Micellar control of the photooxidation pathways of 10-methyl phenothiazine: Electron versus energy transfer mechanisms

Photochemical and Photobiological Sciences

Volumn 13, Issue 2, 2014, Pages 281-292

  Manju, Thankamoniamma ^a   Manoj, Narayanapillai ^b   Gejo, Juan López ^c,f   Braun, André M ^d   Oliveros, Esther ^e  

^a Sree Sankara College   (India)

^b Department of Physics   (India)

^c Columbia University 3000 Broadway ^*  (United States)

^d KARLSRUHE INSTITUTE OF TECHNOLOGY   (Germany)

^e Université Paul Sabatier   (France)

^f Mühlbauer High Tech International   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84893124955     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/c3pp50261a     Document Type: Article

References (54)

1. G. Taurand, Phenothiazine and Derivatives, in Ullmann's Encyclopedia of Industrial Chemistry, Wiley, Weinheim, 2000
2. C. O. Okafor New phenothiazine dyes and pigments Dyes Pigm. 1985 6 405 415
3. H. O. Strange J. J. McGrath J. P. Pellegrini Jr. Improved phenothiazine antioxidants for synthetic lubricants Ind. Eng. Chem. Prod. Res. Dev. 1967 6 33 35
4. Q. Chi S. Dong Electrocatalytic oxidation of reduced nicotinalide coenzymes at methylene-green modified electrodes and fabrication of amperometric alcohol biosensors Anal. Chim. Acta 1994 285 125 133
5. M. Lucarini P. Pedrielli G. F. Pedulli L. Valgimigli D. Gigmes P. Tordo Bond dissociation energy of the N-H bond and rate constants for the reaction with alkyl, alkoxyl and peroxyl radicals of phenothiazines and related compounds J. Am. Chem. Soc. 1999 121 11546 11553
6. Phenothiazines and 1,4-benzothiazines: Chemical and Biomedical Aspects, ed., R. R. Gupta, Elsevier, Amsterdam, 1988
7. W. O. Foye, T. L. Lemke and D. A. Williams, in Principles of Medicinal Chemistry, Williams & Wilkins, Baltimore, 4th edn, 1995, ch. 12, p. 205
8. E. Usdin, H. Eckert and I. S. Forrest, Developments in Neuroscience, Elsevier, Amsterdam, 1980, vol. 7
9. B. D. Glass, M. E. Brown and P. M. Drummond, Photoreactivity versus activity of a selected class of phenothiazines: a comparative study, in Drugs: Photochemistry and Photostability, ed., A. Albini, and, E. Fassani, Royal Society of Chemistry, Cambridge, UK, 1998, pp. 134-149
10. J. H. Epstein Photoallergy: A review Arch. Dermatol. 1972 106 741 748
11. N. J. Bunce Y. Kumar L. Ravanal Phototoxicity of chlorpromazine J. Med. Chem. 1979 22 202 204
12. C. F. Chignell A. G. Motten G. R. Buettner Photoinduced free radicals from chlorpromazine and related phenothiazines: relationship to phenothiazine induced photosensitization Environ. Health Perspect. 1985 64 103 110
13. F. Bosca P. Morlière M. A. Miranda J. V. Castell R. Santus Primary steps of the photochemical reactions of 2-cyano-10-(3-[dimethylamino, N-oxide]-2-methylpropyl)-5-oxide-phenothiazine, the photoproduct of cyamemazine, a phototoxic neuroleptic: comparison with the sulfoxide Photochem. Photobiol. Sci. 2006 5 336 342
14. G. Miolo L. Levorato F. Gallocchio S. Caffieri C. Bastianon R. Zanoni E. Reddi In vitro phototoxicity of phenothiazines: involvement of stable UV-A photolysis products formed in aqueous medium Chem. Res. Toxicol. 2006 19 156 163
15. C. García L. Pinero R. Oyola R. Arce Photodegradation of 2-chloro substituted phenothiazines in alcohols Photochem. Photobiol. 2009 85 160 170
16. M. Barra G. S. Calabrese M. T. Allen R. W. Redmond R. Sinta A. A. Lamola R. D. Small J. C. Scaiano Photophysical and photochemical studies of phenothiazine and some derivatives: exploratory studies of novel photosensitizers for photoresist technology Chem. Mater. 1991 3 610 616
17. R. Boch B. Mehta T. Connolly T. Durst J. T. Arnason R. W. Redmond J. C. Scaiano Singlet oxygen photosensitizing properties of bithiophene and terthiophene derivatives J. Photochem. Photobiol., A 1996 3 39 47
18. T. Manju N. Manoj A. M. Braun E. Oliveros Self-sensitized photooxidation of N-methyl phenothiazine: acidity control of the competition between electron and energy transfer mechanisms Photochem. Photobiol. Sci. 2012 11 1744 1755
19. E. Pelizzetti Cation radicals of phenothiazines. Part 4. Electron transfer between aquamanganese(III) and N-alkylphenothiazines J. Chem. Soc. Dalton Trans.: Inorg. Chem. 1980 3 484 486
20. S. Nath H. Pal D. K. Palit A. V. Sapre J. P. Mittal Steady-state and time-resolved studies on photoinduced interaction of phenothiazine and 10-methylphenothiazine with chloroalkanes J. Phys. Chem. A 1998 102 5822 5830
21. Y. Moroi A. M. Braun M. Graetzel Light-initiated electron transfer in functional surfactant assemblies. 1. Micelles with transition metal counterions J. Am. Chem. Soc. 1979 101 567 572
22. J. H. Fendler, Membrane Mimetic Chemistry, Wiley-Interscience, New York, 1982
23. Solution Behaviour of Surfactants, ed., K. L. Mittal, and, J. H. Fendler, Plenum Press, New York, 1982, vol. 2
24. T. Dwars E. Paetzold G. Oehme Reactions in micellar systems Angew. Chem., Int. Ed. 2005 44 7174 7199
25. N. J. Turro M. Grätzel A. M. Braun Photophysical and photochemical processes in micellar systems Angew. Chem., Int. Ed. Engl. 1980 19 675 696
26. J. H. Fendler Microemulsions, micelles and vesicles as media for membrane mimetic photochemistry J. Phys. Chem. 1980 84 1485 1491
27. V. Balzani and F. Scandola, in Energy Resources Through Photochemistry and Catalysis, ed., M. Grätzel, Academic Press, New York, 1983
28. K. Kalyanasundaram, Photochemistry in Microheterogeneous Systems, Academic Press, Orlando, FL, 1987
29. E. Oliveros P. Murasecco-Suardi T. Aminian-Saghafi A. M. Braun 1H-Phenalen-1-one: photophysical properties and singlet oxygen production Helv. Chim. Acta 1991 74 79 90
30. G. L. McIntire Micelles in analytical chemistry Crit. Rev. Anal. Chem. 1990 21 257 278
31. A. M. Braun E. Oliveros Applications of singlet oxygen reactions: mechanistic and kinetic investigations Pure Appl. Chem. 1990 62 1467 1476
32. g) photosensitization. Time-resolved photoacoustics and near-IR emission studies J. Photochem. Photobiol., A 1996 97 11 18
33. g) production by pterin derivatives in aqueous solutions Photochem. Photobiol. Sci. 2003 2 245 250
34. g)): Physical quenching and chemical reaction Photochem. Photobiol. 2007 833 526 534
35. g) J. Phys. Chem. 1995 99 3521 3526
36. F. Wilkinson H. P. Helman A. B. Ross Rate constants for the decay and reaction of the lowest electronically excited singlet state of molecular oxygen in solution. An expanded and revised compilation J. Phys. Chem. Ref. Data 1995 24 663 934
37. g)) in micellar media and microemulsions J. Photochem. Photobiol., B 2000 58 94 107
38. A. M. Braun, M. T. Maurette and E. Oliveros, Photochemical Technology, John Wiley & Sons, Chichester, 1991, ch. 2
39. H. J. Kuhn S. E. Braslavsky R. Schmidt Chemical actinometry (IUPAC technical report) Pure Appl. Chem. 2004 76 2105 2146
40. B. Bales M. Almgren Fluorescence quenching of pyrene by copper(II) in sodium dodecyl sulfate micelles. Effect of micelle size as controlled by surfactant concentration J. Phys. Chem. 1995 99 15153 15162
41. J. M. Corkill J. F. Goodman T. Walker Partial molar volumes of surface-active agents in aqueous solution Trans. Faraday Soc. 1967 63 768 772
42. C. Schweitzer R. Schmidt Physical mechanisms of generation and deactivation of singlet oxygen Chem. Rev. 2003 103 1685 1757
43. E. L. Clennan Persulfoxide: key intermediate in reactions of singlet oxygen with sulfides Acc. Chem. Res. 2001 34 875 884
44. G. J. Kavarnos N. J. Turro Photosensitization by reversible electron transfer: theories, experimental evidence and examples Chem. Rev. 1986 86 401 449
45. 2 in acetonitrile as a facile route to amine radical cation generation Chem. Phys. Lett. 2005 413 294 299
46. P. C. Lee M. A. J. Rodgers Singlet molecular-oxygen in micellar systems: distribution equilibria between hydrophobic and hydrophilic compartments Phys. Chem. 1983 87 4894 4898
47. U. C. Yoon P. S. Mariano Mechanistic and synthetic aspects of amine-enone single electron transfer photochemistry Acc. Chem. Res. 1992 25 233 240
48. Advances in Heterocyclic Chemistry, ed., A. R. Katritzky, and, A. J. Boulton, vol. 9, Academic Press, New York, 1968, p. 351
49. D. T. Sawyer J. S. Valentine How super is superoxide? Acc. Chem. Res. 1981 14 393 400
50. B. H. Bielski D. E. Cabelli Highlights in current research involving superoxide and perhydroxyl radicals in aqueous solutions Int. J. Radiat. Biol. 1991 59 291 319
51. K. Okamoto N. Hirota T. Tominaga M. Terazima Translational diffusion of ion radicals created by electron transfer in charged micellar solutions probed by the transient grating method and the Taylor dispersion method J. Phys. Chem. A 2001 105 6586 6593
52. S. A. Alkaitis G. Beck M. Grätzel Laser photoionization of phenothiazine in alcoholic and aqueous micellar solution. Electron transfer from triplet states to metal ion acceptors J. Am. Chem. Soc. 1975 97 5723 5729
53. C. García R. Oyola L. E. Pinero R. Arce J. Silva V. Sanchez Substitution and solvent effects on the photophysical properties of several series of 10-alkylated phenothiazine derivatives J. Phys. Chem. A 2005 109 3360 3371
54. M. C. Hovey Micellar photochemistry. Photooxidation with intra-micellar-generated singlet oxygen J. Am. Chem. Soc. 1982 104 4196 4202