"Latent" trialkylphosphine and trialkylphosphine oxide organogelators activated by broønsted and lewis acids

Langmuir

Volumn 19, Issue 4, 2003, Pages 1036-1046

  Wang, Caihua ^a   Robertson, Allen ^b   Weiss, Richard G ^a  

^a GEORGETOWN UNIVERSITY   (United States)

^b Cytec Canada Inc   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL ACTIVATION; DISSOCIATION; GELATION; HEATING; MATHEMATICAL MODELS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC COMPOUNDS; SALTS; SOLS; THERMAL EFFECTS; X RAY POWDER DIFFRACTION;

BRONSTED ACIDS; LEWIS ACIDS; LOW MOLECULAR MASS ORGANOGELATORS; TRIALKYLPHOSPHINE; TRIALKYLPHOSPHINE OXIDE;

GELS;

EID: 0037452741     PISSN: 07437463     EISSN: None     Source Type: Journal    
DOI: 10.1021/la026631j     Document Type: Article

References (65)

1. (a) Terech, P.; Weiss, R. G. Chem. Rev. 1997, 97, 3133.
2. (b) Abdallah, D. J.; Weiss, R. G. Adv. Mater. 2000, 12, 1237.
3. (a) Abdallah, D. J.; Weiss, R. G. Langmuir 2000, 16, 352.
4. (b) Abdallah, D. J.; Sirchio, S. A.; Weiss, R. G. Langmuir 2000, 16, 7558.
5. (c) Willemen, H. M.; Vermonden, T.; Marcelis, A. T. M.; Sudhölter, J. R. Langmuir 2002, 18, 7102.
6. Van Esch, J. H.; Feringa, B. L. Angew. Chem., Int. Ed. 2000, 39, 2263.
7. Lin, Y. C.; Kachar, B.; Weiss, R. G. J. Am. Chem. Soc. 1989, 111, 5542.
8. (a) Tata, M.; John, V. T.; Waguespack, Y. Y.; McPherson, G. L. J. Am. Chem. Soc. 1994, 116, 9464.
9. (b) Wang, R.; Geiger, C.; Chen, L.; Swanson, B.; Whitten, D. G. J. Am. Chem. Soc. 2000, 122, 2399.
10. (a) Murata, K.; Aoki, M.; Nishi, T.; Ikeda, A.; Shinkai, S. J. Chem. Soc., Chem. Commun. 1991, 1715.
11. (b) Murata, K.; Aoki, M.; Suzuki, T.; Harada, T.; Kawabata, H.; Komori, T.; Ohseto, F.; Ueda, K.; Shinkai, S. J. Am. Chem. Soc. 1994, 116, 6664.
12. (c) Ahmed, S. A.; Sallenave, X.; Fages, F.; Mieden-Gundert, G.; Müller, U.; Vögtle, F.; Pozzo, J.-L. Langmuir 2002, 18, 7096.
13. Aggeli, A.; Bell, M.; Boden, N.; Keen, J. N.; Knowles, P. F.; McLeish, T. C. B.; Pitkeathly, M.; Radford, S. E. Nature 1997, 386, 259.
14. (a) Jung, J. H.; Ono, Y.; Sgubjau, S. Tetrahedron Lett. 1999, 40, 8395.
15. (b) Engelkamp, H.; Middelbeek, S.; Nolte, R. J. M. Science 1999, 284, 785.
16. (c) Ihara, H.; Sakurai, T.; Yamada, T.; Hashimoto, T.; Takafuji, M.; Sagawa, T.; Hachisako, H. Langmuir 2002, 18, 7120.
17. Frkanec, L.; Jokić, M.; Makarević, J.; Wolsperger, K.; Žinić, M. J. Am. Chem. Soc. 2002, 124, 9716.
18. Pozzo, J.-L.; Claviewm, G. M.; Desvergne, J.-P. J. Mater. Chem. 1998, 8, 2575.
19. George, M.; Weiss, R. G. J. Am. Chem. Soc. 2001, 123, 10393.
20. (a) Lu, L.; Weiss, R. G. Chem. Commun. 1996, 2029.
21. (b) Abdallah, D. J.; Lu, L.; Weiss, R. G. Chem. Mater. 1999, 11, 2907.
22. (c) Abdallah, D. J.; Weiss, R. G. Chem. Mater. 2000, 12, 406.
23. Abdallah, D. J. Ph.D. Thesis, Georgetown University, Washington, DC, 2000.
24. (a) Terech, P.; Allegraud, J. J.; Garner, C. M. Langmuir 1998, 14, 3991.
25. (b) Hafkamp, R. J. H.; Feiters, M. C.; Nolte, R. J. M. J. Org. Chem. 1999, 64, 412.
26. (c) Ajayaghosh, A.; George, S. J. J. Am. Chem. Soc. 2001, 123, 5148.
27. BH+.
28. Kosolapoff, G. M.; Maier, L. Organic Phosphorus Compounds; Wiley-Interscience: New York, 1972; Vol. 3, p 389.
29. (a) Goehring, M. B.; Thielemann, H. Z. Anorg. Allg. Chem. 1961, 308, 33.
30. (b) Maciel, G. E.; James, R. V. Inorg. Chem. 1964, 3, 1560.
31. (c) Albright, T. A.; Freeman, W. J.; Schweizer, E. E. J. Org. Chem. 1975, 40, 3437.
32. Burg, A. B.; Mckee, W. E. J. Am. Chem. Soc. 1951, 73, 4590.
33. Franks S.; Hartley, F. R.; McCaffrey, D. J. A. J. Chem. Soc., Perkin Trans. 1 1979, 3029.
34. Vogel, A. I. Vogel's Textbook of Practical Organic Chemistry, 5th ed.; Longman: Essex, U.K., 1989; p 438.
35. Takahashi, A.; Sakai, M.; Kato, T. Polym. J. 1980, 12, 335.
36. Amman, C.; Meier, P.; Merbach, A. E. J. Magn. Reson. 1982, 46, 319.
37. JADE, release 5.0.35 (SPS); Materials Data Inc.: Livermore, CA.
38. Quin, L. D. A Guide to Organophosphorus Chemistry; Wiley-Interscience: New York, 2000; p 13.
39. Gilheany, D. G. In The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; Wiley: Chichester, U.K., 1992; Vol. 2, Chapter 1.
40. Haake, P.; Cook, R. D.; Hurst, G. H. J. Am. Chem. Soc. 1967, 89, 2650.
41. Yakshin, V. V.; Meshcheryakov, N. M.; Ignatov, M. E.; Laskorin, B. I.; Yagodin, V. G.; Ilin, E. G. J. Gen. Chem. USSR 1985, 55, 1266.
42. CRC Handbook of Chemistry and Physics, 82nd ed.; Lide, D. R., Ed.; CRC Press: Boca Raton, FL, 2001-2002.
43. Halmann, M.; Pinchas, S. J. Chem. Soc. 1958, 3264.
44. (a) Copley, D. B.; Fairbrother, F.; Miller, J. R.; Thompson, A. Proc. Chem. Soc. 1964, 300.
45. (b) Temple, R. D.; Tsuno, Y.; Lefflerm, H. E. J. Org. Chem. 1963, 28, 2495.
46. March, J. Advanced Organic Chemistry: reactions, mechanisms, and structure, 3rd ed.; Wiley: New York, 1985; p 220.
47. Ramirez, F.; Dershowitz, S. J. Org. Chem. 1959, 24, 704.
48. Hadzi, D. J. Chem. Soc. 1962, 5128.
49. Chawla, B.; Mehta, S. K. J. Phys. Chem. 1984, 88, 2650.
50. (a) Denney, B. D.; Denny, D. Z.; Wilson, L. A. Tetrahedron Lett. 1968, 85.
51. (b) Burford, N.; Royan, B. W.; Spence, R. J. Chem. Soc., Dalton Trans. 1990, 2111.
52. Hadzi, D.; Kobilarov, N. J. Chem. Soc. A 1966, 439.
53. Hadzi, D.; Klofutar, C.; Oblak, S. J. Chem. Soc. A 1968, 905.
54. Although the exact physical properties of salts produced in another laboratory are expected to differ slightly from those reported here, the variations should be small and the overall results should be the same. In support of that hypothesis, gelation experiments with different batches of hydroxytrioctadecylphosphonium chloride gave indistinguishable results. LMOG purity is not a critical issue here.
55. 31P resonances of the salt (77 ppm) and the phosphine oxide (49 ppm) were a easily distinguished.
56. Additional small peaks from protons attached to unsaturated carbons (Figure 7S in the Supporting Information) from other unidetified materials could not be removed by several attempted purification procedures. The overall intensity of the impurity, based on the integrated proton peak intensities, is less than 1%.
57. Abdallah, D. J.; Bachman, R. E.; Perlstein, J.; Weiss, R. G. J. Phys. Chem. B 1999, 103, 9269.
58. Estimated from data in Landolt-Börnstein Numerical Data and Functional Relationships in Science and Technology. New Series, Group IV; Madelung, O., Eds.; Spring-Verlag: Berlin, 1991; Vol. 6.
59. (a) Furman, I.; Weiss, R. G. Langmuir 1993, 9, 2084.
60. (b) Mukkamala, R.; Weiss, R. G. Langmuir 1996, 12, 1474.
61. Ostuni, E.; Kamaras, P.; Weiss, R. G. Angew. Chem., Int. Ed. Engl. 1996, 35, 1324.
62. Bordwell, F. G.; Liu, W.-Z. J. Am. Chem. Soc. 1996, 118, 8777.
63. Lescanne, M.; Colin, A.; Mondain-Monval, O.; Heuze, K.; Fages, F.; Pozzo, J.-L. Langmuir 2002, 18, 7151.
64. Abdallah, D. J.; Robertson, A.; Hsu, H.-F.; Weiss, R. G. J. Am. Chem. Soc. 2000, 122, 3053.
65. Cole, A. C.; Jensen, J. L.; Ntai, I.; Tran, K. L. T.; Weaver, K. J.; Forbes, D. C.; Davis, J. H., Jr. J. Am. Chem. Soc. 2002, 124, 5962.