pyrromethene dyes," in Solid State Lasers X, RichardScheps, ed., Proc. SPIE 4267, 24-35 (2001).

Ju, S. H.

K. M. Kim, B. J. Jang, W. S. Cho, and S. H. Ju, "The property of encapsulation using thin film multi layer for application to organic light emitting device," Curr. Appl. Phys. 5, 64-66 (2005).
[CrossRef]

Kim, G. H.

G. H. Kim, J. Oh, Y. S. Yang, L. Do, and K. S. Suh, "Lamination process encapsulation for longevity of plastic-based organic light-emitting devices," Thin Solid Films 467, 1-3 (2004).
[CrossRef]

Kim, J.

K. Ocka, N. Job, J. Kim, S. Kim, and K. Koh, "Thin film optical waveguide type UV sensor using a photochromic molecular device, spirooxazine," Synth. Met. 117, 131-133 (2001).
[CrossRef]

Kim, J. Y.

J. Y. Kim and A. J. Bard, "Organic donor/acceptor heterojunction photovoltaic devices based on zinc phthalocyanine and a liquid crystalline perylene di-imide," Chem. Phys. Lett. 383, 11-15 (2004).
[CrossRef]

Kim, K. M.

K. M. Kim, B. J. Jang, W. S. Cho, and S. H. Ju, "The property of encapsulation using thin film multi layer for application to organic light emitting device," Curr. Appl. Phys. 5, 64-66 (2005).
[CrossRef]

Kim, S.

K. Ocka, N. Job, J. Kim, S. Kim, and K. Koh, "Thin film optical waveguide type UV sensor using a photochromic molecular device, spirooxazine," Synth. Met. 117, 131-133 (2001).
[CrossRef]

King, T. A.

A. A. Gorman, I. Hamblett, T. A. King, and M. D. Rahn, "A pulse radiolysis and pulsed laser study of the pyrromethene 567 triplet state," J. Photochem. Photobiol. , A 130, 127-132 (2000).
[CrossRef]

M. D. Rahn, T. A. King, A. A. Gorman, and I. Hamblett, "Photostability enhancement of Pyrromethene 567 and Perylene Orange in oxygen-free liquid and solid dye lasers," Appl. Opt. 36, 5862-5871 (1997).
[CrossRef] [PubMed]

Klueva, O.

G. Jones II, O. Klueva, S. Kumar, and D. Pacheco, "Photochemical and lasing properties of pyrromethene dyes," in Solid State Lasers X, RichardScheps, ed., Proc. SPIE 4267, 24-35 (2001).

Koh, K.

K. Ocka, N. Job, J. Kim, S. Kim, and K. Koh, "Thin film optical waveguide type UV sensor using a photochromic molecular device, spirooxazine," Synth. Met. 117, 131-133 (2001).
[CrossRef]

Kouki, F.

G. Horowitz, F. Kouki, P. Spearman, D. Fichou, C. Nogues, X. Pan, and F. Garnier, "Evidence for n-type conduction in a perylene tetracarboxylic di-imide derivative," Adv. Mater. 8, 242-245 (1996).
[CrossRef]

Kumar, S.

G. Jones II, O. Klueva, S. Kumar, and D. Pacheco, "Photochemical and lasing properties of pyrromethene dyes," in Solid State Lasers X, RichardScheps, ed., Proc. SPIE 4267, 24-35 (2001).

Lucia, L. A.

L. Chen, L. A. Lucia, E. R. Gaillard, H. Icil, S. Icli, and D. G. Whitten, "Photo-oxidation of a conjugated diene by an exciplex mechanism: amplification via radical chain reactions in the perylene di-imide-photosensitized oxidation of α-terpinene," J. Phys. Chem. A 102, 9095-9098 (1998).
[CrossRef]

Lukasand, A. S.

D. Gosztola, M. P. Niemczyk, W. Svec, A. S. Lukasand, and M. R. Wasielewski, "Excited Doublet States of Electrochemically Generated Aromatic Imide and Di-imide Radical Anions," J. Phys. Chem. A 104, 6545-6551 (2000).
[CrossRef]

Mackey, M. S.

M. S. Mackey and W. N. Sisk, "Photostability of pyrromethene 567 laser dye solutions via photoluminescence measurements," Dyes Pigm. 51, 79-85 (2001).
[CrossRef]

Manh, D.

T. Nhung, M. Canva, F. Chaput, H. Goudket, G. Roger, A. Brun, D. Manh, N. Hung, and J. Boilot, "Dye energy transfer in xerogel matrices and application to solid-state dye lasers," Opti. Commun. 232, 343-351 (2004).
[CrossRef]

McKinnie, I. T.

P. Schlup, G. W. Baxter, and I. T. McKinnie, "Single-mode visible and mid-infrared periodically poled lithium niobate optical parametric oscillator amplified in perylene red doped poly(methyl methacrylate)," Opt. Commun. 184, 225-230 (2000).
[CrossRef]

Michelon, J.

M. C. Castex, C. Olivero, A. Fischer, S. Mousel, J. Michelon, D. Ades, and A. Siove, "Polycarbazoles microcavities: towards plastic blue lasers," Appl. Surf. Sci. 197-198, 822-825 (2002).
[CrossRef]

Morgan, A. G.

G. S. Egerton and A. G. Morgan, "Photochemistry of dyes. I. Fundamental principles," (J. Soc. Dyers Colour. 86, 79-831970).

Morrison, R. T.

R. T. Morrison and R. N. Boyd, Organic Chemistry, 5th ed. (Allyn and Bacon, 1987).

Mousel, S.

M. C. Castex, C. Olivero, A. Fischer, S. Mousel, J. Michelon, D. Ades, and A. Siove, "Polycarbazoles microcavities: towards plastic blue lasers," Appl. Surf. Sci. 197-198, 822-825 (2002).
[CrossRef]

Nguyen, T. P.

P. L. Rendu, T. P. Nguyen, and L. Carrois, "Cellulose acetate and PVDC used as protective layers for organic diodes," Synth. Met. 138, 285-288 (2003).
[CrossRef]

Nhung, T.

T. Nhung, M. Canva, F. Chaput, H. Goudket, G. Roger, A. Brun, D. Manh, N. Hung, and J. Boilot, "Dye energy transfer in xerogel matrices and application to solid-state dye lasers," Opti. Commun. 232, 343-351 (2004).
[CrossRef]

Niemczyk, M. P.

D. Gosztola, M. P. Niemczyk, W. Svec, A. S. Lukasand, and M. R. Wasielewski, "Excited Doublet States of Electrochemically Generated Aromatic Imide and Di-imide Radical Anions," J. Phys. Chem. A 104, 6545-6551 (2000).
[CrossRef]

Nogues, C.

G. Horowitz, F. Kouki, P. Spearman, D. Fichou, C. Nogues, X. Pan, and F. Garnier, "Evidence for n-type conduction in a perylene tetracarboxylic di-imide derivative," Adv. Mater. 8, 242-245 (1996).
[CrossRef]

Ocka, K.

K. Ocka, N. Job, J. Kim, S. Kim, and K. Koh, "Thin film optical waveguide type UV sensor using a photochromic molecular device, spirooxazine," Synth. Met. 117, 131-133 (2001).
[CrossRef]

Odaki, T.

M. Tasaki, A. Ichikawa, T. Odaki, and K. Takagi, "Transparent coating member for light-emitting diodes and a fluorescent color light source," U.S. patent 6,319,425, (20 November 2001).

Oh, J.

G. H. Kim, J. Oh, Y. S. Yang, L. Do, and K. S. Suh, "Lamination process encapsulation for longevity of plastic-based organic light-emitting devices," Thin Solid Films 467, 1-3 (2004).
[CrossRef]

Olivero, C.

M. C. Castex, C. Olivero, A. Fischer, S. Mousel, J. Michelon, D. Ades, and A. Siove, "Polycarbazoles microcavities: towards plastic blue lasers," Appl. Surf. Sci. 197-198, 822-825 (2002).
[CrossRef]

Pacheco, D.

G. Jones II, O. Klueva, S. Kumar, and D. Pacheco, "Photochemical and lasing properties of pyrromethene dyes," in Solid State Lasers X, RichardScheps, ed., Proc. SPIE 4267, 24-35 (2001).

Pan, X.

G. Horowitz, F. Kouki, P. Spearman, D. Fichou, C. Nogues, X. Pan, and F. Garnier, "Evidence for n-type conduction in a perylene tetracarboxylic di-imide derivative," Adv. Mater. 8, 242-245 (1996).
[CrossRef]

Qian, G.

Y. Yang, G. Qian, D. Su, Z. Wang, and M. Wang, "Energy transfer mechanism between laser dyes doped in ORMOSILs," Chem. Phys. Lett. 402, 389-394 (2005).
[CrossRef]

D. Su, Y. Yang, G. Qian, Z. Wang, and M. Wang, "Influence of energy transfer on fluorescence and lasing properties of various laser dyes co-doped in ORMOSILs," Chem. Phys. Lett. 397, 397-401 (2004).
[CrossRef]

Y. Yang, M. Wang, G. Qian, Z. Wang, and X. Fan, "Laser properties and photostabilities of laser dyes doped in ORMOSILs," Opt. Mater. 24, 621-628 (2004).
[CrossRef]

G. Qian, Y. Yang, Z. Wang, C. Yang, Z. Yang, and M. Wang, "Photostability of perylene orange, perylene red and pyrromethene 567 laser dyes in various precursors derived gel glasses," Chem. Phys. Lett. 368, 555-560 (2003).
[CrossRef]

Rahn, M. D.

A. A. Gorman, I. Hamblett, T. A. King, and M. D. Rahn, "A pulse radiolysis and pulsed laser study of the pyrromethene 567 triplet state," J. Photochem. Photobiol. , A 130, 127-132 (2000).
[CrossRef]

M. D. Rahn, T. A. King, A. A. Gorman, and I. Hamblett, "Photostability enhancement of Pyrromethene 567 and Perylene Orange in oxygen-free liquid and solid dye lasers," Appl. Opt. 36, 5862-5871 (1997).
[CrossRef] [PubMed]

Rendu, P. L.

P. L. Rendu, T. P. Nguyen, and L. Carrois, "Cellulose acetate and PVDC used as protective layers for organic diodes," Synth. Met. 138, 285-288 (2003).
[CrossRef]

Roger, G.

T. Nhung, M. Canva, F. Chaput, H. Goudket, G. Roger, A. Brun, D. Manh, N. Hung, and J. Boilot, "Dye energy transfer in xerogel matrices and application to solid-state dye lasers," Opti. Commun. 232, 343-351 (2004).
[CrossRef]

Ross, A. B.

F. Wilkinson, P. Helman, and A. B. Ross, "Rate constants for the decay and reactions of the lowest electronically excited singlet state of molecular oxygen in solution. An expanded and revised compilation," J. Phys. Chem. Ref. Data 24, 663-1021 (1995).
[CrossRef]

Sanders, W.

W. N. Sisk and W. Sanders, "The concentration dependence of the normalized photostability of 1,3,5,7,8-pentamethyl-2,6-di-t-butylpyrromethene-difluoroborate complex (PM597) methanol solutions," J. Photochem. Photobiol. , A 167, 185-189 (2004).
[CrossRef]

Schlup, P.

P. Schlup, G. W. Baxter, and I. T. McKinnie, "Single-mode visible and mid-infrared periodically poled lithium niobate optical parametric oscillator amplified in perylene red doped poly(methyl methacrylate)," Opt. Commun. 184, 225-230 (2000).
[CrossRef]

Seybold, G.

G. Seybold and G. Wagenblast, "New perylene and violanthrone dyestuffs for fluorescent collectors," Dyes Pigm. 11, 303-317 (1989).
[CrossRef]

Siove, A.

M. C. Castex, C. Olivero, A. Fischer, S. Mousel, J. Michelon, D. Ades, and A. Siove, "Polycarbazoles microcavities: towards plastic blue lasers," Appl. Surf. Sci. 197-198, 822-825 (2002).
[CrossRef]

Sisk, W. N.

N. Tanaka and W. N. Sisk, "The photodegradation of pyrromethene 567 and pyrromethene 597 by pyrromethene 546," J. Photochem. Photobiol. , A 172, 109-114 (2005).
[CrossRef]

W. N. Sisk and W. Sanders, "The concentration dependence of the normalized photostability of 1,3,5,7,8-pentamethyl-2,6-di-t-butylpyrromethene-difluoroborate complex (PM597) methanol solutions," J. Photochem. Photobiol. , A 167, 185-189 (2004).
[CrossRef]

M. S. Mackey and W. N. Sisk, "Photostability of pyrromethene 567 laser dye solutions via photoluminescence measurements," Dyes Pigm. 51, 79-85 (2001).
[CrossRef]

Spearman, P.

G. Horowitz, F. Kouki, P. Spearman, D. Fichou, C. Nogues, X. Pan, and F. Garnier, "Evidence for n-type conduction in a perylene tetracarboxylic di-imide derivative," Adv. Mater. 8, 242-245 (1996).
[CrossRef]

Su, D.

Y. Yang, G. Qian, D. Su, Z. Wang, and M. Wang, "Energy transfer mechanism between laser dyes doped in ORMOSILs," Chem. Phys. Lett. 402, 389-394 (2005).
[CrossRef]

D. Su, Y. Yang, G. Qian, Z. Wang, and M. Wang, "Influence of energy transfer on fluorescence and lasing properties of various laser dyes co-doped in ORMOSILs," Chem. Phys. Lett. 397, 397-401 (2004).
[CrossRef]

Suh, K. S.

G. H. Kim, J. Oh, Y. S. Yang, L. Do, and K. S. Suh, "Lamination process encapsulation for longevity of plastic-based organic light-emitting devices," Thin Solid Films 467, 1-3 (2004).
[CrossRef]

Svec, W.

D. Gosztola, M. P. Niemczyk, W. Svec, A. S. Lukasand, and M. R. Wasielewski, "Excited Doublet States of Electrochemically Generated Aromatic Imide and Di-imide Radical Anions," J. Phys. Chem. A 104, 6545-6551 (2000).
[CrossRef]

Takagi, K.

M. Tasaki, A. Ichikawa, T. Odaki, and K. Takagi, "Transparent coating member for light-emitting diodes and a fluorescent color light source," U.S. patent 6,319,425, (20 November 2001).

Tanaka, N.

N. Tanaka and W. N. Sisk, "The photodegradation of pyrromethene 567 and pyrromethene 597 by pyrromethene 546," J. Photochem. Photobiol. , A 172, 109-114 (2005).
[CrossRef]

Tang, C. W.

C. W. Tang, "Two-layer organic photovoltaic cell," Appl. Phy. Lett. 48, 183-185 (1986).
[CrossRef]

Tasaki, M.

M. Tasaki, A. Ichikawa, T. Odaki, and K. Takagi, "Transparent coating member for light-emitting diodes and a fluorescent color light source," U.S. patent 6,319,425, (20 November 2001).

Timur, C.

S. Icli, S. Demic, B. Dindar, A. O. Doroshenko, and C. Timur, "Photophysical and photochemical properties of a water-soluble perylene di-imide derivative," J. Photochem. Photobiol. , A 136, 15-24 (2000).
[CrossRef]

Wagenblast, G.

G. Seybold and G. Wagenblast, "New perylene and violanthrone dyestuffs for fluorescent collectors," Dyes Pigm. 11, 303-317 (1989).
[CrossRef]

Wang, M.

Y. Yang, G. Qian, D. Su, Z. Wang, and M. Wang, "Energy transfer mechanism between laser dyes doped in ORMOSILs," Chem. Phys. Lett. 402, 389-394 (2005).
[CrossRef]

Y. Yang, M. Wang, G. Qian, Z. Wang, and X. Fan, "Laser properties and photostabilities of laser dyes doped in ORMOSILs," Opt. Mater. 24, 621-628 (2004).
[CrossRef]

D. Su, Y. Yang, G. Qian, Z. Wang, and M. Wang, "Influence of energy transfer on fluorescence and lasing properties of various laser dyes co-doped in ORMOSILs," Chem. Phys. Lett. 397, 397-401 (2004).
[CrossRef]

G. Qian, Y. Yang, Z. Wang, C. Yang, Z. Yang, and M. Wang, "Photostability of perylene orange, perylene red and pyrromethene 567 laser dyes in various precursors derived gel glasses," Chem. Phys. Lett. 368, 555-560 (2003).
[CrossRef]

Wang, Z.

Y. Yang, G. Qian, D. Su, Z. Wang, and M. Wang, "Energy transfer mechanism between laser dyes doped in ORMOSILs," Chem. Phys. Lett. 402, 389-394 (2005).
[CrossRef]

D. Su, Y. Yang, G. Qian, Z. Wang, and M. Wang, "Influence of energy transfer on fluorescence and lasing properties of various laser dyes co-doped in ORMOSILs," Chem. Phys. Lett. 397, 397-401 (2004).
[CrossRef]

Y. Yang, M. Wang, G. Qian, Z. Wang, and X. Fan, "Laser properties and photostabilities of laser dyes doped in ORMOSILs," Opt. Mater. 24, 621-628 (2004).
[CrossRef]

G. Qian, Y. Yang, Z. Wang, C. Yang, Z. Yang, and M. Wang, "Photostability of perylene orange, perylene red and pyrromethene 567 laser dyes in various precursors derived gel glasses," Chem. Phys. Lett. 368, 555-560 (2003).
[CrossRef]

Wasielewski, M. R.

D. Gosztola, M. P. Niemczyk, W. Svec, A. S. Lukasand, and M. R. Wasielewski, "Excited Doublet States of Electrochemically Generated Aromatic Imide and Di-imide Radical Anions," J. Phys. Chem. A 104, 6545-6551 (2000).
[CrossRef]

Whitten, D. G.

L. Chen, L. A. Lucia, E. R. Gaillard, H. Icil, S. Icli, and D. G. Whitten, "Photo-oxidation of a conjugated diene by an exciplex mechanism: amplification via radical chain reactions in the perylene di-imide-photosensitized oxidation of α-terpinene," J. Phys. Chem. A 102, 9095-9098 (1998).
[CrossRef]

Wilkinson, F.

F. Wilkinson, P. Helman, and A. B. Ross, "Rate constants for the decay and reactions of the lowest electronically excited singlet state of molecular oxygen in solution. An expanded and revised compilation," J. Phys. Chem. Ref. Data 24, 663-1021 (1995).
[CrossRef]

Yang, C.

G. Qian, Y. Yang, Z. Wang, C. Yang, Z. Yang, and M. Wang, "Photostability of perylene orange, perylene red and pyrromethene 567 laser dyes in various precursors derived gel glasses," Chem. Phys. Lett. 368, 555-560 (2003).
[CrossRef]

Yang, Y.

Y. Yang, G. Qian, D. Su, Z. Wang, and M. Wang, "Energy transfer mechanism between laser dyes doped in ORMOSILs," Chem. Phys. Lett. 402, 389-394 (2005).
[CrossRef]

D. Su, Y. Yang, G. Qian, Z. Wang, and M. Wang, "Influence of energy transfer on fluorescence and lasing properties of various laser dyes co-doped in ORMOSILs," Chem. Phys. Lett. 397, 397-401 (2004).
[CrossRef]

Y. Yang, M. Wang, G. Qian, Z. Wang, and X. Fan, "Laser properties and photostabilities of laser dyes doped in ORMOSILs," Opt. Mater. 24, 621-628 (2004).
[CrossRef]

G. Qian, Y. Yang, Z. Wang, C. Yang, Z. Yang, and M. Wang, "Photostability of perylene orange, perylene red and pyrromethene 567 laser dyes in various precursors derived gel glasses," Chem. Phys. Lett. 368, 555-560 (2003).
[CrossRef]

Yang, Y. S.

G. H. Kim, J. Oh, Y. S. Yang, L. Do, and K. S. Suh, "Lamination process encapsulation for longevity of plastic-based organic light-emitting devices," Thin Solid Films 467, 1-3 (2004).
[CrossRef]

Yang, Z.

G. Qian, Y. Yang, Z. Wang, C. Yang, Z. Yang, and M. Wang, "Photostability of perylene orange, perylene red and pyrromethene 567 laser dyes in various precursors derived gel glasses," Chem. Phys. Lett. 368, 555-560 (2003).
[CrossRef]

Adv. Mater. (1)

G. Horowitz, F. Kouki, P. Spearman, D. Fichou, C. Nogues, X. Pan, and F. Garnier, "Evidence for n-type conduction in a perylene tetracarboxylic di-imide derivative," Adv. Mater. 8, 242-245 (1996).
[CrossRef]

Appl. Opt. (1)

Appl. Phy. Lett. (1)

C. W. Tang, "Two-layer organic photovoltaic cell," Appl. Phy. Lett. 48, 183-185 (1986).
[CrossRef]

Appl. Surf. Sci. (1)

M. C. Castex, C. Olivero, A. Fischer, S. Mousel, J. Michelon, D. Ades, and A. Siove, "Polycarbazoles microcavities: towards plastic blue lasers," Appl. Surf. Sci. 197-198, 822-825 (2002).
[CrossRef]

Chem. Phys. Lett. (4)

G. Qian, Y. Yang, Z. Wang, C. Yang, Z. Yang, and M. Wang, "Photostability of perylene orange, perylene red and pyrromethene 567 laser dyes in various precursors derived gel glasses," Chem. Phys. Lett. 368, 555-560 (2003).
[CrossRef]

D. Su, Y. Yang, G. Qian, Z. Wang, and M. Wang, "Influence of energy transfer on fluorescence and lasing properties of various laser dyes co-doped in ORMOSILs," Chem. Phys. Lett. 397, 397-401 (2004).
[CrossRef]

Y. Yang, G. Qian, D. Su, Z. Wang, and M. Wang, "Energy transfer mechanism between laser dyes doped in ORMOSILs," Chem. Phys. Lett. 402, 389-394 (2005).
[CrossRef]

J. Y. Kim and A. J. Bard, "Organic donor/acceptor heterojunction photovoltaic devices based on zinc phthalocyanine and a liquid crystalline perylene di-imide," Chem. Phys. Lett. 383, 11-15 (2004).
[CrossRef]

Curr. Appl. Phys. (1)

K. M. Kim, B. J. Jang, W. S. Cho, and S. H. Ju, "The property of encapsulation using thin film multi layer for application to organic light emitting device," Curr. Appl. Phys. 5, 64-66 (2005).
[CrossRef]

Dyes Pigm. (2)

G. Seybold and G. Wagenblast, "New perylene and violanthrone dyestuffs for fluorescent collectors," Dyes Pigm. 11, 303-317 (1989).
[CrossRef]

M. S. Mackey and W. N. Sisk, "Photostability of pyrromethene 567 laser dye solutions via photoluminescence measurements," Dyes Pigm. 51, 79-85 (2001).
[CrossRef]

J. Photochem. Photobiol. (5)

S. Icli, S. Demic, B. Dindar, A. O. Doroshenko, and C. Timur, "Photophysical and photochemical properties of a water-soluble perylene di-imide derivative," J. Photochem. Photobiol. , A 136, 15-24 (2000).
[CrossRef]

H. Dincalp and S. Icli, "Photosynthesis of rose oxide by concentrated sunlight in the absence of singlet oxygen," J. Photochem. Photobiol. , A 141, 147-151 (2001).
[CrossRef]

W. N. Sisk and W. Sanders, "The concentration dependence of the normalized photostability of 1,3,5,7,8-pentamethyl-2,6-di-t-butylpyrromethene-difluoroborate complex (PM597) methanol solutions," J. Photochem. Photobiol. , A 167, 185-189 (2004).
[CrossRef]

A. A. Gorman, I. Hamblett, T. A. King, and M. D. Rahn, "A pulse radiolysis and pulsed laser study of the pyrromethene 567 triplet state," J. Photochem. Photobiol. , A 130, 127-132 (2000).
[CrossRef]

N. Tanaka and W. N. Sisk, "The photodegradation of pyrromethene 567 and pyrromethene 597 by pyrromethene 546," J. Photochem. Photobiol. , A 172, 109-114 (2005).
[CrossRef]

J. Phys. Chem. A (2)

D. Gosztola, M. P. Niemczyk, W. Svec, A. S. Lukasand, and M. R. Wasielewski, "Excited Doublet States of Electrochemically Generated Aromatic Imide and Di-imide Radical Anions," J. Phys. Chem. A 104, 6545-6551 (2000).
[CrossRef]

L. Chen, L. A. Lucia, E. R. Gaillard, H. Icil, S. Icli, and D. G. Whitten, "Photo-oxidation of a conjugated diene by an exciplex mechanism: amplification via radical chain reactions in the perylene di-imide-photosensitized oxidation of α-terpinene," J. Phys. Chem. A 102, 9095-9098 (1998).
[CrossRef]

J. Phys. Chem. Ref. Data (1)

F. Wilkinson, P. Helman, and A. B. Ross, "Rate constants for the decay and reactions of the lowest electronically excited singlet state of molecular oxygen in solution. An expanded and revised compilation," J. Phys. Chem. Ref. Data 24, 663-1021 (1995).
[CrossRef]

Opt. Commun. (1)

P. Schlup, G. W. Baxter, and I. T. McKinnie, "Single-mode visible and mid-infrared periodically poled lithium niobate optical parametric oscillator amplified in perylene red doped poly(methyl methacrylate)," Opt. Commun. 184, 225-230 (2000).
[CrossRef]

Opt. Mater. (1)

Y. Yang, M. Wang, G. Qian, Z. Wang, and X. Fan, "Laser properties and photostabilities of laser dyes doped in ORMOSILs," Opt. Mater. 24, 621-628 (2004).
[CrossRef]

Opti. Commun. (1)

T. Nhung, M. Canva, F. Chaput, H. Goudket, G. Roger, A. Brun, D. Manh, N. Hung, and J. Boilot, "Dye energy transfer in xerogel matrices and application to solid-state dye lasers," Opti. Commun. 232, 343-351 (2004).
[CrossRef]

Synth. Met. (3)

P. L. Rendu, T. P. Nguyen, and L. Carrois, "Cellulose acetate and PVDC used as protective layers for organic diodes," Synth. Met. 138, 285-288 (2003).
[CrossRef]

K. Ocka, N. Job, J. Kim, S. Kim, and K. Koh, "Thin film optical waveguide type UV sensor using a photochromic molecular device, spirooxazine," Synth. Met. 117, 131-133 (2001).
[CrossRef]

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

Thin Solid Films (1)

G. H. Kim, J. Oh, Y. S. Yang, L. Do, and K. S. Suh, "Lamination process encapsulation for longevity of plastic-based organic light-emitting devices," Thin Solid Films 467, 1-3 (2004).
[CrossRef]

Other (5)

G. S. Egerton and A. G. Morgan, "Photochemistry of dyes. I. Fundamental principles," (J. Soc. Dyers Colour. 86, 79-831970).

G. Jones II, O. Klueva, S. Kumar, and D. Pacheco, "Photochemical and lasing properties of pyrromethene dyes," in Solid State Lasers X, RichardScheps, ed., Proc. SPIE 4267, 24-35 (2001).

R. T. Morrison and R. N. Boyd, Organic Chemistry, 5th ed. (Allyn and Bacon, 1987).

N. N. Barashkov and O. A. Gunder, Fluorescent Polymers (Ellis Horwood, 1994).

M. Tasaki, A. Ichikawa, T. Odaki, and K. Takagi, "Transparent coating member for light-emitting diodes and a fluorescent color light source," U.S. patent 6,319,425, (20 November 2001).

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Figures (9)

Fig. 1
Fig. 1

Generic perylene di-imide dye structure. R represents a phenoxy group (O–C6H5) and H represents Perylene Red and Perylene Orange, respectively.

Fig. 2
Fig. 2

Thin-film sample holder (a) O-ring, (b) thin film, (c) glass slide, (d) O-ring joint, (e) O-ring joint, (f) stopcock.

Fig. 3
Fig. 3

Normalized fluorescence following 532 nm irradiation for samples under ambient conditions (□) and vacuum (○). (●) designates the normalized fluorescence for samples exposed to ambient atmosphere for 5 min with no irradiation following irradiation under vacuum. (a) 2.5 × 10−4 M Lumogen F Red 300–polyester (100 mJ cm−2 pulse−1, 2 Hz) λobs = 643 nm (b) 7.62 × 10−3 M Lumogen F Orange 240–polyester (86 mJ cm−2 pulse−1, 2 Hz) λobs = 587 nm.

Fig. 4
Fig. 4

Normalized fluorescence following 532 nm irradiation for samples under ambient conditions (□) and vacuum (○). (●) designates the normalized fluorescence for samples exposed to ambient atmosphere for 5, 10, 15, and 20 min with no irradiation following irradiation under vacuum. (a) 1.2 × 10−3 M Perylene Red∕PMMA (124 mJ cm−2 pulse−1, 10 Hz) λobs = 602 nm (b) 1.2 × 10−3 M Perylene Orange∕PMMA (169 mJ cm−2 pulse−1, 10 Hz) λobs = 595 nm.

Fig. 5
Fig. 5

Normalized fluorescence following 532 nm irradiation for samples under O2 and vacuum: (●), 10 Torr O2 (○), 50 Torr O2 (□) (Perylene Red), 30 Torr O2 (□) (Perylene Orange), and 150 Torr O2 (Δ). (a) 1.2 × 10−3 M Perylene Red–PMMA (157 mJ cm−2 pulse−1, 10 Hz) λobs = 615 nm, (b) 1.2 × 10−3 M Perylene Orange–PMMA (159 mJ cm−2 pulse−1, 10 Hz) λobs = 583 nm.

Fig. 6
Fig. 6

Normalized absorbance at 578 nm following 532 nm irradiation (138 mJ cm−2 pulse−1) of 3.33 × 10−5 M Perylene Red ethanol solutions devoid of NaN3 (□) and with 3.33 × 10−4 M NaN3 (○) (a) under ambient conditions and (b) under vacuum. ● designates the normalized absorbance for samples exposed to ambient atmosphere for 0, 1, 2, and 3 min following irradiation under vacuum. ■ designates the normalized absorbance for samples exposed to ambient atmosphere for 1.5, 2.3, 3.3, 4.3, and 5.3 min following irradiation under vacuum.

Fig. 7
Fig. 7

Absorbance spectra of 1.67 × 10−5 M Perylene Red∕3.33 × 10−4 M NaN3 in ethanol: Solid curve, initial spectrum under vacuum; dashed curve, following 6000 pulses 532 nm irradiation (138 mJ cm−2 pulse−1) under vacuum; dotted curve, exposure of the 6000 pulse irradiated sample to the ambient atmosphere.

Fig. 8
Fig. 8

Time-resolved 1O2 phosphorescence following 532 nm 1.06 mJ cm−2 pulse−1 irradiation of 2.1 × 10−5 M Perylene Red in benzene. The solid curve represents the least-squares fit for a selected region of the phosphorescence decay profile following a 20 μs delay.

Fig. 9
Fig. 9

Initial 1O2 phosphorescence intensity versus absorbance for C60∕benzene (○) and Perylene Red∕benzene (□). The dashed curve represents the least-squares fit.

Tables (1)

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Table 1 Film Composition and Thickness

Equations (14)

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D h ν D 1 * D 3 ,
D 3 + X D + X .
O 2 + D O 2 + D ,
O 2 + N 3 O 2 + N 3 .
D + h ν k 5 D 1 * ,
D 1 * k 6 D ( + h ν ) ,
D 1 * k 7 D 3 ,
D 3 + N 3 - k 8 D + N 3 - ,
D 3 + O 3 2 k 9 D + O 1 2 ,
O 1 2 + N 3 - k 10 O 3 2 + N 3 - ,
O 1 2 + D k 11 products ,
O 1 2 + D k 12 O 3 2 + D ,
O 1 2 k 13 O 3 2 ( + h ν ) .
phosphorescence intensity = c 0 + c 1 exp ( c 2 t ) .

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