Nanochannel array within a multilayered network of a planarized dehydro[24]annulene

Organic Letters

Volumn 12, Issue 10, 2010, Pages 2346-2349

  Suzuki, Mitsuharu ^a   Comito, Angelo ^a   Khan, Saeed I ^a   Rubin, Yves ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77952336137     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1006967     Document Type: Article

References (38)

1. Hisaki, I.; Sonoda, M.; Tobe, Y. Eur. J. Org. Chem. 2006, 83, 3-847
2. Bunz, U. H. F.; Rubin, Y.; Tobe, Y. Chem. Soc. Rev. 1999, 28, 107-119
3. Dosa, P. I.; Erben, C.; Iyer, V. S.; Vollhardt, K. P. C.; Wasser, I. M. J. Am. Chem. Soc. 1999, 121, 10430-10431
4. Boese, R.; Matzger, A. J.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1997, 119, 2052-2053
5. Laskoski, M.; Steffen, W.; Morton, J. G. M.; Smith, M. D.; Bunz, U. H. F. J. Am. Chem. Soc. 2002, 124, 13814-13818
6. Baughman, R. H.; Yee, K. C. J. Polym. Sci., Part A: Polym. Chem. 1974, 12, 2467-2475
7. Day, D.; Lando, J. B. J. Polym. Sci., Part B: Polym. Phys. 1978, 16, 1009-1022
8. Enkelmann, V.; Graf, H. J. Acta Crystallogr., Sect. B: Struct. Sci. 1978, 34, 3715-3719
9. Banerjie, A.; Lando, J. B.; Yee, K. C.; Baughman, R. H. J. Polym. Sci., Part B: Polym. Phys. 1979, 17, 655-662
10. Yee, K. C. J. Polym. Sci., Part A: Polym. Chem. 1979, 17, 3637-3646
11. Zhou, Q.; Carroll, P. J.; Swager, T. M. J. Org. Chem. 1994, 59, 1294-1301
12. Baldwin, K. P.; Matzger, A. J.; Scheiman, D. A.; Tessier, C. A.; Vollhardt, K. P. C.; Youngs, W. J. Synlett 1995, 1215-1218
13. Haley, M. M.; Bell, M. L.; English, J. J.; Johnson, C. A.; Weakley, T. J. R. J. Am. Chem. Soc. 1997, 119, 2956-2957
14. Baughman, R. H.; Biewer, M. C.; Ferraris, J. P.; Lamba, J. S. Synth. Met. 2004, 141, 87-92
15. Bunz, U. H. F.; Enkelman, V. Chem.- Eur. J. 1999, 5, 263-266
16. Lauher, J. W.; Fowler, F. W.; Goroff, N. S. Acc. Chem. Res. 2008, 41, 1215-1229
17. Li, Z.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 2009, 131, 634-643
18. Spitler, E. L.; Johnson, C. A.; Haley, M. M. Chem. Rev. 2006, 106, 5344-5386
19. Curtis, S. M.; Le, N.; Fowler, F. W.; Lauher, J. W. Cryst. Growth Des. 2005, 5, 2313-2321
20. Lee, J. H.; Curtis, M. D.; Kampf, J. W. Macromolecules 2000, 33, 2136-2144
21. Nakanishi, H.; Matsuda, H.; Kato, M.; Theocharis, C. R.; Jones, W. J. Chem. Soc., Perkin Trans. 2 1986, 1965-1967
22. McQuilkin, R. M.; Garratt, P. J.; Sondheimer, F. J. Am. Chem. Soc. 1970, 92, 6682-6683
23. See Supporting Information for additional details.
24. 2 = 0.1134.
25. For the crystal structure of dehydro[18]annulene 2, see Supporting Information.
26. The pucker angle is defined between a set of two mean planes passing through each edge of opposing ≡C-C=C-C≡ units, e.g., C6′-C5′-C5-C6 and C7′-C8′-C8-C7, Figure 2 a.
27. Nishinaga, T.; Kawamura, T.; Komatsu, K. J. Org. Chem. 1997, 62, 5354-5362
28. Tovar, J. D.; Jux, N.; Jarrosson, T.; Khan, S. I.; Rubin, Y. J. Org. Chem. 1997, 62, 3432-3433
29. Kayser, M. M.; Zhu, J.; Hooper, D. L. Can. J. Chem. 1997, 75, 1315-1321
30. Li, Y.; Rubin, Y.; Diederich, F.; Houk, K. N. J. Am. Chem. Soc. 1990, 112, 1618-1623
31. Rubin, Y.; Knobler, C. B.; Diederich, F. J. Am. Chem. Soc. 1990, 112, 1607-1617
32. Soulen, R. T.; Choi, S. K.; Park, J. D. J. Fluorine Chem. 1973, 3, 141-150
33. Matsuura, A.; Komatsu, K. J. Am. Chem. Soc. 2001, 123, 1768-1769
34. Destro, R.; Pilati, T.; Simonetta, M.; Vogel, E. J. Am. Chem. Soc. 1985, 107, 3185-3191
35. Destro, R.; Pilati, T.; Simonetta, M.; Vogel, E. J. Am. Chem. Soc. 1985, 107, 3192-3196
36. Higuchi, H.; Asano, K.; Nakafuku, K.; Takai, Y.; Ojima, J.; Yamamoto, G. J. Chem. Soc., Perkin Trans. 1 1993, 89-99
37. Andres, J. L.; Castano, O.; Morreale, A.; Palmeiro, R.; Gomperts, R. J. Chem. Phys. 1998, 108, 203-207
38. Steiner, T. Angew. Chem., Int. Ed. 2002, 41, 48-76