Formation of gold-like metal-lustrous inclusion crystals from 1-phenyl-2,5-bis[5-(tricyanoethenyl)-2-thienyl]pyrrole host and and electron-donating aromatic guest

Organic and Biomolecular Chemistry

Volumn 1, Issue 21, 2003, Pages 3845-3850

  Ogura, Katsuyuki ^a   Zhao, Rui ^a   Mizuoka, Takashi ^a   Akazome, Motohiro ^a   Matsumoto, Shoji ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CRYSTAL STRUCTURE; CRYSTALLIZATION; DIFFERENTIAL SCANNING CALORIMETRY; MOLECULES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STOICHIOMETRY; SYNTHESIS (CHEMICAL); TEMPERATURE; X RAY POWDER DIFFRACTION;

ANISOLE; DIMETHOXYBENZENES; INDENE; TRICYANOETHENYL GROUP; X-RAY STRUCTURAL ANALYSES;

AROMATIC COMPOUNDS;

EID: 0344981489     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b302689b     Document Type: Article

References (49)

1. K. Ogura, R. Zhao, H. Yanai, K. Maeda, R. Tozawa, S. Matsumoto and M. Akazome, Bull. Chem. Soc. Jpn., 2002, 75, 2359.
2. R. Zhao, M. Akazome, S. Matsuomoto and K. Ogura, Tetrahedron, 2002, 58, 10225.
3. R. Zhao, S. Matsumoto, M. Akazome and K. Ogura, Tetrahedron, 2002, 58, 10233.
4. K. Ogura, H. Yanai, M. Miokawa and M. Akazome, Tetrahedron Lett., 1999, 40, 8887.
5. For the newest information, trends and prospects in self-assemble, see: (a) J.-M. Lehn, Science, 2002, 295, 2400
6. (b) O. Ikkata and G. ten Brinke, Science, 2002, 295, 2407
7. (c) T. Kato, Science, 2002, 295, 2414
8. (d) G. M. Whitesides and B. Brzybowski, Science, 2002, 295, 2418.
9. (e) D. Philp and J. F. Stoddart, Angew. Chem., Int. Ed. Engl., 1996, 35, 1154
10. (f) C. A. Hunter, Angew. Chem., Int. Ed. Engl., 1995, 34, 1079
11. (g) D. S. Lawrence, T. Jiang and M. Levett, Chem. Rev., 1995, 95, 2229
12. (h) F. M. Menger, S. S. Lee and X. Tao, Adv. Mater., 1995, 7, 669
13. (i) M. R. Ghadiri, Adv. Mater., 1995, 7, 675.
14. (a) M. J. Horner, K. T. Holman and M. D. Ward, Angew. Chem., Int. Ed., 2001, 40, 4045
15. (b) M. Akazome, Y. Ueno, H. Ooiso and K. Ogura, J. Org. Chem., 2000, 65, 68
16. (e) M. Akazome, M. Noguchi, O. Tanaka, A. Sumikawa, T. Uchida and K. Ogura, Tetrahedron, 1997, 53, 8315
17. (d) K. Ogura, T. Uchida, M. Noguchi, M. Minoguchi, A. Murata, M. Fujita and K. Ogata, Tetrahedron lett., 1990, 31, 3331
18. (e) M. Akazome, Y. Yanagita, R. Sonobe and K. Ogura, Bull. Chem. Soc. Jpn., 1997, 70, 2823.
19. In crystals 3 and 5, disordered guests with two crystallographically equivalent alternative conformations were observed because of the asymmetry of the substituent on their central N-phenyl ring.
20. Some information and examples on CH/N type hydrogen-bonding interactions, see: (a) M. Hartmann, D. S. Wetmore and L. Radom, J. Phys. Chem. A, 2001, 105, 4470
21. (b) R. Taylor and O. Kennard, J. Am. Chem. Soc., 1982, 104, 5063
22. (c) P. Seiler and J. D. Dunitz, Helv. Chim. Acta, 1989, 72, 1125
23. (d) K. N. Houk, S. Menzer, S. P. Newton, F. M. Raymo, J. F. Stoddart and D. J. Williams, J. Am. Chem. Soc., 1999, 121, 1479
24. (e) Y. E. Ovchinnikov, O. V. Shishkin, Y. T. Struchkov and G. R. Desiraju, J. Am. Chem. Soc., 1996, 118, 4085
25. K. Sato, S. Arai and T. Yamagishi, Tetrahedron Lett., and the references therein.
26. For examples on [C-H ··· N] hydrogen-bonding interactions, see: (a) T. Fukushima, N. Okazeri, T. Miyashi, K. Suzuki, Y. Yamashita and T. Suzuki, Tetrahedron Lett., 1999, 40, 1175
27. (b) D. S. Reddy, B. S. Goud, K. Paneerselvam and G. R. Desiraju, J. Chem. Soc., Chem. Commun., 1993, 663
28. (c) M. Mazik, D. Bläser and R. Boese, Tetrahedron Lett., 2000, 41, 5827
29. (d) G. R. Desiraju, Angew. Chem., Int. Ed. Engl., 1995, 34, 2311
30. (e) P. N. Jagg, P. F. Kelly, H. S. Rzepa, D. J. Williams, J. D. Woollins and W. Wylie, J. Chem. Soc., Chem. Commun., 1991, 942
31. (f) F. A. Cotton, L. M. Daniels, G. T. Jordan and C. A. Murillo, Chem. Commun., 1997, 1673
32. J. Ashmore, R. Bishop, D. C. Craig and M. L. Scudder, Cryst. Eng. Comm., 2002, 4, 194.
33. For examples on [C-H ··· O] hydrogen-bonding interactions, see: (a) D. J. Sutor, Nature, 1962, 195, 68
34. (b) M. Sandaralingam, Nature, 1966, 217, 35
35. (c) J. A. R. P. Sarma and G. R. Desiraju, J. Chem. Soc., Perkin Trans. 2, 1987, 1195
36. (d) G. R. Desiraju, J. Chem. Soc., Chem. Commun., 1989, 179
37. (e) T. Steiner and G. R. Desiraju, Chem. Commun., 1998, 891
38. (f) G. R. Desiraju, Acc. Chem. Res., 1991, 24, 290
39. (g) G. R. Desiraju, Acc. Chem. Res., 1996, 29, 441
40. (h) C. V. K. Sharma and M. J. Zaworotko, Chem. Commun., 1996, 2655
41. (i) T. Steiner, Chem. Commun., 1997, 727
42. (j) S. G. Bodige, R. D. Rogers and S. C. Blackstock, Chem. Commun., 1997, 1669
43. (k) I. Berger and M. Egli, Chem. Eur. J., 1997, 3, 1400
44. Y.-L. Gu, T. Kar and S. Scheiner, J. Am. Chem. Soc., 1999, 121, 9411.
45. S. Apel, S. Nitsche, K. Beketov, W. Seichter, J. Seidel and E. Weber, J. Chem. Soc., Perkin Trans. 2, 2001, 1212.
46. (a) M. Asakawa, C. L. Brown, S. Menzer, F. M. Raymo, J. F. Stoddart and D. J. Williams, J. Am. Chem. Soc., 1997, 119, 2614
47. (b) P. L. Anelli, P. R. Ashton, R. Ballardini, V. Balzani, M. Delgado, M. T. Gandolfi, T. T. Goodnow, A. E. Kaifer, D. Philp, M. Pietraszkiewicz, L. Prodi, M. V. Reddington, A. M. Z. Slawin, N. Spender, J. F. Stoddart, C. Vicent and D. J. Williams, J. Am. Chem. Soc., 1992, 114, 193
48. S. Tsuzuki, H. Houjou, Y. Nagawa and K. Hiratani, J. Chem. Soc., Perkin Trans. 2, 2002, 1271.
49. A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori and M. Camalli, J. Appl. Cryst., 1994, 27, 435.