Singlet oxygen-induced photodegradation of the polymers and dyes in optical sensing materials and the effect of stabilizers on these processes

Journal of Physical Chemistry A

Volumn 117, Issue 36, 2013, Pages 8873-8882

  Enko, Barbara ^a   Borisov, Sergey M ^a   Regensburger, Johannes ^b   Bäumler, Wolfgang ^b   Gescheidt, Georg ^a   Klimant, Ingo ^a  

^a GRAZ UNIVERSITY OF TECHNOLOGY   (Austria)

^b UNIVERSITY HOSPITAL REGENSBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

OPTICAL OXYGEN SENSORS; OPTICAL SENSING MATERIALS; OXYGEN CONSUMPTION; OXYGEN CONSUMPTION RATE; PHOTO-STABILITY; PHOTON EMISSIONS; STABILIZING AGENTS; WATER SOLUBILITIES;

ESTERS; OXYGEN; POLYSTYRENES;

POLYMERS;

AMINE; COLORING AGENT; OXYGEN; POLYMER; SINGLET OXYGEN;

CHEMISTRY; CONFERENCE PAPER; LIGHT RELATED PHENOMENA; LUMINESCENCE; PHOTOLYSIS; PHOTON;

AMINES; COLORING AGENTS; LUMINESCENT MEASUREMENTS; OPTICAL PROCESSES; OXYGEN; PHOTOLYSIS; PHOTONS; POLYMERS; SINGLET OXYGEN;

EID: 84884312989     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp4046462     Document Type: Conference Paper

References (76)

1. McDonagh, C.; Burke, C. S.; MacCraith, B. D. Optical chemical sensors Chem. Rev. 2008, 108, 400-422
2. Wolfbeis, O. S. Materials for fluorescence-based optical chemical sensors J. Mater. Chem. 2005, 15, 2657-2669
3. Amao, Y. Probes and Polymers for Optical Sensing of Oxygen Microchim. Acta 2003, 143, 1-12
4. Anzenbacher, P.; Liu, Y.-L.; Kozelkova, M. E. Hydrophilic polymer matrices in optical array sensing Curr. Opin. Chem. Biol. 2010, 14, 693-704
5. Carlsson, D. J.; Wiles, D. M. The Photooxidative Degradation of Polypropylene. Part II. Photostabilization Mechanisms J. Macromol. Sci., Rev. Polym. Technol. 1976, 14, 155-192
6. Ranby, B.; Rabek, J. F. Singlet Oxygen Reactions with Organic Compounds & Polymers; Wiley: New York, 1978; p 342.
7. Rabek, J. F. Photodegradation of Polymers: Physical Characteristics and Applications; Springer: Berlin, 1996; p 212.
8. Foote, C. S.; Wexler, J. Singlet Oxygen. A Probable Intermediate in Photosensitized Autoxidations J. Am. Chem. Soc. 1964, 86, 3880-3881
9. Corey, E. J.; Taylor, W. C. A Study of the Peroxidation of Organic Compounds by Externally Generated Singlet Oxygen Molecules J. Am. Chem. Soc. 1964, 86, 3881-3882
10. Rabek, J. F.; RaÌŠnby, B. The Role of Singlet Oxygen in the Photooxidation of Polymers Photochem. Photobiol. 1978, 28, 557-569
11. Pospisil, J.; Nespurek, S.; Pilar, J. Impact of photosensitized oxidation and singlet oxygen on degradation of stabilized polymers Polym. Degrad. Stab. 2008, 93, 1681-1688
12. Egerton, G. S. Action of light on dyes in polymer materials Br. Polym. J. 1971, 3, 63-67
13. Carraway, E. R.; Demas, J. N.; DeGraff, B. A.; Bacon, J. R. Photophysics and photochemistry of oxygen sensors based on luminescent transition-metal complexes Anal. Chem. 1991, 63, 337-342
14. Fuller, Z. J.; Bare, W. D.; Kneas, K. a.; Xu, W. Y.; Demas, J. N.; DeGraff, B. A. Photostability of luminescent ruthenium(II) complexes in polymers and in solution Anal. Chem. 2003, 75, 2670-2677
15. Hartmann, P. Photobleaching of a ruthenium complex in polymers used for oxygen optodes and its inhibition by singlet oxygen quenchers Sens. Actuators, B 1998, 51, 196-202
16. Hartmann, P. Photochemically induced energy-transfer effects on the decay times of ruthenium complexes in polymers Anal. Chem. 2000, 72, 2828-2834
17. Oige, K.; Avarmaa, T.; Suisalu, A.; Jaaniso, R. Effect of long-term aging on oxygen sensitivity of luminescent Pd-tetraphenylporphyrin/PMMA films Sens. Actuators, B 2005, 106, 424-430
18. Wiles, D. M. Stabilization of Polymers Against Singlet Oxygen. In Singlet Oxygen. Reactions with Organic Compounds & Polymers; Ranby, B.; Rabek, J. F., Eds.; Wiley: New York, 1978; pp 320-327.
19. Young, R. H.; Brewer, D. R. The Mechanism of Quenching Singlet Oxygen. In Singlet Oxygen. Reactions with Organic Compounds & Polymers; Ranby, B.; Rabek, J. F., Eds.; Wiley: New York, 1978; pp 36-60.
20. Bellus, D. Qunechers of Singlet Oxygen: A Critical Review. In Singlet Oxygen. Reactions with Organic Compounds & Polymers; Ranby, B.; Rabek, J. F., Eds.; Wiley: New York, 1978; pp 61-110.
21. Ohara, K.; Kikuchi, K.; Origuchi, T.; Nagaoka, S. Singlet oxygen quenching by trolox C in aqueous micelle solutions J. Photochem. Photobiol., B 2009, 97, 132-137
22. He, S.; Jiang, L.; Wu, B.; Pan, Y.; Sun, C. Pallidol, a resveratrol dimer from red wine, is a selective singlet oxygen quencher Biochem. Biophys. Res. Commun. 2009, 379, 283-287
23. Ballardini, R.; Beggiato, G.; Bortolus, P.; Faucitano, A.; Buttafava, A.; Gratani, F. Quenching of Singlet Oxygen by Hindered Amine Light Stabilisers. A Flash Photolytic Study Polym. Degrad. Stab. 1984, 7, 41-53
24. Monroe, B. M. Quenching of singlet oxygen by aliphatic amines J. Phys. Chem. 1977, 81, 1861-1864
25. 2) by cubane and its derivatives Org. Lett. 2008, 10, 5509-5512
26. Das, K. C.; Misra, H. P. Hydroxyl radical scavenging and singlet oxygen quenching properties of polyamines Mol. Cell. Biochem. 2004, 262, 127-133
27. Nagaoka, S.; Fujii, A.; Hino, M.; Takemoto, M.; Yasuda, M.; Mishima, M.; Ohara, K.; Masumoto, A.; Uno, H.; Nagashima, U. UV protection and singlet oxygen quenching activity of aloesaponarin I J. Phys. Chem. B 2007, 111, 13116-13123
28. Jung, M. Y.; Min, D. B. ESR study of the singlet oxygen quenching and protective activity of Trolox on the photodecomposition of riboflavin and lumiflavin in aqueous buffer solutions J. Food Sci. 2009, 74, C449-C455
29. Ouannes, C.; Wilson, T. Quenching of singlet oxygen by tertiary aliphatic amines. Effect of DABCO (1,4-diazabicyclo[2.2.2]octane) J. Am. Chem. Soc. 1968, 90, 6527-6528
30. Vieyra, F. E. M.; Boggetti, H. J.; Zampini, I. C.; Ordoñez, R. M.; Isla, M. I.; Alvarez, R. M. S.; De Rosso, V.; Mercadante, A. Z.; Borsarelli, C. D. Singlet oxygen quenching and radical scavenging capacities of structurally-related flavonoids present in Zuccagnia punctata Cav Free Radical Res. 2009, 43, 553-564
31. g) by amines J. Am. Chem. Soc. 1970, 92, 5034-5036
32. Kanofsky, J. R.; Sima, P. D. Quenching of singlet oxygen by a carotenoid-cyclodextrin complex: The importance of aggregate formation Photochem. Photobiol. 2009, 85, 391-399
33. Gutiérrez, M. I. Solvent effect on the physical quenching of singlet molecular oxygen by p-quinones Photochem. Photobiol. Sci. 2008, 7, 480-484
34. Kaiser, S.; Di Mascio, P.; Murphy, M. Physical and Chemical Quenching of Singlet Molecular Oxygen by Tocopherols Arch. Biochem. Biophys. 1990, 277, 101-108
35. Gijsman, P. New synergists for hindered amine light stabilizers Polymer 2002, 43, 1573-1579
36. Regensburger, J.; Maisch, T.; Felgenträger, A.; Santarelli, F.; Bäumler, W. A helpful technology: The luminescence detection of singlet oxygen to investigate photodynamic inactivation of bacteria (PDIB) J. Biophotonics 2010, 3, 319-327
37. Klimant, I.; Kühl, M.; Glud, R. N.; Holst, G. Optical measurement of oxygen and temperature in microscale: Strategies and biological applications Sens. Actuators, B 1997, 38, 29-37
38. Papkovsky, D. B.; Ponomarev, G. V.; Trettnak, W.; O'Leary, P. Phosphorescent Complexes of Porphyrin Ketones: Optical Properties and Application to Oxygen Sensing Anal. Chem. 1995, 67, 4112-4117
39. Lee, S.-K.; Okura, I. Photostable Optical Oxygen Sensing Material: Platinum Tetrakis(pentafluorophenyl)porphyrin Immobilized in Polystyrene Anal. Commun. 1997, 34, 185-188
40. Mills, A.; Lepre, A. Controlling the Response Characteristics of Luminescent Porphyrin Plastic Film Sensors for Oxygen Anal. Chem. 1997, 69, 4653-4659
41. Koren, K.; Borisov, S. M.; Klimant, I. Stable optical oxygen sensing materials based on click-coupling of fluorinated platinum(II) and palladium(II) porphyrins: A convenient way to eliminate dye migration and leaching Sens. Actuators, B 2012, 169, 173-181
42. Borisov, S. M.; Wolfbeis, O. S. Temperature-sensitive europium(III) probes and their use for simultaneous luminescent sensing of temperature and oxygen Anal. Chem. 2006, 78, 5094-5101
43. Stich, M. I. J.; Nagl, S.; Wolfbeis, O. S.; Henne, U.; Schaeferling, M. A Dual Luminescent Sensor Material for Simultaneous Imaging of Pressure and Temperature on Surfaces Adv. Funct. Mater. 2008, 18, 1399-1406
44. Schreml, S.; Meier, R. J.; Wolfbeis, O. S.; Maisch, T.; Szeimies, R.-M.; Landthaler, M.; Regensburger, J.; Santarelli, F.; Klimant, I.; Babilas, P. 2D luminescence imaging of physiological wound oxygenation Exp. Dermatol. 2011, 20, 550-554
45. Mills, A.; Chang, Q. Fluorescence plastic thin-film sensor for carbon dioxide Analyst 1993, 118, 839-843
46. Mills, A.; Chang, Q. Tuning colourimteric and fluorimetric gas sensors for carbon dioxide Anal. Chim. Acta 1994, 285, 113-123
47. 2 in gas phase based on sensing film coating optoelectronic elements Sens. Actuators, B 2010, 144, 232-238
48. Apostolidis, A.; Klimant, I.; Andrzejewski, D.; Wolfbeis, O. S. A combinatorial approach for development of materials for optical sensing of gases ACS Comb. Chem. 2004, 6, 325-331
49. Alentiev, A.; Drioli, E.; Gokzhaev, M.; Golemme, G.; Ilinich, O.; Lapkin, A.; Volkov, V.; Yampolskii, Y. Gas permeation properties of phenylene oxide polymers J. Membr. Sci. 1998, 138, 99-107
50. Mi, Y.; Stern, S. A. Gas permeability of a new silicone ring polymer: Isotactic poly(phenyl silsesquioxane) J. Polym. Sci., Part B: Polym. Phys. 1991, 29, 389-393
51. Klimant, I.; Ruckruh, F.; Liebsch, G.; Stangelmayer, A.; Wolfbeis, O. S. Fast Response Oxygen Micro-Optodes Based on Novel Soluble Ormosil Glasses Microchim. Acta 1999, 131, 35-46
52. 2 sensing probe based on cell-penetrating phosphorescent nanoparticles ACS Nano 2011, 5, 5499-5508
53. Lai, S.-W.; Hou, Y.-J.; Che, C.-M.; Pang, H.-L.; Wong, K.-Y.; Chang, C. K.; Zhu, N. Electronic spectroscopy, photophysical properties, and emission quenching studies of an oxidatively robust perfluorinated platinum porphyrin Inorg. Chem. 2004, 43, 3724-3732
54. Krasnovsky, A. A. Photoluminescence of Singlet Oxygen in Pigment Solutions Photochem. Photobiol. 1979, 29, 29-36
55. Egorov, S. Y.; Kamalov, V. F.; Koroteev, N. I.; Krasnovsky, A. A. J.; Toleutaev, B. N.; Zinukov, S. V. Rise and Decay Kinetics of Photosensitized Singlet Oxygen Luminescence in Water. Measurements with Nanosecond Time-Correlated Single Photon Counting Technique Chem. Phys. Lett. 1989, 163, 421-424
56. Ogilby, P. R.; Foote, C. S. Chemistry of Singlet Oxygen. 36. Singlet Molecular Oxygen Luminescence in Solution following Pulsed Laser Excitation. Solvent Deuterium Isotope Effects on the Lifetime of Singlet Oxygen J. Am. Chem. Soc. 1982, 104, 2069-2070
57. Ogilby, P. R.; Dillon, M. P.; Kristiansen, M.; Clough, R. L. Quenching of singlet oxygen in solid organic polymers Macromolecules 1992, 25, 3399-3405
58. Ogilby, P. R.; Kai Kong, I. The Photosensitized Production of Singlet Molecular Oxygen in a Solid Organic Polymer Glass: A Direct Time-Resolved Study J. Am. Chem. Soc. 1987, 109, 4746-4747
59. Schiller, K.; Müller, F. W. Singlet oxygen lifetime in polymer films Polym. Int. 1991, 25, 19-22
60. Baier, J.; Fuss, T.; Pöllmann, C.; Wiesmann, C.; Pindl, K.; Engl, R.; Baumer, D.; Maier, M.; Landthaler, M.; Bäumler, W. Theoretical and experimental analysis of the luminescence signal of singlet oxygen for different photosensitizers J. Photochem. Photobiol., B 2007, 87, 163-173
61. Rivaton, A.; Gardette, J.-L.; Mailhot, B.; Morlat-Therlas, S. Basic Aspects of Polymer Degradation Macromol. Symp. 2005, 225, 129-146
62. Gugumus, F. Mechanisms of photooxidation of polyolefins Angew. Makromol. Chem. 1990, 176, 27-42
63. Fraïsse, F.; Kumar, A.; Commereuc, S.; Verney, V. Photo-oxidation of polymers: Validation of oxygen uptake and relationship with extent of hydroperoxidation J. Appl. Polym. Sci. 2006, 99, 2238-2244
64. Scheirs, J.; Bigger, S. W.; Billingham, N. C. A review of oxygen uptake techniques for measuring polyolefin oxidation Polym. Test. 1995, 14, 211-241
65. Wilson, J. E. Oxygen Uptake of Polyethylene at Elevated Temperatures Ind. Eng. Chem. 1955, 47, 2201-2205
66. Lloyd, D.; Thomas, K.; Price, D.; O'Neil, B.; Oliver, K.; Williams, T. N. A membrane-inlet mass spectrometer miniprobe for the direct simultaneous measurement of multiple gas species with spatial resolution of 1 mm J. Microbiol. Methods 1996, 25, 145-151
67. Oran, U.; Swaraj, S.; Friedrich, J. F.; Unger, W. E. S. Surface analysis of plasma-deposited polymer films by time of flight static secondary ion mass spectrometry (ToF-SSIMS) before and after exposure to ambient air Surf. Coat. Technol. 2005, 200, 463-467
68. Bigger, S. W.; Delatycki, O. New approach to the measurement of polymer photooxidation J. Polym. Sci., Part A: Polym. Chem. 1987, 25, 3311-3323
69. Ogilby, P. R.; Kristiansen, M.; Mártire, D. O.; Scurlock, R. D.; Taylor, V. L.; Clough Roger, L. Formation and Removal of Singlet Oxygen in Bulk Polymers: Events that May Influence Photodegradation; Clough, R. L.; Billingham, N. C.; Gillen, K. T., Eds.; American Chemical Society: Washington, DC, 1996; Vol. 249, pp 113-126.
70. Labuschagne, P. W.; Germishuizen, W. A.; Verryn, S. M. C.; Moolman, F. S. Improved oxygen barrier performance of poly(vinyl alcohol) films through hydrogen bond complex with poly(methyl vinyl ether-co-maleic acid) Eur. Polym. J. 2008, 44, 2146-2152
71. Stern, S. A.; Shah, V. M.; Hardy, B. J. Structure-permeability relationships in silicone polymers J. Polym. Sci., Part B: Polym. Phys. 1987, 25, 1263-1298
72. Kelleher, P. G.; Gesner, B. D. Oxidation of ether linker thermoplastics Polym. Eng. Sci. 1970, 10, 38-42
73. Nagl, S.; Baleizão, C.; Borisov, S. M.; Schäferling, M.; Berberan-Santos, M. N.; Wolfbeis, O. S. Dual fluorescence sensor for trace oxygen and temperature with unmatched range and sensitivity Angew. Chem., Int. Ed. 2007, 46, 2317-2319
74. Baleizão, C.; Nagl, S.; Schäferling, M.; Berberan-Santos, M. N.; Wolfbeis, O. S. Dual Fluorescence Sensor for Trace Oxygen and Temperature with Unmatched Range and Sensitivity Anal. Chem. 2008, 80, 6449-6457
75. Peeling, J.; Clark, D. T. ESCA study of the surface photo-oxidation of some non-aromatic polymers Polym. Degrad. Stab. 1981, 3, 177-185
76. Young, R. H.; Martin, R. L. Mechanism of quenching of singlet oxygen by amines J. Am. Chem. Soc. 1972, 94, 5183-5185