Alkali ion exchanged nafion as a confining medium for photochemical reactions

Photochemistry and Photobiology

Volumn 82, Issue 1, 2006, Pages 139-145

  Arumugam, Selvanathan ^a   Kaanumalle, Lakshmi S ^a   Ramamurthy, V ^a  

^a Department of Biology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33644746544     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1562/2005-05-05-RA-515     Document Type: Conference Paper

References (55)

1. Sheldon, R. A. (1996) Chirotechnology: designing economic chiral synthesis. J. Chem. Technol. Biotechnol. 67, 1-14.
2. Pearce, R. (1978) Catalytic chiral synthesis. Catalysis 2, 176-197.
3. Ariel, S., S. Askari, S. V. Evans, C. Hwang, J. Jay, J. R. Scheffer, J. Trotter, L. Walsh and Y. F. Wong (1987) Reaction selectivity in solid state photochemistry. Tetrahedron 43, 1253-1272.
4. Weiss, R. G., V. Ramamurthy and G. S. Hammond (1993) Photochemistry in organized and confining media: a model. Acc. Chem. Res. 26, 530-536.
5. Ramamurthy, V., D. F. Eaton and J. V. Caspar (1992) Photochemical and photophysical studies of organic molecules included within zeolites. Acc. Chem. Res. 25, 299-307.
6. Ronald, F. and A. G. Mika (1982) Nafion-catalyzed photoreaction. Photoisomerization of 3-methylene-1, 2, 4, 5, 6, 6-hexamethylcyclohexa-1, 3-diene. J. Org. Chem. 47, 4204-4207.
7. Tung, C. H. and J. G. Qu (1996) Modification of photochemical reactivity by Nafion. Photocyclization and photochemical cis-trans isomerization of azobenzene. J. Org. Chem. 61, 9417-9421.
8. Tung, C. H. and J. G. Qu (1998) Regioselectivity in the photocycloaddition of 9-substituted anthracenes incorporated within Nafion membranes. J. Org. Chem. 63, 5857-5862.
9. Tung, C. H. and X. H. Xu (1999) Selectivity in the photo-Fries reaction of phenyl phenylacetates included in a Nafion membrane. Tetrahedron Lett. 40, 127-130.
10. Li, X. H., L. Z. Wu, L. P. Zhang and C. H. Tung (2002) Controlled photocyclization, photodimerization and photoisomerization of stilbazole salts within Nafion membranes. Org. Lett. 4, 1175-1177.
11. 2- mediated oxidation of alkenes based on Nafion-supported platinum (II) terpyridyl acetylide complex. Org. Lett. 5, 3221-3224.
12. Yeager, H. J. and A. Eisenberg (1982) Transport properties of perfluorosulfonate polymer membranes. In Perfluorinated Ionomer Membrane, ACS Symposium Series 180 (Edited by A. Eisenberg and H. L. Yeager), pp. 1-6, 41-63. American Chemical Society, Washington, DC.
13. Mauritz, K. A., C. J. Hora and A. J. Hopfinger (1980) Theoretical model for the structure of ionomer: Application to Nafion materials. In Ions in Polymers, ACS Advances in Chemistry Series 187 (Edited by A. Eisenberg), pp. 124-145. American Chemical Society, Washington, DC.
14. Mauritz, K. A., R. F. Store and C. K. Jones (1989) Perfluorinated ionomer membrane based microcomposites. Silicon oxide filled membranes. In Multiphase Polymer Material, Blends, Ionomers, and Interpenetrating Networks, ACS Symposium Series 395 (Edited by L. A. Utracki and R. A. Weiss), pp. 401-417. American Chemical Society, Washington, DC.
15. Eisenberg, A. and M. King (1977) Ion-Containing Polymers: Physical Properties and Structure. Academic Press, New York.
16. Heitner, W. C. (1983) Ion transport and clustering in Nafion perfluorinated membranes. J. Membr. Sci. 13, 307-26.
17. Gierke, T. D., E. Munn and F. C. Wilson (1981) The morphology in Nafion perfluorinated membrane products, as determined by wide- and small-angle X-ray studies. J. Polym. Sci., Part B: Polym. Phys. 19, 1687-1704.
18. Szentirmay, M. N., N. Prieto and C. R. Martin (1985) Luminescence probe studies of ionomers. 1. Steady state measurements from Nafion membrane. J. Phys. Chem. 89, 3017-3023.
19. Niu, E. P., K. P. Ghihhino, T. A. Smith and A. W. H. Mau (1990) Energy transfer between fluorescent dyes in alcohols and in Nafion membranes. J. Lumin. 46, 191-199.
20. Kaanumalle, L. S., J. Nithyanandhan, M. Pattabiraman, N. Jayaraman and V. Ramamurthy (2004) Water-soluble dendrimers as photochemical reaction media: chemical behavior of singlet and triplet radical pairs inside dendritic reaction cavities. J. Am. Chem. Soc. 126, 8999-9006.
21. Corbin, D. R., D. F. Eaton and V. Ramamurthy (1988) Modification of photochemical reactivity by zeolites: Norrish Type I and Type II reactions of benzoin derivatives. J. Am. Chem. Soc. 110, 4848-4849.
22. Rabjohn, N. (1963) Organic Synthesis. Wiley, New York.
23. Cowan, D. O. and R. L. Drisko (1970) Photochemical reactions. IV. Photodimerization of acenaphthylene. Mechanistic studies. J. Am. Chem. Soc. 92, 6286-6291.
24. Yoshizawa, M., Y. Takeyama, T. Okano and M. Fujita (2003) Cavity-directed synthesis within a self-assembled coordination cage: highly selective [2 + 2] cross-photodimerization of olefins. J. Am. Chem. Soc. 125, 3243-3247.
25. Lee, P. C. and D. Meisel (1985) Photophysical studies of pyrene incorporated in Nafion membrane. Photochem. Photobiol. 41, 21-26.
26. Blatt, E., A. Launikonis, A. W. H. Mau and W. H. F. Sasse (1987) Luminescence probe studies of pyrene and two charged derivatives in Nafion. Aust. J. Chem. 40, 1-12.
27. Weir, D. and J. C. Scaiano (1987) Study of the excited states of Nafion incorporated xanthone and benzophenone. Tetrahedron 43, 1617-1623.
28. Bellus, D. (1971) Photo-Fries rearrangement and related photochemical [1,j]-shifts (j = 3, 5, 7) of carbonyl and sulfonyl groups. Adv. Photochem. 8, 109-159.
29. Bellus, D. and P. Hrdlovic (1967) Photochemical rearrangement of aryl, vinyl, and substituted vinyl esters and amides of carboxylic acids. Chem. Rev. 67, 599-609.
30. Cui, C. and R. G. Weiss (1993) Photo-Fries rearrangements of 2-naphthyl acylates as probes of the size and shape of guest sites afforded by unstretched and stretched low-density polyethylene films. A case of remarkable selectivity. J. Am. Chem. Soc. 115, 9820-9821.
31. Pitchumani, K., M. Warrier and V. Ramamurthy (1996) Remarkable product selectivity during photo-Fries and photo-Claisen rearrangements within Zeolites. J. Am. Chem. Soc. 118, 9428-9429.
32. Miranda, M. A. (1995) Photo-Fries reactions and related processes. In CRC Handbook of Photochemistry and Photobiology (Edited by W. M. Horspool and P. S. Song), pp. 570-578. CRC Press, Boca Raton, FL.
33. Gu, W., M. Warrier, V. Ramamurthy and R. G. Weiss (1999) Photo-Fries reactions of 1-naphthyl esters in cation-exchanged zeolite Y and polyethylene media. J. Am. Chem. Soc. 121, 9467-9468.
34. Gu, W., A. J. Hill, X. Wang, C. Cui and R. G. Weiss (2000) Photorearrangements of five 1- and 2-naphthyl acylates in three unstretched and stretched polyethylene films. Does reaction selectivity correlate with free volumes measured by positron annihilation lifetime spectroscopy? Macromolecules 33, 7801-7811.
35. Gu, W. and R. G. Weiss (2000) Mediation of photochemical reactions of 1-naphthyl phenylacylates by polyolefin films. A 'radical clock' to measure rates of radical-pair cage recombinations in 'viscous space.' Tetrahedron 56, 6913-6925.
36. Gu, W. and R. G. Weiss (2001) Extracting fundamental photochemical and photophysical information from photorearrangements of aryl phenylacylates and aryl benzyl ethers in media comprised of polyolefinic films. J. Photochem. Photobiol. C 2, 117-137.
37. Gu, W. and R. G. Weiss (2002) Photo-Fries rearrangements of phenyl phenylacylates in polyethylene films. Comparison of reactivity and selectivity with 1-naphthyl phenylacylates. J. Org. Chem. 66, 1775-1780.
38. Gu, W., S. Bi and R. G. Weiss (2002) Photo-Fries rearrangements of l-naphthyl esters in the glassy and melted states of poly (vinyl acetate). Comparisons with reactions in less polar polymers and low-viscosity solvents. Photochem. Photobiol. Sci. 1, 52-59.
39. Warrier, M., L. S. Kaanumalle and V. Ramamurthy (2003) Alkali metal ion controlled product selectivity during photorearrangements of 1-naphthyl phenyl acylates and dibenzyl ketones within Zeolites. Can. J. Chem. 81, 620-631.
40. Ramamurthy, V., J. V. Caspar, D. F. Eaton, E. W. Kuo and D. R. Corbin (1992) Heavy-atom-induced phosphorescence of aromatics and olefins included within Zeolites. J. Am. Chem. Soc. 114, 3882-3892.
41. Robbins, W. K. and R. H. Eastman (1970) Photodecarbonylation in solution. I. Quantum yields and quenching results with dibenzyl ketones. J. Am. Chem. Soc. 92, 6076-6077.
42. Engel, P. S. (1970) Photochemistry of dibenzyl ketone. J. Am. Chem. Soc. 92, 6074-6076.
43. Lewis, F. D., R. T. Lauterbach, H. G. Heine, W. Hartmann and H. Rudolph (1975) Photochemical α-cleavage of benzoin derivatives. polar transition states for free-radical formation. J. Am. Chem. Soc. 97, 1519-1525.
44. Turro, N. J. (2000) From boiling stones to smart crystals: supramolecular and magnetic isotope control of radical-radical reactions in Zeolites. Acc. Chem. Res. 33, 637-647.
45. Warrier, M., N. J. Turro and V. Ramamurthy (2000) Heavy cation effect on intersystem crossing between triplet and singlet phenylacyl and benzyl geminate radical pairs within Zeolites. Tetrahedron Lett. 41, 7163-7167.
46. Turro, N. J., I. R. Gould and H. B. Baretz (1993) Absolute rate constants for decarbonylation of phenylacetyl and related radicals. J. Phys. Chem. 97, 531-532.
47. Lunazzi, L., K. U. Ingold and J. C. Scaiano (1983) Absolute rate constants for the decarbonylation of the phenylacetyl radical. J. Phys. Chem. 87, 529.
48. Dasaratha Reddy, G., G. Usha, K. V. Ramanathan and V. Ramamurthy (1987) Modification of photochemical reactivity by cyclodextrin complexation: competitive Norrish Type I and Type II reactions of benzoin alkyl ethers. J. Org. Chem. 52, 5521-5528.
49. Ramamurthy, V., D. R. Corbin and D. F. Eaton (1990) Modification of photochemical reactivity by zeolites. Norrish Type I and Type II reactions of ketones as photochemical probes of the interior of Zeolites. J. Org. Chem. 55, 5269-5278.
50. Cowan, D. O. and R. L. Drisko (1976) Elements of Organic Photochemistry. Plenum Press, New York.
51. Ramamurthy, V. (1986) Organic photochemistry in organized media. Tetrahedron 42, 5753-5839.
52. Nerbonne, J. M. and R. G. Weiss (1979) Liquid crystalline solvents as mechanistic probes. 3. The influence of ordered media on the efficiency of the photodimerization of acenaphthylene. J. Am. Chem. Soc. 101, 402-407.
53. Yoshizawa, M. Y., Y. Takeyama, T. Kusukawa and M. Fujita (2002) Cavity-directed, highly stereoselective [2+2] photodimerization of olefins within self-assembled coordination cages. Angew. Chem. Int. Ed. 41, 1347-1349.
54. Ramamurthy, V., D. R. Corbin, C. V. Kumar and N. J. Turro (1990) Modification of photochemical reactivity by zeolites: cation controlled photodimerisation of acenaphthylene within faujasites. Tetrahedron Lett. 31, 47-50.
55. Livinston, R. and K. S. Wei (1967) Reversible photochemical dimerization of acenaphthylene. I. Reaction in liquid solutions. J. Phys. Chem. 71, 541-547.