OSA's Digital Library

Applied Optics

Applied Optics


  • Editor: James C. Wyant
  • Vol. 45, Iss. 16 — Jun. 1, 2006
  • pp: 3846–3851

Photodegradation of polymer-dispersed perylene di-imide dyes

Nobuaki Tanaka, Nikolay Barashkov, Jerry Heath, and Wade N. Sisk  »View Author Affiliations

Applied Optics, Vol. 45, Issue 16, pp. 3846-3851 (2006)

View Full Text Article

Enhanced HTML    Acrobat PDF (468 KB)

Browse Journals / Lookup Meetings

Browse by Journal and Year


Lookup Conference Papers

Close Browse Journals / Lookup Meetings

Article Tools



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 O 2 ( a 1 Δ g X 3 g     ) infrared phosphorescence.

© 2006 Optical Society of America

OCIS Codes
(130.0130) Integrated optics : Integrated optics
(130.3130) Integrated optics : Integrated optics materials
(160.2540) Materials : Fluorescent and luminescent materials
(160.3130) Materials : Integrated optics materials
(160.4890) Materials : Organic materials

Original Manuscript: August 23, 2005
Manuscript Accepted: October 11, 2005

Nobuaki Tanaka, Nikolay Barashkov, Jerry Heath, and Wade N. Sisk, "Photodegradation of polymer-dispersed perylene di-imide dyes," Appl. Opt. 45, 3846-3851 (2006)

Sort:  Author  |  Year  |  Journal  |  Reset  


  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]

Cited By

Alert me when this paper is cited

OSA is able to provide readers links to articles that cite this paper by participating in CrossRef's Cited-By Linking service. CrossRef includes content from more than 3000 publishers and societies. In addition to listing OSA journal articles that cite this paper, citing articles from other participating publishers will also be listed.

« Previous Article  |  Next Article »

OSA is a member of CrossRef.

CrossCheck Deposited