Self-assembly of aromatic sulfonamide-amide hybridized molecules: Formation of 2D layers and 3D microporous networks in the solid state

Tetrahedron

Volumn 62, Issue 14, 2006, Pages 3446-3454

  Hu, Zhi Qiang ^a   Chen, Chuan Feng ^a  

^a INSTITUTE OF CHEMISTRY   (China)

Author keywords

2D Layer; 3D Microporous network; Hydrogen bond; Self assembly; Sulfonamide; Superhelice

Indexed keywords

AMIDE; AROMATIC COMPOUND; SULFONAMIDE;

ARTICLE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; HYBRIDIZATION; HYDROGEN BOND; PRIORITY JOURNAL; PROTEIN SECONDARY STRUCTURE; SOLID STATE; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 33644910501     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.12.058     Document Type: Article

References (49)

1. J.-M. Lehn Angew. Chem., Int. Ed. Engl. 27 1988 89 112
2. J.-M. Lehn Angew. Chem., Int. Ed. Engl. 29 1990 1304 1319
3. A.G. Orpen, D. Braga, and F. Grepioni Crystal Engineering: from Molecules and Crystals to Materials 1999 Kluwer Academic Boston
4. G.R. Desiraju Crystal Engineering: The Design of Organic Solids 1989 Elsevier Amsterdam
5. Y. Wang, X.J. Wang, Y. Guo, Z.C. Cui, Q. Lin, W.Z. Yu, L.Y. Liu, D.M. Zhang, and B. Yang Langmuir 20 2004 8952 8954
6. F.F. Gao, G.S. Zhu, Y. Chen, and S.L. Qiu J. Phys. Chem. B. 108 2004 3426 3430
7. P. Ganpadhyay, and T.P. Radhakrishnan Angew. Chem., Int. Ed. 40 2001 2451 2455
8. J.C. Macdonald, and G.M. Whitesides Chem. Rev. 94 1994 2383 2420
9. M.J. Krische, and J.-M. Lehn Struct. Bond. 96 2000 3 29
10. G.R. Desiraju Acc. Chem. Res. 35 2002 565 573
11. T. Steiner Angew. Chem., Int. Ed. 41 2002 48 76
12. J.N. Moorthy, R. Natarajan, P. Mal, and P. Venugopalan J. Am. Chem. Soc. 124 2002 6530 6531
13. H. Schlaad, T. Krasia, and M. Antonietti J. Am. Chem. Soc. 126 2004 11307 11310
14. C.E. Marjo, R. Bishop, D.C. Craig, and M.L. Scudder Eur. J. Org. Chem. 2001 863 873
15. M.J. Calhorda Chem. Commun. 2000 801 809
16. A. Corma, F. Rey, J. Rius, M.J. Sabater, and S. Valencla Nature 431 2004 287 290
17. Z.T. Yu, Z.L. Liao, Y.S. Jiang, G.H. Li, G.D. Li, and J.S. Chen Chem. Commun. 2004 1814 1815
18. A.D. Santis, A. Forni, R. Liantonio, P. Metrangolo, T. Pilati, and G. Resnati Chem. Eur. J. 9 2003 3974 3983
19. I. Georgiev, and E. Bosch Cryst. Growth Des. 4 2004 235 239
20. K. Endo, T. Ezuhara, M. Koyanagi, H. Masuda, and Y. Aoyama J. Am. Chem. Soc. 119 1997 499 505
21. M.P. Lightfoot, F.S. Mair, R.G. Pritchard, and J.E. Warren Chem. Commun. 1999 1945 1946
22. G. Blay, I. Fernández, J.R. Pedro, R. Ruiz-García, M.C. Muñoz, J. Cano, and R. Carrasco Eur. J. Org. Chem. 2003 1627 1630
23. M.P. Suh, K.S. Min, J.W. Ko, and H.J. Choi Eur. J. Inorg. Chem. 2003 1373 1379
24. C.B. Aaskeröy, and A.M. Beatty Chem. Commun. 1998 1067 1068
25. Q. Yu, T.E. Baroni, L. Liable-Sands, G.P.A. Yap, A.L. Rheingold, and A.S. Borovik Chem. Commun. 1999 1467 1468
26. G.T.R. Palmore, and M.T. McBride Chem. Commun. 1998 145 146
27. One example on absolute helical arrangement of sulfonamide through CH-π interaction in the crystal, see: I. Azumaya, T. Kato, I. Okamoto, R. Yamasaki, A. Tanatani, K. Yamaguchi, H. Kagechika, and H. Takayanagi Org. Lett. 5 2003 3939 3942
28. B. Gong, C. Zheng, E. Skrzypczak-Jankun, Y. Yan, and J. Zhang J. Am. Chem. Soc. 120 1998 11194 11195
29. B. Gong, C. Zheng, H. Zeng, and J. Zhu J. Am. Chem. Soc. 121 1999 9766 9767
30. B. Gong, C. Zheng, E. Skrzypczak-Jankun, and J. Zhu Org. Lett. 2 2000 3273 3275
31. C. Gennari, M. Gude, D. Potenza, and U. Piarulli Chem. Eur. J. 4 1998 1924 1931
32. J.M. Langenhan, J.D. Fisk, and S.H. Gellman Org. Lett. 3 2001 2559 2562
33. Z.Q. Hu, and C.F. Chen Chem. Commun. 2005 2445 2447
34. B. Kiupel, C. Niederalt, M. Nieger, S. Grimme, and F. Vögtle Angew. Chem., Int. Ed. 37 1998 3031 3034
35. Y. Hamuro, S.J. Geib, and A.D. Hamilton Angew. Chem., Int. Ed. Engl. 33 1994 446 448
36. Y. Hamuro, S.J. Geib, and A.D. Hamilton J. Am. Chem. Soc. 118 1996 7529 7541
37. The majority of achiral organic compounds tend to pack into centrosymmetric crystals. I. Azumaya, D. Uchida, T. Kato, A. Yokoyama, A. Tanatani, H. Takayanagi, and T. Yokozawa Angew. Chem., Int. Ed. 43 2004 1360 1363
38. C. Schmuck Angew. Chem., Int. Ed. 42 2003 2448 2452
39. B. Gong Chem. Eur. J. 7 2001 4336 4342
40. A.E. Rowan, and R.J.M. Nolte Angew. Chem., Int. Ed. 37 1998 63 68
41. H. Mansikkamäki, M. Nissinen, and K. Rissanen Angew. Chem., Int. Ed. 43 2004 1243 1246
42. Z.H. Wang, V. Enkelmann, F. Negri, and K. Müllen Angew. Chem., Int. Ed. 43 2004 1972 1975
43. J.N. Moorthy, R. Natarajan, P. Mal, and P. Venugopalan J. Am. Chem. Soc. 124 2002 6530 6531
44. T. Giorgi, S. Lenga, P. Mariani, M.A. Cremonini, S. Massiero, S. Pieraccini, J.P. Rabe, P. Samorl, G.P. Spada, and G. Gottarelli J. Am. Chem. Soc. 125 2003 14741 14749
45. So far, little is known about the further association of superhelices into highly ordered architectures. (a) R. Custelcean, and M.D. Ward Angew. Chem., Int. Ed. 41 2002 1724 1728
46. Y. Cui, H.L. Ngo, and W. Lin Chem. Commun. 2003 1388 1389
47. Water may come from the moisture during the evaporation of solvent.
48. A similar example about complementary hydrogen bonds between sulfamides and ureas: D.W. Johnson, F. Hof, L.C. Palmer, T. Martin, U. Obst, and J. Rebek Jr. Chem. Commun. 2003 1638 1639
49. C.V. Kumar, K.R. Gopidas, K. Bhattacharyya, P.K. Das, and M.V. Geprge J. Org. Chem. 51 1986 1967 1972