Hydrogen bonding and cooperativity effects on the assembly of alkyl- and perfluoroalkyl-sulfonyl naphthols: F···F non-bonded interactions†

Abstract

Important differences in the crystal packing of 6-perfluorohexylsulfonyl-2-naphthol (1F) including π–π stacking aromatic interactions and F···F non-bonded contacts, in contrast to its nonfluorinated analog (1), appear to translate into differences between their photophysical properties both in the solid state and in solution.

References

1. Y. Wei, W. Wang, J. M. Yeh, B. Wang, D. C. Yang and J. K. Murray, Adv. Mater., 1994, 6, 372.
2. J. M. Harvard, M. Yoshida, D. Pasini, N. Vladimirov, J. M. J. Frechet, D. R. Medeiros, K. Patterson, S. Yamada, C. G. Willson and J. D. Byers, J. Polym. Sci., Part A: Polym. Chem., 1999, 37, 1225; H. S. Yu, T. Yamashita and K. Horie, Macromolecules, 1996, 29, 1144; K. H. Chae, I. J. Park and M. H. Choi, Bull. Korean Chem. Soc., 1993, 14, 614.
3. S. G. Moon, K. Naitoh and T. Yamaoka, Chem. Mater., 1993, 5, 1315.
4. S. T. Kim, J. B. Kim, C. M. Chung and K. D. Ahn, J. Appl. Polym. Sci., 1997, 66, 2507; J. P. Chen, J. P. Gao and Z. Y. Wang, J. Polym. Sci., Part A: Polym. Chem., 1997, 35, 9; H. K. Kim and C. K. Ober, Polym. Bull., 1992, 28, 33.
5. For a recent review see: M. Shirai and M. Tsunooka, Bull. Chem. Soc. Jpn., 1998, 71, 2483 and references cited therein.
6. L. G. Arnaut and S. J. Formosinho, J. Photochem. Photobiol. A: Chem., 1993, 75, 1; L. G. Arnaut and S. J. Formosinho, J. Photochem. Photobiol. A: Chem., 1993, 75, 21.
7. K. M. Solntsev, D. Huppert, L. M. Tolbert and N. Agmon, J. Am. Chem. Soc., 1998, 120, 7981; E. Pines, D. Pines, T. Barak, B.-Z. Magnes, L. M. Tolbert and J. E. Haubrich, Ber. Bunsenges. Phys. Chem., 1998, 102, 511; D. Huppert, L. M. Tolbert and S. Linares-Samaniego, J. Phys. Chem., 1997, 101, 4602; I. Carmeli, D. Huppert, L. M. Tolbert and J. E. Huppert, Chem. Phys. Lett., 1996, 260, 109.
8. K. Hansch, A. Leo and R. W. Taft, Chem. Rev., 1991, 91, 165.
9. N. V. Kondratenko, V. I. Popov, A. A. Kolomeitsev, E. P. Saenko, V. V. Prezhdo, A. E. Lutskii and L. M. Yagupol'skii, Zh. Org. Khim., 1980, 16, 1049.
10. D. H. McDaniel and H. C. Brown, J. Org. Chem., 1958, 23, 420.
11. P. Karrer and P. Leiser, Helv. Chim. Acta, 1944, 27, 678.
12. S. Fujita, Synthesis, 1981, 423.
13. G. Biswas and D. Mal, J. Chem. Res. (S), 1988, 308.
14. V. N. Boiko and G. M. Shchupak, J. Fluorine Chem., 1994, 69, 207.
15. S. Oae and H. Togo, Bull. Chem. Soc. Jpn., 1983, 56, 3802.
16. J. Kowalik, C. Clower and L. M. Tolbert, to be published.
17. K. Shirai, M. Matsuoka and K. Fukunishi, Dyes Pigm., 1999, 42, 95.
18. C.-H. Tung and H.-F. Ji, J. Phys. Chem., 1995, 99, 8311; C.-H. Tung and H.-F. Ji, J. Chem. Soc., Faraday Trans., 1995, 91, 2761.
19. M. C. Calama, R. Hulst, R. Fokkens, N. M. M. Nibbering, P. Timmerman and D. N. Reinhoudt, Chem. Commun., 1998, 1021; K. A. Jolliffe, M. C. Calama, R. Fokkens, N. M. M. Nibbering, P. Timmerman and D. N. Reinhoudt, Angew. Chem., Int. Ed., 1998, 37, 1247; C. J. Kepert, D. Hesek, P. D. Beer and M. J. Rosseinsky, Angew. Chem., Int. Ed., 1998, 37, 3158; M. Mascal, J. Hansen, P. S. Fallon, A. J. Blake, B. R. Heywood, M. H. Moore and J. P. Turkenburg, Eur. Chem. J., 1999, 5, 381.
20. A. Gavezzotti and G. Filippini, Chem. Commun., 1998, 287; A. Gavezzotti, Eur. Chem. J., 1999, 5, 567.
21. W. C. Hamilton and J. A. Ibers, Hydrogen Bonding in Solids, W. A. Benjamin, New York, Amsterdam, 1968, p. 16.
22. A. Bondi, J. Phys. Chem., 1964, 68, 441.
23. N. Hayashi, T. Mori and K. Matsumoto, Chem. Commun., 1998, 1905.
24. G. Pimentel and R. Spratley, Chemical Bonding Clarified Through Quantum Mechanics, Holden-Day, San Francisco, California, 1969, p. 256.
25. H. Langhals, T. Potrawa, H. Nöth and G. Linti, Angew. Chem., Int. Ed. Engl., 1989, 28, 478.