Ionic liquids as a novel medium for photochemical reactions. Ru(bpy) 32+/viologen in imidazolium ionic liquid as a photocatalytic system mimicking the oxido-reductase enzyme

Photochemistry and Photobiology

Volumn 82, Issue 1, 2006, Pages 185-190

  Álvaro, Mercedes ^a   Carbonell, Esther ^a   Ferrer, Belen ^a   Garcia, Hermenegildo ^a   Herance, José R ^b  

^a UNIVERSITAT POLITÈCNICA DE VALÈNCIA   (Spain)

^b UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2,2' BIPYRIDINE; BIS(BIPYRIDYL)RUTHENIUM(II); DRUG DERIVATIVE; IMIDAZOLE DERIVATIVE; ORGANOMETALLIC COMPOUND; OXIDOREDUCTASE; RUTHENIUM; VIOLOGEN;

BIOLOGICAL MODEL; CATALYSIS; CHEMISTRY; CONFERENCE PAPER; METABOLISM; METHODOLOGY; PHOTOCHEMISTRY;

2,2'-DIPYRIDYL; CATALYSIS; IMIDAZOLES; MODELS, BIOLOGICAL; ORGANOMETALLIC COMPOUNDS; OXIDOREDUCTASES; PHOTOCHEMISTRY; RUTHENIUM; VIOLOGENS;

EID: 33644746542     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1562/2005-05-25-RA-542     Document Type: Conference Paper

References (37)

1. Weiner, H., E. Maser, T. D. Hurley and R. Lindahl (eds.) (2001) Proceedings of the Tenth Conference on Enzymology and Molecular Biology of Carbonyl Metabolism, pp. 980-982. Elsevier, Shanon, Ireland
2. + models for tandem cofactor regeneration, horse liver alcohol dehydrogenase recognition of 1,4-NADH derivatives, and chiral synthesis. Angew. Chem. Int. Ed. 41, 478-481.
3. Kiwi, J. (1981) Photochemical generation of reduced b-nicotinamide- adenine dinucleotide (induced by visible light). J. Photochem. 16, 193-202.
4. Wienkamp, R. and E. Steckhan (1983) Selective production of NADH by visible light. Angew. Chem. 95, 508-509.
5. Fukuzumi, S., S. Koumitsu, K. Hironaka and T. Tanaka (1987) Energetic comparison between photoinduced electron-transfer reactions from NADH model compounds to organic and inorganic oxidants and hydride-transfer reactions from NADH model compounds to p-benzoquinone derivatives. J. Am. Chem. Soc. 109, 305-316.
6. Fukuzumi, S., O. Inada and T. Suenobu (2003) Mechanisms of electron-transfer oxidation of NADH analogues and chemiluminescence. Detection of the keto and enol radical cations. J. Am. Chem. Soc. 125, 4808-4816.
7. 2+ (bpy = 2,2′-bipyridine) in water/DMF. Chem. Lett. 2, 339-342.
8. Hironaka, K., S. Fukuzumi and T. Tanaka (1984) Tris(bipyridyl) ruthenium(II)-photosensitized reaction of 1-benzyl-1,4-dihydronicotinamide with benzyl bromide. J. Chem. Soc. Perkin Trans. 2 10, 1705-1709.
9. 2+. J. Org. Chem. 48, 2941-2942.
10. Ishitani, O., M. Ihama, Y. Miyauchi and C. Pac (1985) Redox-photosensitized reactions. Part 12. Effects of magnesium(II) ion on the tris(2,2′-bipyridine)ruthenium(2+)-photomediated reduction of olefins by 1-benzyl-1,4-dihydronicotinamide: metal-ion catalysis of electron transfer processes involving an NADH model. J. Chem. Soc. Perkin Trans. 1 7, 1527-1531.
11. Ishitani, O., S. Yanagida, S. Takamuku and C. Pac (1987) Redox-photosensitized reactions. XIV. Photochemistry of 4-alkylated NADH models, 1-benzyl-4-(1-hydroxyalkyl)-1,4-dihydronicotinamides. Bull. Chem. Soc. Jpn. 60, 1801-1805.
12. 2+-photosensitized reactions of 1-benzyl-1,4-dihydronicotinamide with aryl-substituted enones, derivatives of methyl cinnamate, and substituted cinnamonitriles: electron-transfer mechanism and structure-reactivity relationships. J. Org. Chem. 49, 26-34.
13. Corma, A. and H. Garcia (2004) Zeolite-based photocatalysts. Chem. Commun. 1443-1459.
14. Welton, T. (1999) Room-temperature ionic liquids. Solvents for synthesis and catalysis. Chem. Rev. 99, 2071-2083.
15. Dupont, J., R. F. de Souza and P. A. Z. Suarez (2002) Ionic liquid (molten salt) phase organometallic catalysis. Chem. Rev. 102, 3667-3691.
16. Kavarnos, G. J. and N. J. Turro (1986) Photosensitization by reversible electron transfer: theories, experimental evidences, and examples. Chem. Rev. 86, 401-449.
17. Pagni, R. M. and C. M. Gordon (2004) Handbook of Organic Photochemistry and Photobiology; 2nd ed. CRC Press, Boca Raton, FL.
18. Carmichael, A. J. and K. R. Seddon (2000) Polarity study of some 1-alkyl-3-methylimidazolium ambient-temperature ionic liquids with the solvatochromic dye, Nile Red. J. Phys. Org. Chem. 13, 591-595.
19. Alvaro, M., B. Ferrer, H. Garcia and M. Narayana (2002) Screening of an ionic liquid as medium for photochemical reactions. Chem. Phys. Lett. 362, 435-440.
20. Gordon, C. M. and A. J. McLean (2000) Photoelectron transfer from excited-state ruthenium (II) tris(bipyridyl) to methylviologen in an ionic liquid. Chem. Commun. 1395-1396.
21. Gilbert, A. and J. Baggott (1990) Essentials of Organic Photochemisry. Blackwell, Oxford, UK.
22. Turro, N. J. (1978) Modern Molecular Photochemistry. Benjamin/Cummings, Menlo Park, CA.
23. McClelland, R. A., C. Chan, F. Cozens, A. Modro and S. Steenken (1991) Laser flash photolysis generation spectra, and lifetimes of phenylcarbenium ions in trifluoroethanol and hexafluoroisopropyl alcohol. On the UV spectrum of the benzyl cation. Angew. Chem. Int. Ed. Engl. 30, 1337-1339.
24. Turro, N. J., X. Lei and C.-C. Cheng (1985) Photolysis of dibenzyl ketones in the presence of pentasil zeolites. Examples of size/shape selectivity and molecular diffusional traffic control. J. Am. Chem. Soc. 107, 5824-5826.
25. Baldovíitor, M. V., F. L. Cozens, V. Fornés, H. García and J. C. Scaiano (1996) Intrazeolite photochemistry. 11. Modification of the properties of the energy transfer photosensitizer 4-aminobenzophenone by immobilization within different zeolite microenvironments. Chem. Mater. 8, 152-160.
26. Wilkinson, F. and G. Kelly (1989) Handbook of Organic Photochemistry. CRC Press. Boca Raton, FL.
27. Kelly, G., C. J. Willsher, F. Wilkinson, J. C. Netto-Ferreira, A. Olea, D. Weir, L. J. Johnston and J. C. Scaiano (1990) Intrazeolite photochemistry. VI. Diffuse reflectance laser flash photolysis and product studies of diphenylmethyl radicals on solid supports. Can. J. Chem. 68, 812-819.
28. Garcia, H. and H. D. Roth (2002) Generation and reactions of organic radical cations in zeolites. Chem. Rev. 102, 3947-4008.
29. 2+ and methylviologen. J. Phys. Chem. 96, 9410-9419.
30. Dutta, P. K. (1995) Zeolite guest-host interactions-implications in formation, catalysis, and photochemistry. J. Incl. Phen. Mol. Recogn. Chem. 21, 215-237.
31. Castagnola, N. and P. K. Dutta (2001) Artificial photosynthesis using zeolites. Stud. Surf. Sci. Catal. 135, 4508-4516.
32. Clennan, E. L. (2004) Viologen embedded zeolites. Coord. Chem. Rev. 248, 477-492.
33. 2+-viologen dyad. Chem. A Eur. J. 8, 102-110.
34. Murov, S. L. (1973) Handbook of Organic Photochemistry. Marcel Dekker, New York.
35. Alvaro, M., A. Corma, B. Ferrer, H. Garcia and E. Palomares (2004) Laser flash photolysis study of anthracene/viologen charge transfer complex in non-polar, dealuminated zeolites. Phys. Chem. Chem. Phys. 6, 1345-1349.
36. Thomas, J. K. (1993) Physical aspects of photochemistry and radiation chemistry of molecules adsorbed on silica, γ-alumina, zeolites, and clays. Chem. Rev. 93, 301-320.
37. Sankararaman, S., K. B. Yoon, T. Yabe and J. K. Kochi (1991) Control of back electron transfer from charge-transfer ion pairs by zeolite supercages. J. Am. Chem. Soc. 113, 1419-1425.