Hydrogen-bonded aryl amide macrocycles: Synthesis, single-crystal structures, and stacking interactions with fullerenes and coronene

Journal of Organic Chemistry

Volumn 73, Issue 5, 2008, Pages 1745-1751

  Zhu, Yuan Yuan ^a   Li, Chuang ^a   Li, Guang Yu ^a   Jiang, Xi Kui ^a   Li, Zhan Ting ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CHLORINE COMPOUNDS; FULLERENES; HYDROGEN BONDS; SINGLE CRYSTALS; SYNTHESIS (CHEMICAL);

ARYL AMIDE MACROCYCLES; STACKING INTERACTIONS;

AMIDES;

AMIDE; CORONENE; FULLERENE DERIVATIVE; MACROCYCLIC COMPOUND;

ARTICLE; COMPLEX FORMATION; CRYSTAL STRUCTURE; DRUG STRUCTURE; DRUG SYNTHESIS; FLUORESCENCE; HYDROGEN BOND; PROTON NUCLEAR MAGNETIC RESONANCE; ULTRAVIOLET SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

AMIDES; CRYSTALLOGRAPHY, X-RAY; FULLERENES; HYDROGEN BONDING; MACROCYCLIC COMPOUNDS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MOLECULAR STRUCTURE; POLYCYCLIC COMPOUNDS; SPECTROMETRY, FLUORESCENCE; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 41149177582     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702046f     Document Type: Article

References (74)

1. (a) Moore, J. S. Acc. Chem. Res. 1997, 30, 402.
2. (b) Grave, C.; Schlüter, A. D. Eur. J. Org. Chem. 2002, 3075.
3. (c) Zhao, D. H.; Moore, J. S. Chem. Commun. 2003, 807.
4. (d) Yamaguchi, Y.; Yoshida, Z.-i. Chem. Eur. J. 2003, 9, 5430.
5. (e) Höger, S. Chem. Eur. J. 2004, 10, 1320.
6. (f) Höger, S. Angew. Chem., Int. Ed. 2005, 44, 3806.
7. (g) Zhang, W.; Moore, J. S. Angew. Chem., Int. Ed. 2006, 45, 4416.
8. (a) Chong, Y. S.; Shimizu, K. D. Synthesis 2002, 1239.
9. (b) MacLachlan, M. J. Pure Appl. Chem. 2006, 78, 873.
10. (c) He, L.; An, Y.; Yuan, L.; Feng, W.; Li, M.; Zhang, D.; Yamato, K.; Zheng, C.; Zeng, X. C.; Gong, B. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 10850.
11. (a) Zhao, D.; Moore, J. S. J. Org. Chem. 2002, 67, 3548.
12. (b) Grave, C.; Lentz, D.; Schaefer, A.; Samori, P.; Rabe, J. P.; Franke, P.; Schlüter, A. D. J. Am. Chem. Soc. 2003, 125, 6907.
13. (c) Odermatt, S.; Alonso-Gomez, J. L.; Seiler, P.; Cid, M. M.; Diederich, F. Angew. Chem., Int. Ed. 2005, 44, 5074.
14. (d) Campbell, K.; Ooms, K. J.; Wasylishen, R. E.; Tykwinski, R. R. Org. Lett. 2005, 7, 3397.
15. (e) Zhang, W.; Brombosz, S. M.; Mendoza, J. L.; Moore, J. S. J. Org. Chem. 2005, 70, 10198.
16. (f) Venturi, M.; Marchioni, F.; Ribera, B. F.; Balzani, V.; Opris, D. M.; Schlüter, A. D. ChemPhysChem 2006, 7, 229.
17. (g) Seo, S. H.; Jones, T. V.; Seyler, H.; Peters, J. O.; Kim, T. H.; Chang, J. Y.; Tew, G. N. J. Am. Chem. Soc. 2006, 128, 9264.
18. (h) Shu, L.; Mayor, M. Chem. Commun. 2006, 4134.
19. (a) Jiang, H.; Léger, J.-M.; Guionneau, P.; Huc, I. Org. Lett. 2004, 6, 2985.
20. (b) Shirude, P. S.; Gillies, E. R.; Ladame, S.; Godde, F.; Shin-ya, K.; Huc, I.; Balasubramanian, S. J. Am. Chem. Soc. 2007, 129, 11890.
21. (a) Yuan, L.; Feng, W.; Yamato, K.; Sanford, A. R.; Xu, D.; Guo, H.; Gong, B. J. Am. Chem. Soc. 2004, 126, 11120.
22. (b) Sanford, A. R.; Yuan, L.; Feng, W.; Yamato, K.; Flowers, R. A.; Gong, B. Chem. Commun. 2005, 4720.
23. (c) Zhang, A.; Han, Y.; Yamato, K.; Zeng, X. C.; Gong, B. Org. Lett. 2006, 8, 803.
24. For reviews on aryl amide foldamers, see: (a) Gong, B. Chem. Eur. J. 2001, 7, 4336.
25. (b) Huc, I. Eur. J. Org. Chem. 2004, 17.
26. (c) Sanford, A.; Yamato, K.; Yang, X. W.; Yuan, L. H.; Han, Y. H.; Gong, B. Eur. J. Biochem. 2004, 271, 1416.
27. (d) Lockman, J. W.; Paul, N. M.; Parquette, J. R. Prog. Polym. Sci. 2005, 30, 423.
28. (e) Li. Z.-T.; Hou, J.-L.; Li, C.; Yi, H.-P. Chem. Asian J. 2006, 1, 766.
29. (a) Hou, J.-L.; Shao, X.-B.; Chen, G.-J.; Zhou, Y.-X.; Jiang, X.-K.; Li, Z.-T. J. Am. Chem. Soc. 2004, 126, 12386.
30. (b) Wu, Z.-Q.; Jiang, X.-K.; Zhu, S.-Z.; Li, Z.-T. Org. Lett. 2004, 6, 229.
31. (c) Zhu, J.; Wang, X.-Z.; Chen, Y.-Q.; Jiang, X.-K.; Chen, X.-Z.; Li, Z.-T. J. Org. Chem. 2004, 69, 6221.
32. (d) Li, C.; Ren, S.-F.; Hou, J.-L.; Yi, H.-P.; Zhu, S.-Z.; Jiang, X.-K.; Li, Z.-T. Angew. Chem., Int. Ed. 2005, 44, 5725.
33. (e) Yi, H.-P.; Chuang Li, C.; Hou, J.-L.; Jiang, X.-K.; Li, Z.-T. Tetrahedron 2005, 61, 7974.
34. (f) Zhu, J.; Lin, J.-B.; Xu, Y.-X.; Shao, X.-B.; Jiang, X.-K.; Li, Z.-T. J. Am. Chem. Soc. 2006, 128, 12307.
35. (g) (i) Yi, H.-P.; Wu, J.; Ding, K.-L.; Jiang, X.-K.; Li, Z.-T. J. Org. Chem. 2007, 72, 870.
36. (h) Li, C.; Wang, G.-T.; Yi, H.-P.; Jiang, X.-K.; Li, Z.-T.; Wang, R.-X. Org. Lett. 2007, 9, 1797.
37. (a) Konishi, T.; Ikeda, A.; Shinkai, S. Tetrahedron 2005, 61, 4881.
38. (b) Boyd, P. D. W.; Reed, C. A. Acc. Chem. Res. 2006, 38, 235.
39. (c) Kawase, T.; Kurata, H. Chem. Rev. 2006, 106, 5250.
40. (d) Tashiro, K.; Aida, T. Chem. Soc. Rev. 2007, 36, 189.
41. Pan, G.-B.; Cheng, X.-H.; Höger, S.; Freyland, W. J. Am. Chem. Soc. 2006, 128, 4218.
42. Li, C.; Zhu, Y.-Y.; Yi, H.-P.; Li, C.-Z.; Jiang, X.-K.; Li, Z.-T.; Yu, Y.-H. Chem. Eur. J. 2007, 13, 9990.
43. An intramolecular hydrogen-bonding, free aryl amide-based macrocyclic receptor for anions has been reported: Choi, K.; Hamilton, A. D. J. Am. Chem. Soc. 2003, 125, 10241.
44. (a) Zhao, X.; Wang, X.-Z.; Jiang, X.-K.; Chen, Y.-Q.; Li, Z.-T.; Chen, G.-J. J. Am. Chem. Soc. 2003, 125, 15128.
45. (b) Zhu, Y.-Y.; Wu, J.; Li, C.; Zhu, J.; Hou, J.-L.; Li, C.-Z.; Jiang, X.-K.; Li, Z.-T. Cryst. Growth Des. 2007, 7, 1490.
46. Doxsee, K. M.; Feigel, M.; Stewart, K. D.; Canary, J. W.; Knobler, C. B.; Cram, D. J. J. Am. Chem. Soc. 1987, 109, 3098.
47. Under the identical conditions, a similar 3 + 3 macrocyclic product was also generated from the reaction of 5 with isophthaloyl dichloride, as evidenced by MALDI-TOF. The attempt of separating this product did not succeed. We thank one of the reviewers for critical comments on this issue.
48. (a) Shimizu, L. S.; Hughes, A. D.; Smith, M. D.; Davis, M. J.; Zhang, B. P.; Zur Loye, H.-C.; Shimizu, K. D. J. Am. Chem. Soc. 2003, 125, 14972.
49. (b) Gibson, S. E.; Lecci, C. Angew. Chem., Int. Ed. 2006, 45, 1364.
50. (c) Pasini, D.; Ricci, M. Curr. Org. Synth. 2007, 4, 59.
51. Hamuro, Y.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1996, 118, 7529.
52. (a) Diederich, F.; Gómez-López, M. Chem. Soc. Rev. 1999, 28, 263.
53. (b) Haino, T.; Yanase, M.; Fukazawa, Y. Angew. Chem., Int. Ed. 1998, 37, 997.
54. (c) Ikeda, A.; Yoshimura, M.; Udzu, H.; Fukuhara, C.; Shinkai, S. J. Am. Chem. Soc. 1999, 121, 4296.
55. (d) Atwood, J. L.; Barbour, L. J.; Heaven, M. W.; Raston, C. L. Angew. Chem., Int. Ed. 2003, 42, 3254.
56. 2 was used for improving the solubility of fullerenes.
57. 1H NMR spectra even in the case of strong complexation, see ref 10 and also: (a) Wang, M.-X.; Zhang, X.-H.; Zheng, Q.-Y. Angew. Chem., Int. Ed. 2004, 43, 838.
58. (b) Gong, H.-Y.; Zhang, X.-H.; Wang, D.-X.; Ma, H.-W.; Zheng, Q.-Y.; Wang, M.-X. Chem. Eur. J. 2006, 12, 9262.
59. (c) Pérez, E. M.; Sierra, M.; Sánchez, L.; Torres, M. R.; Viruela, R.; Viruela, P. M.; Ortí, E.; Martín, N. Angew. Chem., Int. Ed. 2007, 46, 1847.
60. (a) Gafni, A.; Cohen, Y. J. Org. Chem. 1997, 62, 120.
61. (b) Gafni, A.; Cohen, Y. J. Org. Chem. 2002, 67, 2639.
62. (c) Zhao, T.; Beckham, H. W.; Gibson, H. W. Macromolecules 2003, 36, 4833.
63. Wu, J.; Hou, J.-L.; Li, C.; Wu, Z.-Q.; Jiang, X.-K.; Li, Z.-T.; Yu, Y.-H. J. Org. Chem. 2007, 72, 2897.
64. The Benesi-Hildebrand (BH) plots were used to evaluate the association constants, which yielded a 1:1 stoichiometry for all the complexing systems. Applying the titrating data to a 1:2 or 2:1 stoichiometry gave rise to poor results. For the establishment of the 1:1 complexing stoichiometry, see: (a) Benesi, A. H.; Hildebrand, J. H. J. Am. Chem. Soc. 1949, 71, 2703.
65. (b) Abou-Zied, O. K. Spectrochim. Acta A 2005, 62, 245.
66. (a) Martin, N.; Sanchez, L.; Illescas, B.; Perez, I. Chem. Rev. 1998, 98, 2527.
67. (b) Guldi, D. M. Chem. Commun. 2000, 321.
68. (a) Prasanna, M. D.; Row, T. N. G. Cryst. Eng. 2000, 3, 135.
69. (b) Babudri, F.; Farinola, G. M.; Naso, F.; Ragni, R. Chem. Commun. 2007, 1003.
70. (a) Ermer, O.; Neudorft, J. Helv. Chim. Acta 2001, 84, 1268.
71. (b) Yoshizawa, M.; Nakagawa, J.; Kumazawa, K.; Nagao, M.; Kawano, M.; Ozeki, T.; Fujita, M. Angew. Chem., Int. Ed. 2005, 44, 1810.
72. Corbett, P. T.; Leclaire, J.; Vial, L.; West, K. R.; Wietor, J.-L.; Sanders, J. K. M.; Otto, S. Chem. Rev. 2006, 106, 3652.
73. Wang, Q.-C.; Qu, D.-H.; Ren, J.; Chen, K.; Tian, H. Angew. Chem., Int. Ed. 2004, 43, 2661.
74. Wang, X.-B.; Dacres, J. E.; Yang, X.; Broadus, K. M.; Lis, L.; Wang, L.-S.; Kass, S. R. J. Am. Chem. Soc. 2003, 125, 296.