Pyrene photochemistry in solid n-alkane matrices: Comparisons with liquid-phase reactions

Journal of Physical Chemistry A

Volumn 103, Issue 48, 1999, Pages 9794-9804

  Zimerman, Oscar E ^a   Weiss, Richard G ^a  

^a GEORGETOWN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0033518337     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp992339h     Document Type: Article

References (94)

1. Lamotte, M.; Bagno, O.; Lapouyade, R.; Joussot-Dubien, J. C. R. Acad. Sci., Paris, Serie II, 1984, 299, 1321.
2. Lamotte, M.; Joussot-Dubien, J.; Lapouyade, R.; Pereyre, J. In Photophysics and Photochemistry above 6 eV; Lahmani, F., Ed.; Elsevier: Amsterdam, 1985; 577.
3. Lamotte, M.; Pereyre, J.; Joussot-Dubien, J.; Lapouyade, R. J. Photochem. 1987, 38, 177.
4. Lamotte, M.; Pereyre, J.; Lapouyade, R.; Joussot-Dubien, J. J. Photochem. Photobiol. A 1991, 58, 225.
5. Naciri, J.; Weiss; R. G. Macromolecules 1989, 22, 3928.
6. (a) Wunderlich, B. Macromolecular Physics; Academic Press: New York, 1974; Vol. 1.
7. (b) Phillips, P. J. Chem. Rev. 1990, 90, 425 and references therein.
8. (c) Zimerman, O. E.; Cui, C. X.; Wang, X.; Atvarz, T. D. Z.; Weiss, R. G. Polymer 1998, 39, 1177.
9. Small, D. M. The Physical Chemistry of Lipids, Plenum: New York, 1986; p 103.
10. Birks, J. K.; Kazzazz, A. A.; King, T. Proc. R. Soc. (London) 1966, A291, 556.
11. Josephy, E.; Radt, F., Eds. Elsevier's Encyclopedia of Organic Chemistry; Series III, vol. 14; Elsevier: New York, 1940; p 379.
12. Anderson, V. C.; Weiss, R. G. J. Am. Chem. Soc. 1984, 106, 5291.
13. Perrin, D. D.; Argarego, W. L. F. Purification of Laboratory Chemicals, 3rd ed.; Pergamon Press: Exeter, 1988.
14. Rossini, F. D.; Wagman, D. D.; Evans, W. H.; Levine, S.; Jaffe, I. Selected Values of Chemical Thermodynamics Properties. United States Government Printing Office: Washington, D.C., 1952; p 52.
15. Schaerer, A. A.; Busso, C. J.; Smith, A. E.; Skinner, L. B. J. Am. Chem. Soc. 1955, 77, 2017.
16. Sirota, E. B.; Singer, D. M. J. Chem. Phys. 1994, 101, 10873.
17. After filtration, the solid was transferred to a beaker, covered with filter paper, left at room-temperature overnight, and dried under vacuum for several hours.
18. DMS UV Atlas of Organic Compounds; Plenum Press: New York, 1966; Vol. III. p E6/T1.
19. Graselli, J. G.; Ritchey, W. M. Atlas of Spectral Data and Physical Constants for Organic Compounds, 2nd ed.; CRC Press: Cleveland, Ohio, 1975; vol. IV, p 369.
20. Dry ice/ethanol mixture at -72 °C. The transmittance cutoff of the Dewar flask was 310 nm.
21. (a) Eaton, D. F. Pure Appl. Chem. 1990, 62, 1631 and references therein.
22. (b) Knutson, J. R.; Beechem, J. M.; Brand, L. Chem. Phys. Lett. 1983, 102, 501.
23. (c) Beechem, J. M.; Ameloot, M.; Brand, L. Chem. Phys. Lett. 1985, 120, 466.
24. See for instance Part III, Chapter 4 in volumes of the series Photochemistry; Bryce-Smith, D., Ed.; The Chemical Society: London.
25. Lamotte, M. J. Phys. Chem. 1981, 85, 2632.
26. (a) Lamotte, M.; Lapouyade, R.; Pereyre, J.; Joussot-Dubien, J. C. R. Acad. Sci., Paris, Serie C 1980, 211, 290.
27. (b) Rima, J.; Lamotte, M.; Joussot-Dubien, J. Anal. Chem. 1982, 54, 1059.
28. Lamotte, M.; Lapouyade, R.; Pereyre, J.; Joussot-Dubien, J. Chem. Commun. 1980, 725.
29. Sun, Y. P.; Ma, B.; Lawson, G. E.; Bunker, C. E.; Rollins, H. W. Anal. Chim. Acta 1996, 319, 379.
30. (a) Pandey, S.; Acree, W. E., Jr. Anal. Chim. Acta 1997, 343, 155.
31. (b) Sun, Y. P.; Ma, B.; Lawson, G. E.; Bunker, C. E.; Rollins, H. W. Anal. Chim. Acta 1997, 343, 159.
32. Boschi, R.; Schmit, W. Tetrahedron Lett. 1972, 25, 2577.
33. The wave function for the Rydberg electron can be considered independent of the position of individual nuclei. Freund, R. S. In Rydberg States of Atoms and Molecules; Stebbings, R. F., Dunning, F. B., Eds.; Cambridge University Press: Cambridge, 1983; chapter 10.
34. Weiss, R. G.; Ramamurthy, V.; Hammond, G. S. Acc. Chem. Res. 1993, 26, 530.
35. (a) Mitchell, R. H.; Lai, Y. H.; Williams, R. V. J. Org. Chem. 1979, 44, 4733.
36. (b) Lapouyade, R.; Pereyre, J.; Garrigues, P. C. R. Acad. Sci., Paris, Serie II 1986, 10, 903.
37. Electronic densities were obtained from ab initio calculations at the HF/6-31 g* level of theory using the Gaussian 94 program by Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheesman, J. R.; Keith, T.; Peterson, G. A.; Ortiz, J. V.; Foresman, J. B.; Ciolowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andre, J. L.; Reploge, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. from Gaussian, Inc. Pittsburgh, PA, 1995.
38. Joussot-Dubien, J.; Lamotte, M.; Pereyre, J. J. Photochem. 1981, 347.
39. ex > 180 nm) a Vycor filter.
40. (a) Naciri, J. Ph.D. Thesis, Georgetown University, Washington, D.C., 1989.
41. (b) Zimerman, O. E.; Weiss, R. G., unpublished results.
42. Only the rotator phase crystal transition temperature is included. Some n-alkanes have more than one distinct rotator phase.
43. Kitaigorodskii, A. I. Organic Chemical Crystallography; Consultants Bureau: New York, 1961, Chapter 4.
44. Crissman, J. M.; Passaglia, E.; Eby, R. K.; Colson, J. P. J. Appl. Crystallogr. 1970, 3, 174.
45. Small, D. M. The Physical Chemistry of Lipids; Plenum: New York, 1986, p 103.
46. Dorset, D. L.; Strauss, H. L.; Snyder, R. G. J. Phys. Chem. 1991, 95, 938.
47. Boese, R.; Weiss, H.-C.; Bläser, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 988.
48. Kelusky, E. C.; Smith, I. C. P.; Ellinger, C. A.; Cameron, D. G. J. Am. Chem. Soc. 1984, 106, 2267.
49. (a) Doucet, J.; Denicolò, I.; Craievich, A. J. Chem. Phys. 1981, 75, 1523.
50. (b) Denicolo, I.; Doucet, J.; Craievich, A. F. J. Chem. Phys. 1983, 78, 1465.
51. (c) Maroncelli, M.; Strauss, H. L.; Snyder, R. G. J. Chem. Phys. 1985, 82, 2811.
52. (d) Okazaki, M.; Toriyama, K. J. Phys. Chem. 1989, 93, 2883.
53. Gang, H.; Gang, O.; Shao, H. H.; Wu, X. Z.; Patel, J.; Hsu, C. S.; Deutsch, M.; Ocko, B. M.; Sirota, E. B. J. Phys. Chem. B 1998, 102, 2754.
54. Egelstaff, P. A. J. Chem. Phys. 1970, 53, 2590.
55. Sherwood, J. N., Ed. The Plastically Crystalline State: Orientalionally Disordered Crystals; Wiley: New York, 1979; p 29 and refs cited therein.
56. (a) Thulstrup, E. W.; Eggers, J. H. Chem. Phys. Lett. 1968, 1, 690.
57. (b) Thulstrup, E. W.; Michl, J.; Eggers, J. H. J. Phys. Chem. 1970, 74, 3868.
58. (c) Phillips, P. J. Chem. Rev. 1990, 90, 425.
59. (a) Naciri, J.; He, Z.; Costantino, R. M.; Lu, L.; Hammond, G. S.; Weiss, R. G. In Multi-Dimensional NMR, FT-IR/Raman, and Fluorescence Spectroscopy of Polymers; Urban, M. W., Provder, T., Eds.; American Chemical Society: Washington D.C., 1995; Chapter 25.
60. (b) Cui, C.; Naciri, J.; He, Z.; Jenkins, R. M.; Lu, L.; Ramesh, V.; Hammond, G. S.; Weiss, R. G. Quimica Nova 1993, 16, 578.
61. (c) Cui, C.; Weiss, R. G. J. Am. Chem. Soc. 1993, 115, 9820.
62. (d) Talhavini, M.; Atvars, T. D. Z.; Cui, C.; Weiss, R. G. Polymer 1996, 37, 4365.
63. Camerman, A.; Trotter, J. Acta Crystallogr. 1965, 18, 636.
64. (a) Konwerska-Hrabowska, J. Appl. Spectrosc. 1985, 39, 434.
65. (b) Konwerska-Hrabowska, J. Appl. Spectrosc. 1985, 39, 976.
66. Mathisen, H.; Norman, N.; Pederson, B. F. Acta Chem. Scand. 1967, 21, 127.
67. The folded plane is aproximately (001). It is an uneven surface because of the presence of folds, loops, and linking chains. (a) Phillips, P. J. Chem. Rev. 1990, 90, 425.
68. (b) Hoffman, J. D.; Davis, G. T.; Lauritzen, J. I. In Treatise on Solid State Chemistry; Hannay, N. B., Ed.; Plenum Press: New York, 1976; Vol. 3.
69. (a) Dorset, D. L. Acta Chim. Hungaria 1993, 130, 389.
70. (b) Clavell-Grunbaum; D.; Strauss, H. L.; Snyder, R. G. J. Phys. Chem. B 1997, 101, 335.
71. Kimura, M.; Nukada, K.; Satake, K.; Morosawa, S.; Tampagake, K. J. Chem. Soc., Perkin Trans. 1 1984, 1431.
72. McGrath, K. J. Ph.D. Thesis, Georgetown University, Washington, D.C., 1994.
73. Birks, J. B. Photophysics of Aromatic Molecules; Wiley: London, 1970; chapter 4.
74. (a) Birks, J. B. Photophysics of Aromatic Molecules; Wiley: London, 1970; p 301.
75. (b) Barltrop, J. A.; Coyle, J. D. Principles of Photochemistry; Wiley: Bristol, 1975; p 105.
76. Yin, G. Z.; Nicol, M. F. J. Phys. Chem. 1985, 89, 1171.
77. (a) Bauer, R. K.; Borenstein, R.; de Mayo, P.; Okada, K.; Rafalska, M.; Ware, W. R.; Wu, K. C. J. Am. Chem. Soc. 1982, 104, 4635.
78. (b) Bauer, R. K.; de Mayo, P.; Okada, K.; Ware, W. R.; Wu, K. C. J. Phys. Chem. 1983, 87, 460.
79. Bauer, R. K.; de Mayo, P.; Ware, W. R.; Wu, K. C. J. Phys. Chem. 1982, 86, 3781.
80. 59a-c (a) McDonald, R. J.; Selinger, B. K. Aust. J. Chem. 1971, 24, 249.
81. (b) Ferguson, J. J. Chem. Phys. 1965, 43, 306.
82. (c) Mataga, N.; Torihashi, Y.; Ota, Y. Chem. Phys. Lett. 1967, 1, 385.
83. (a) Reynders, P.; Kühnle, W.; Zachariasse, K. A. J. Am. Chem. Soc. 1990, 112, 3929.
84. (b) Reynders, P.; Kühnle, W.; Zachariasse, K. A. J. Phys. Chem. 1990, 94, 4073.
85. Avis, P.; Porter, G. J. Chem Soc. 1973, 34, 1057.
86. See for instance: Kasha, M.; Rawls, H. R.; El-Bayoumi, M. Pure Appl. Chem. 1965, 11, 371.
87. Yau, W. W.; Kirkland, J. J.; Ely, D. D. Modern Size-Exclusion Liquid Chromatography; Wiley: New York, 1979.
88. Jenkins, R. M.; Weiss, R. G. Langmuir 1990, 6, 1408.
89. (a) Toriyama, K.; Nunome, K.; Iwasaki, M. J. Phys. Chem. 1986, 90, 6836.
90. (b) Toriyama, K.; Iwasaki, M.; Nunome, K.; Matsuura, K. Radiat. Phys. Chem. 1990, 37, 15.
91. See for instance: (a) Weiss, R. G.; Treanor, R. L.; Nunez, A. Pure Appl. Chem. 1988, 60, 999.
92. (b) Nunez, A.; Hammond, G. S.; Weiss, R. G. J. Am. Chem. Soc. 1992, 114, 10258.
93. Lansac, Y.; Glaser, M. A.; Clark, N. A.; Lavrentovich, O. D. Nature 1999, 398, 54.
94. Evans, D. F. J. Chem. Soc. 1957, 1351.