Laser photolysis of liquid hexafluorobenzene: graphitic and fluorine-containing carbon formation at ambient temperature

Abstract

ArF laser photolysis of liquid hexafluorobenzene affords a number of aromatic fluorocarbons, graphitic carbon and a fluorine containing polymeric C/F material. The preponderance of decafluorobiphenyl among the perfluoroaromatic products reveals the importance of the pentafluorophenyl radical combinations in the initial stages of photolysis. The C/F material is judged to arise from polymerization of fluoroalkyne transients. The graphite formation represents a unique mode of photolytic liquid-phase graphitization of perfluoroaromatic compounds.

References

1. D. Bryce-Smith and A. Gilbert, Tetrahedron, 1976, 32, 1309.
2. A. Gilbert, in CRC Handbook of Organic Photochemistry and Photobiology, ed. W. M. Horspool and P.-S. Song, CRC Press, Boca Raton, FL, 1995, ch. 18.
3. M. C. Sauer, A. D. Trifunac, D. B. McDonald and R. Cooper, J. Phys. Chem., 1984, 88, 4096.
4. A. Liu, M. C. Sauer and A. D. Trifunac, J. Phys. Chem., 1994, 98, 9546.
5. R. Srinivasan and A. P. Ghosh, Chem. Phys. Lett., 1988, 143, 546.
6. Y. Tsuboi, K. Hatanaka, H. Fukumura and H. Masuhara, J. Phys. Chem., 1994, 98, 11 237.
7. J. Singh, M. Vellaikal and J. Narayan, J. Appl. Phys., 1993, 73, 4351.
8. J. Pola, M. Urbanová, Z. Bastl, Z. Plzák, J. Šubrt, V. Vorlíček, I. Gregora, C. Crowley and R. Taylor, Carbon, 1997, 35, 605.
9. S. E. Stein, Carbon, 1981, 19, 421.
10. I. C. Lewis, Carbon, 1982, 20, 519.
11. P. L. Walker, Carbon, 1990, 28, 261.
12. Z. Plzák, M. Polanská and M. Suchánek, J. Chromatogr. A, 1995, 699, 241.
13. J. R. Majer, Adv. Fluorine Chem., 1961, 2, 55.
14. W. J. Feast and W. E. Preston, Tetrahedron, 1972, 28, 2805.
15. C.-M. Hu, F. Long and Z.-Q. Xu, J. Fluorine Chem., 1990, 48, 29.
16. J. L. Cotter, J. Chem. Soc., 1965, 1520.
17. A. E. Hughes and B. A. Sexton, J. Electron Spectrosc. Relat. Phenom., 1988, 46, 31.
18. D. A. Shirley, Phys. Rev. B, 1972, 5, 4709.
19. J. H. Scofield, J. Electron Spectrosc. Relat. Phenom., 1976, 8, 129.
20. G. Camaggi, F. Gozzo and G. J. Cevidalli, Chem. Commun., 1966, 313.
21. I. Haller, J. Am. Chem. Soc., 1966, 88, 2070.
22. R. L. Whetten, K.-J. Fu, R. S. Tapper and E. R. Grant, J. Phys. Chem., 1983, 87, 1484.
23. E. N. Okafo and E. Whittle, Int. J. Chem. Kinet., 1978, 10, 591.
24. R. Gilbert and A. Theoret, J. Phys. Chem., 1976, 80, 1017.
25. M. J. Kroch, S. J. W. Price and W. F. Yared, Can. J. Chem., 1974, 52, 2673.
26. S. J. W. Price and H. Sapiano, Can. J. Chem., 1974, 52, 4109.
27. M. T. Duignan, E. Grunwald and S. Speiser, J. Phys. Chem., 1983, 87, 4387 and references therein.
28. H. Bürger and S. Sommer, J. Chem. Soc., Chem. Commun., 1991, 456.
29. K. Sugawara, A. Watanabe, Y. Koga, H. Takeo, K. Fukuda, J. Hiraishi and C. Matsumura, J. Phys. Chem., 1989, 93, 3647.
30. A. Watanabe, Y. Koga, K. Sugawara, H. Takeo, K. Fukuda and C. Matsumura, Spectrochim. Acta, Part A, 1990, 46, 463.
31. NIST X-ray Photoelectron Spectroscopy Database, US Dept. of Commerce, Gaithsburg, 1989.
32. D. Briggs and M. P. Seah, Practical Surface Analysis, Vol. 1, Auger and Photoelectron Spectroscopy, Wiley, Chichester, 1994, p. 622.
33. J. F. Moulder, W. F. Stickle, P. E. Sobol and K. D. Bomben, Handbook of X-ray Photoelectron Spectroscopy, ed. J. Chastain, Perkin Elmer Co., Physical Electronics Div., Eden Praire, MN, 1992, p. 234.
34. A. A. Galuska, H. H. Madenand and R. E. Allred, Appl. Surf. Sci., 1988, 32, 253.
35. J. M. Lascovich, R. Giorgi and S. Scaglione, Appl. Surf. Sci., 1991, 47, 17.
36. M. A. Tamor and W. C. Vassell, J. Appl. Phys., 1994, 76, 3823.
37. J. Wagner and P. Lautenschlager, J. Appl. Phys., 1986, 59, 2044.
38. R. d'Agostino, R. Lamendola, P. Favia and A. Giquel, J. Vac. Sci. Technol. A, 1994, 12, 308.