Optical and time-resolved electron paramagnetic resonance studies of the excited states of a UV-B absorber (4-methylbenzylidene)camphor

Journal of Physical Chemistry A

Volumn 117, Issue 7, 2013, Pages 1413-1419

  Kikuchi, Azusa ^a   Shibata, Kenji ^a   Kumasaka, Ryo ^a   Yagi, Mikio ^a  

^a YOKOHAMA NATIONAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DEACTIVATION PROCESS; INTER-SYSTEM CROSSINGS; LUMINESCENCE MEASUREMENTS; MEASUREMENTS OF; NEAR-IR; PHOTO-STABILITY; SINGLET OXYGEN PRODUCTION; TIME-RESOLVED; TIME-RESOLVED ELECTRON PARAMAGNETIC RESONANCES; TIME-RESOLVED EPR; UV ABSORPTION; ZERO-FIELD SPLITTING PARAMETERS;

ACETONITRILE; CAMPHOR; ETHANOL; LIGHT EMISSION; PARAMAGNETISM; PHOSPHORESCENCE; QUANTUM YIELD;

EXCITED STATES;

EID: 84874186728     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp3071772     Document Type: Article

References (58)

1. United Nations Environment Programme Environmental Effects Assessment Panel, Environmental Effects of Ozone Depletion and its Interactions with Climate Change: Progress Report, 2011 Photochem. Photobiol. Sci. 2012, 11, 13-27
2. Attard, N. R.; Karran, P. UVA Photosensitization of Thiopurines and Skin Cancer in Organ Transplant Recipients Photochem. Photobiol. Sci. 2012, 11, 62-68
3. Fourtanier, A.; Moyal, D.; Seite, S. UVA Filters in Sun-Protection Products: Regulatory and Biological Aspects Photochem. Photobiol. Sci. 2012, 11, 81-89
4. Pfeifer, G. P.; Besaratinia, A. UV Wavelength-Dependent DNA Damage and Human Non-Melanoma and Melanoma Skin Cancer Photochem. Photobiol. Sci. 2012, 11, 90-97
5. Mouret, S.; Forestier, A.; Douki, T. The Specificity of UVA-Indused DNA Damage in Human Melanocytes Photochem. Photobiol. Sci. 2012, 11, 155-162
6. Matsumura, Y.; Ananthaswamy, H. N. Toxic Effects of Ultraviolet Radiation on the Skin Toxicol. Appl. Pharmacol. 2004, 195, 298-308
7. Steinberg, D. C. Regulations of Sunscreens Worldwide. Sunscreens; Shaath, N. A., Ed.; Taylor & Francis: Boca Raton, FL, 2005, pp 173-198.
8. Osterwalder, U.; Herzog, B. The Long Way Towards the Ideal Sunscreen-Where We Stand and What Still Needs to Be Done Photochem. Photobiol. Sci. 2010, 9, 470-481
9. Shaath, N. A. The Chemistry of Ultraviolet Filters. Sunscreens; Shaath, N. A., Ed.; Taylor & Francis: Boca Raton, FL, 2005, pp 217-238.
10. Kockler, J.; Oelgemöller, M.; Robertson, S.; Glass, B. D. Photostability of Sunscreens J. Photochem. Photobiol. C 2012, 13, 91-110
11. Shaath, N. A. Ultraviolet Filters Photochem. Photobiol. Sci. 2010, 9, 464-469
12. Bonda, C. A. The Photostability of Organic Sunscreen Actives: a Review. Sunscreens; Shaath, N. A., Ed.; Taylor & Francis: Boca Raton, FL, 2005, pp 321-349.
13. Lhiaubet-Vallet, V.; Marin, M.; Jimenez, O.; Gorchs, C.; Trullas, C.; Miranda, M. A. Filter-Filter Interactions. Photostabilization, Triplet Quenching and Reactivity with Singlet Oxygen Photochem. Photobiol. Sci. 2010, 9, 552-558
14. Kikuchi, A.; Yagi, M. Direct Observation of the Intermolecular Triplet-Triplet Energy Transfer from UV-A Absorber 4- tert -Butyl-4′- Methoxydibenzoylmethane to UV-B Absorber Octyl Methoxycinnamate Chem. Phys. Lett. 2011, 513, 63-66
15. Scalia, S.; Mezzena, M. Photostabilization Effect of Quercetin on the UV Filter Combination, Butyl Methoxydibenzoylmethane-Octyl Methoxycinnamate Photochem. Photobiol. 2010, 86, 273-278
16. Bonda, C. A.; Pavlovic, A.; Hanson, K.; Bardeen, C. Singlet Quenching Proves Faster Is Better for Photostability Cosmet. Toiletries 2010, 125, 40-48
17. Mendrok-Edinger, C.; Smith, K.; Janssen, A.; Vollhardt, J. The Quest for Avobenzone Stabilizers and Sunscreen Photostability Cosmet. Toiletries 2009, 124, 47-54
18. Herzog, B.; Wehrle, M.; Quass, K. Photostability of UV Absorber Systems in Sunscreens Photochem. Photobiol. 2009, 85, 869-878
19. Damiani, E.; Baschong, W.; Greci, L. UV-Filter Combinations under UV-A Exposure: Concomitant Quantification of Over-All Spectral Stability and Molecular Integrity J. Photochem. Photobiol. B 2007, 87, 95-104
20. Damiani, E.; Rosati, L.; Castagna, R.; Carloni, P.; Greci, L. Changes in Ultraviolet Absorbance and Hence in Protective Efficacy against Lipid Peroxidation of Organic Sunscreens after UVA Irradiation J. Photochem. Photobiol. B 2006, 82, 204-213
21. Dondi, D.; Albini, A.; Serpone, N. Interactions between Different Solar UVB/UVA Filters Contained in Commercial Suncreams and Consequent Loss of UV Protection Photochem. Photobiol. Sci. 2006, 5, 835-843
22. Kikuchi, A.; Saito, H.; Mori, M.; Yagi, M. Photoexcited Triplet States of New UV Absorbers, Cinnamic Acid 2-Methylphenyl Esters Photochem. Photobiol. Sci. 2011, 10, 1902-1909
23. Kikuchi, A.; Yukimaru, S.; Oguchi, N.; Miyazawa, K.; Yagi, M. Excited Triplet State of a UV-B Absorber, Octyl Methoxycinnamate Chem. Lett. 2010, 39, 633-635
24. Kikuchi, A.; Oguchi, N.; Yagi, M. Optical and Electron Paramagnetic Resonance Studies of the Excited States of 4- tert -Butyl-4′- Methoxydibenzoylmethane and 4- tert -Butyl-4′-Methoxydibenzoylpropane J. Phys. Chem. A 2009, 113, 13492-13497
25. Kikuchi, A.; Yagi, M. Excited Triplet State of a UV-B Absorber, Octyl Methoxycinnamate Chem. Lett. 2009, 38, 770-771
26. Paris, C.; Lhiaubet-Vallet, V.; Jiménez, O.; Trullas, C.; Miranda, M. á. A Blocked Diketo Form of Avobenzone: Photostability, Photosensitizing Properties and Triplet Quenching by a Triazine-Derived UVB-Filter Photochem. Photobiol. 2009, 85, 178-184
27. Mturi, G. J.; Martincigh, B. S. Photostability of the Sunscreening Agent 4- tert -Butyl-4′-Methoxydibenzoylmethane (Avobenzone) in Solvents of Different Polarity and Proticity J. Photochem. Photobiol. A 2008, 200, 410-420
28. Buser, H.-R.; Müller, M. D.; Balmer, M. E.; Poiger, T.; Buerge, I. J. Stereoisomer Composition of the Chiral UV Filter 4-Methylbenzylidene Camphor in Environmental Samples Environ, Sci. Technol. 2005, 39, 3013-3019
29. Moneyron, H.; Arnaud, R.; Lemaire, J.; Deflandre, A.; Goetz, M. Photochemical E-Z Isomerization of Some Benzylidene Camphor and Benzylidene Tetrahydrofuranone Derivatives J. Photochem. Photobiol. A 1993, 75, 77-82
30. Deflandre, A.; Lang, G. Photostability Assessment of Sunscreens. Benzylidene Camphor and Dibenzoylmethane Derivatives Int. J. Cosmet. Sci. 1988, 10, 53-62
31. Beck, I.; Deflandre, A.; Lang, G.; Arnaud, R.; Lemaire, J. Study of the Photochemical Behaviour of sunscreens-Benzylidene Camphor and Derivatives II: Photosensitized Isomerization by Aromatic Ketones and Deactivation of the 8-Methoxypsoralen Triplet State J. Photochem. 1985, 30, 215-227
32. Beck, I.; Deflandre, A.; Lang, G.; Arnaud, R.; Lemaire, J. Study of the Photochemical Behaviour of Sunscreens-Benzylidene Camphor and Derivatives Int. J. Cosmet. Sci. 1981, 3, 139-152
33. Hauri, U.; Lütolf, B.; Schlegel, U.; Hohl, C. Determination of Photodegradation of UV Filters in Sunscreens by HPLC/DAD and HPLC/MS Mitt. Lebensm. Hyg. 2004, 95, 147-161
34. Gasper, L. R.; Campos, P. M. B. G. M. Photostability and Efficacy Studies of Topical Formulations Containing UV-Filters Combination and Vitamins A, C and E Int. J. Pharm. 2006, 307, 123-128
35. Chatelain, E.; Gabard, B. Photostabilization of Butyl Methoxydibenzoylmethane (Avobenzone) and Ethylhexyl Methoxycinnamate by bis-Ethylhexyloxyphenol Methoxyphenyl Triazine (Tinosorb S), a New UV Broadband Filter Photochem. Photobiol. 2001, 74, 401-406
36. Tarras-Wahlberg, N.; Stenhagen, G.; Larkö, O.; Rosén, A.; Wennberg, A.-M.; Wennerström, O. Changes in Ultraviolet Absorption of Sunscreens after Ultraviolet Irradiation J. Invest. Dermatol. 1999, 113, 547-553
37. Grabowski, Z. R.; Grabowska, A. The Förster Cycle Reconsidered. Z Phys. Chem. (Neue Folge) 1976, 101, 197-208
38. Turro, N. J.; Ramamurthy, V.; Scaiano, J. C. Modern Molecular Photochemistry of Organic Molecules; University Science Books: Sausalito, CA, 2010.
39. Montalti, M.; Credi, A.; Prodi, L.; Gandolfi, M. T. Handbook of Photochemistry, 3 rd ed.; Tayler & Francis: Boca Raton, FL, 2006.
40. 2 J. Phys. Chem. 1996, 100, 8049-8052
41. g) Sensitization J. Photochem. Photobiol. A 1994, 79, 11-17
42. Oliveros, E.; Suardi-Murasecco, P.; Aminian-Saghafi, T.; Braun, A. M. 1 H -Phenalen-1-one: Photophysical Properties and Singlet-Oxygen Production Helv. Chim. Acta 1991, 74, 79-90
43. Yagi, M.; Yamamoto, I.; Sasase, R.; Seki, K. Optical and Time-Resolved Paramagnetic Resonance Studies of the Excited States of Para-Methylcinnamic Acid and Para-Methylcinnamate Anion Appl. Magn. Reson. 2003, 23, 421-434
44. Kottis, P.; Lefebvre, R. Calculation of the Electron Spin Resonance Line Shape of Randomly Oriented Molecules in a Triplet State. I. The Δ m = 2 Transition with a Constant Linewidth J. Chem. Phys. 1963, 39, 393-403
45. Shioya, Y.; Yagi, M. Time-Resolved Electron Paramagnetic Resonance Study of the Lowest Excited Triplet State of trans -Cinnamic Acid J. Photochem. Photobiol. A 1995, 86, 97-102
46. Kottis, P.; Lefebvre, R. Calculation of the Electron Spin Resonance Line Shape of Randomly Oriented Molecules in a Triplet State. II. Correlation of the Spectrum with the Zero-Field Splittings. Introduction of an Orientation- Dependent Linewidth J. Chem. Phys. 1964, 41, 379-393
47. Vergragt, P. J.; van der Waals, J. H. The Lowest Triplet State of Toluene by Microwave Induced Delayed Phosphorescence Chem. Phys. Lett. 1974, 26, 305-311
48. Raynes, W. T. Spin Splittings and Rotational Structure of Nonlinear Molecules in Doublet and Triplet Electronic States J. Chem. Phys. 1964, 41, 3020-3032
49. Boorstein, S. A.; Gouterman, M. Theory for Zero-Field Splittings in Aromatic Hydrocarbons. III J. Chem. Phys. 1963, 39, 2443-2452
50. Oguchi-Fujiyama, N.; Miyazawa, K.; Kikuchi, A.; Yagi, M. Photophysical Properties of Dioctyl 4-Methoxybenzylidenemalonate: UV-B Absorber Photochem. Photobiol. Sci. 2012, 11, 1528-1535
51. Kikuchi, A.; Shibata, K.; Kumasaka, R.; Yagi, M. Excited States of Menthyl Anthranilate: a UV-A Absorber. Photochem. Photobiol. Sci. 2013, 12, 246-253.
52. Kikuchi, A.; Hata, Y.; Kumasaka, R.; Nanbu, Y.; Yagi, M. Photoexcited Singlet and Triplet States of a UV Absorber Ethylhexyl Methoxycrylene. Photochem. Photobiol. DOI: 10.1111/php.12017.
53. Kinoshita, M.; Iwasaki, N.; Nishi, N. Molecular Spectroscopy of the Triplet State through Optical Detection of Zero-Field Magnetic Resonance Appl. Spectrosc. Rev. 1981, 17, 1-94
54. Ikeyama, T.; Azumi, T. Vibrational Analysis of the Phosphorescence of a trans -Stilbene Single Crystal. Is the Phosphorescent State Twisted? J. Phys. Chem. 1994, 98, 2832-2835
55. 3ππ* Aromatic Carbonyls Mol. Phys. 1976, 31, 663-680
56. Karpkird, T. M.; Wanichweacharungruang, S.; Albinsson, B. Photophysical Characterization of Cinnamates Photochem. Photobiol. Sci. 2009, 8, 1455-1460
57. 3 and o -Hydroxybenzophenone in Aqueous Solution J. Phys. Chem. A 1997, 101, 650-655
58. Chudoba, C.; Riedle, E.; Pfeiffer, M.; Elsaesser, T. Vibrational Coherence in Ultrafast Excited State Proton Transfer Chem. Phys. Lett. 1996, 263, 622-628