Functional self-assembly of hydrogen-bonded networks. Construction of aromatic stacks and columns and cavity-size control via flexible intercalation of 1D chains having orthogonal aromatic substituents

Journal of the American Chemical Society

Volumn 119, Issue 3, 1997, Pages 499-505

  Endo, Ken ^a   Ezuhara, Takayoshi ^a   Koyanagi, Masayuki ^a   Masuda, Hideki ^b   Aoyama, Yasuhiro ^a  

^a KYUSHU UNIVERSITY   (Japan)

^b NAGOYA INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; CRYSTALLOGRAPHY; DRUG DESIGN; DRUG STRUCTURE; POLYMERIZATION;

EID: 0031036251     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja960292x     Document Type: Article

References (20)

1. Desiraju, G. R. Crystal Engineering: The Design of Organic Solids; Elsevier: New York, 1989.
2. For an excellent recent review, see: MacDonald, J. C.; Whitesides, G. M. Chem. Rev. 1994, 94, 2383-2420.
3. (a) See, for example: (a) Ermer, O. J. Am. Chem. Soc. 1988, 110, 3747-3754. (b) Simard, M.; Su, D.; Wuest, J. D. Ibid. 1991, 113, 4696-4698. (c) Copp, S. B.; Subramanian, S.; Zaworotko, M. J. Ibid. 1992, 114, 8719-8720. (d) Reddy, D. S.; Craig, D. C.; Rae, A. D.; Desiraju, G. R. J. Chem. Soc., Chem. Commun. 1993, 1737-1739. (e) Zaworotko, M. J. Chem. Soc. Rev. 1994, 23, 283-288. (f) Batten, S. R.; Hoskins, B. F.; Robson, R. J. Am. Chem. Soc. 1995, 117, 5385-5386. (g) Fujita, M.; Kwon, Y. J.; Sasaki, O.; Yamaguchi, K.; Ogura, K. Ibid. 1995, 117, 7287-7288.
4. (a) See, for example: (a) Ermer, O. J. Am. Chem. Soc. 1988, 110, 3747-3754. (b) Simard, M.; Su, D.; Wuest, J. D. Ibid. 1991, 113, 4696-4698. (c) Copp, S. B.; Subramanian, S.; Zaworotko, M. J. Ibid. 1992, 114, 8719-8720. (d) Reddy, D. S.; Craig, D. C.; Rae, A. D.; Desiraju, G. R. J. Chem. Soc., Chem. Commun. 1993, 1737-1739. (e) Zaworotko, M. J. Chem. Soc. Rev. 1994, 23, 283-288. (f) Batten, S. R.; Hoskins, B. F.; Robson, R. J. Am. Chem. Soc. 1995, 117, 5385-5386. (g) Fujita, M.; Kwon, Y. J.; Sasaki, O.; Yamaguchi, K.; Ogura, K. Ibid. 1995, 117, 7287-7288.
5. (a) See, for example: (a) Ermer, O. J. Am. Chem. Soc. 1988, 110, 3747-3754. (b) Simard, M.; Su, D.; Wuest, J. D. Ibid. 1991, 113, 4696-4698. (c) Copp, S. B.; Subramanian, S.; Zaworotko, M. J. Ibid. 1992, 114, 8719-8720. (d) Reddy, D. S.; Craig, D. C.; Rae, A. D.; Desiraju, G. R. J. Chem. Soc., Chem. Commun. 1993, 1737-1739. (e) Zaworotko, M. J. Chem. Soc. Rev. 1994, 23, 283-288. (f) Batten, S. R.; Hoskins, B. F.; Robson, R. J. Am. Chem. Soc. 1995, 117, 5385-5386. (g) Fujita, M.; Kwon, Y. J.; Sasaki, O.; Yamaguchi, K.; Ogura, K. Ibid. 1995, 117, 7287-7288.
6. (a) See, for example: (a) Ermer, O. J. Am. Chem. Soc. 1988, 110, 3747-3754. (b) Simard, M.; Su, D.; Wuest, J. D. Ibid. 1991, 113, 4696-4698. (c) Copp, S. B.; Subramanian, S.; Zaworotko, M. J. Ibid. 1992, 114, 8719-8720. (d) Reddy, D. S.; Craig, D. C.; Rae, A. D.; Desiraju, G. R. J. Chem. Soc., Chem. Commun. 1993, 1737-1739. (e) Zaworotko, M. J. Chem. Soc. Rev. 1994, 23, 283-288. (f) Batten, S. R.; Hoskins, B. F.; Robson, R. J. Am. Chem. Soc. 1995, 117, 5385-5386. (g) Fujita, M.; Kwon, Y. J.; Sasaki, O.; Yamaguchi, K.; Ogura, K. Ibid. 1995, 117, 7287-7288.
7. (a) See, for example: (a) Ermer, O. J. Am. Chem. Soc. 1988, 110, 3747-3754. (b) Simard, M.; Su, D.; Wuest, J. D. Ibid. 1991, 113, 4696-4698. (c) Copp, S. B.; Subramanian, S.; Zaworotko, M. J. Ibid. 1992, 114, 8719-8720. (d) Reddy, D. S.; Craig, D. C.; Rae, A. D.; Desiraju, G. R. J. Chem. Soc., Chem. Commun. 1993, 1737-1739. (e) Zaworotko, M. J. Chem. Soc. Rev. 1994, 23, 283-288. (f) Batten, S. R.; Hoskins, B. F.; Robson, R. J. Am. Chem. Soc. 1995, 117, 5385-5386. (g) Fujita, M.; Kwon, Y. J.; Sasaki, O.; Yamaguchi, K.; Ogura, K. Ibid. 1995, 117, 7287-7288.
8. (a) See, for example: (a) Ermer, O. J. Am. Chem. Soc. 1988, 110, 3747-3754. (b) Simard, M.; Su, D.; Wuest, J. D. Ibid. 1991, 113, 4696-4698. (c) Copp, S. B.; Subramanian, S.; Zaworotko, M. J. Ibid. 1992, 114, 8719-8720. (d) Reddy, D. S.; Craig, D. C.; Rae, A. D.; Desiraju, G. R. J. Chem. Soc., Chem. Commun. 1993, 1737-1739. (e) Zaworotko, M. J. Chem. Soc. Rev. 1994, 23, 283-288. (f) Batten, S. R.; Hoskins, B. F.; Robson, R. J. Am. Chem. Soc. 1995, 117, 5385-5386. (g) Fujita, M.; Kwon, Y. J.; Sasaki, O.; Yamaguchi, K.; Ogura, K. Ibid. 1995, 117, 7287-7288.
9. (a) See, for example: (a) Ermer, O. J. Am. Chem. Soc. 1988, 110, 3747-3754. (b) Simard, M.; Su, D.; Wuest, J. D. Ibid. 1991, 113, 4696-4698. (c) Copp, S. B.; Subramanian, S.; Zaworotko, M. J. Ibid. 1992, 114, 8719-8720. (d) Reddy, D. S.; Craig, D. C.; Rae, A. D.; Desiraju, G. R. J. Chem. Soc., Chem. Commun. 1993, 1737-1739. (e) Zaworotko, M. J. Chem. Soc. Rev. 1994, 23, 283-288. (f) Batten, S. R.; Hoskins, B. F.; Robson, R. J. Am. Chem. Soc. 1995, 117, 5385-5386. (g) Fujita, M.; Kwon, Y. J.; Sasaki, O.; Yamaguchi, K.; Ogura, K. Ibid. 1995, 117, 7287-7288.
10. (a) Aoyama, Y.; Endo, K.; Kobayashi, K.; Masuda, H. Supramol. Chem. 1995, 4, 229-241.
11. (b) Endo, K.; Sawaki, T.; Koyanagi, M.; Kobayashi, K.; Masuda, H.; Aoyama, Y. J. Am. Chem. Soc. 1995, 117, 8341-8352.
12. (c) Aoyama, Y.; Endo, K.; Anzai, T.; Yamaguchi, Y.; Sawaki, T.; Kobayashi, K.; Kanehisa, N.; Hashimoto, H.; Kai, Y.; Masuda, H. J. Am. Chem. Soc. 1996, 118, 5562-5571.
13. For a general reference on electronic spectroscopy of organic crystals, see: Pope, M.; Swenberg, C. E. Annu. Rev. Phys. Chem. 1984, 35, 613-655.
14. Fluorescence maxima (nm) for other pattern-m adducts and solid anthracene are 420, 442, 465 (sh), and 500 (sh) (for 1·3a). 414, 438, 460, and 490 (sh) (1·9b), 414, 437, 460, and 490 (sh) (1·9g). and 422, 444, 470, 493 (sh) (solid anthracene) (sh = shoulder).
15. Chandross, E. A.; Ferguson, J. J. Chem. Phys. 1966, 45, 3564-3567.
16. Chandross, E. A. J. Chem. Phys. 1965, 43, 4175-4176.
17. 3, Z = 2, d = 1.225, no. of uniq rflc = 7671, no. of rflc used = 2512, GOF = 1.18, R = 0.040.
18. Apohost 1 dispersed in KBr shows a featureless emission at 446 nm when irradiated at 408 nm.
19. (15) The choice of low temperatures is to minimize dissolution of the host and its adducts. Nevertheless, exchange may involve dissolution and recrystallization; the mechanism of guest-exchange under the solid-liquid conditions has not been established. For related work, see: (a) Wang, X.; Simard, M.; Wuest, J. D. J. Am. Chem. Soc. 1994, 116, 12119-12120 (footnote 16). (b) Reference 4b (footnote 20).
20. The choice of low temperatures is to minimize dissolution of the host and its adducts. Nevertheless, exchange may involve dissolution and recrystallization; the mechanism of guest-exchange under the solid-liquid conditions has not been established. For related work, see: (a) Wang, X.; Simard, M.; Wuest, J. D. J. Am. Chem. Soc. 1994, 116, 12119-12120 (footnote 16). (b) Reference 4b (footnote 20).