Self-assembly of pentaphenol adducts: Formation of 3D network and ladder-type supramolecular structures in the solid state

Crystal Growth and Design

Volumn 6, Issue 3, 2006, Pages 636-642

  Jayaraman, Akhila ^a   Balasubramaniam, Venkataramanan ^a   Valiyaveettil, Suresh ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33645292584     PISSN: 15287483     EISSN: None     Source Type: Journal    
DOI: 10.1021/cg050250x     Document Type: Article

References (72)

1. (a) Lehn, J.-M. Supramolecular Chemistry, Concepts and Perspectives; VCH: Weinheim, 1995.
2. (b) Steed, J. W.; Atwood, J. L. Supramolecular Chemistry; Wiley: New York, 2000.
3. (a) Etter, M. C. Acc. Chem. Res. 1990, 23, 120.
4. (b) Steiner, T. Angew. Chem., Int. Ed. 2002, 41, 48.
5. Desiraju, G. R. Acc. Chem. Res. 2002, 35, 565.
6. Desiraju, G. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 2311.
7. (a) Aakeröy, C. B.; Seddon, K. R. Chem. Soc. Rev. 1993, 22, 397.
8. (b) Subramanian, S.; Zawarotko, M. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2127.
9. Hosseini, M. W. Acc. Chem. Res. 2005, 38, 313.
10. (a) Desiraju, G. R. Acc. Chem. Res. 1996, 29, 441.
11. (b) Steiner, T.; Desiraju, G. R. Chem. Commun. 1998, 891.
12. Desiraju, G. R. Science 1997, 278, 404.
13. (a) Guo, F.; Guo, W. S.; Toda, F. CrystEngComm 2003, 45.
14. (b) Nishio, M. CrystEngComm 2004, 130.
15. Desiraju, G. R.; Steiner, T. The Weak Hydrogen Bond in Structural Chemistry and Biology; Oxford University Press: Oxford, 1999.
16. Czugler, M.; Báthori, N. CrystEngComm 2004, 6, 494.
17. (a) Larson, K.; Öhrström, L. CrystEngComm 2004, 6, 354.
18. (b) Blatov, V. A.; Carlucci, L.; Ciani, G.; Proserpio, D. M. CrystEngComm 2004, 6, 377.
19. Batten, S. R.; Robson, R. Angew Chem., Int. Ed. 1998, 37, 1461.
20. Zhao, X.; Chang, Y.-L.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1990, 112, 6627.
21. (a) Zerkowski, J. A.; Seto, C. T.; Wierda, D. A.; Whitesides, G. M. J. Am. Chem. Soc. 1990, 112, 9025.
22. (b) Zaman, M. B.; Tomura, M.; Yamashita, Y. Acta Crystallogr., Sect. C 2001, 57, 621.
23. Arora, K. K.; Pedireddi, V. R. J. Org. Chem. 2003, 68, 9177.
24. Sly, J.; Peter, K.; Gomer-Nadal, E.; Rovira, C.; Gorriz, L.; Thodarson, P.; Amabilino, D. B.; Rowan, A. E.; Nolte, R. J. M. Chem. Commun. 2005, 1225.
25. (e) Zerkowski, J. A.; MacDonald, J. C.; Seto, C. T.; Wierda, D. A.; Whitesides, G. M. J. Am. Chem. Soc. 1994, 116, 2382.
26. (a) Kimbara, C. K.; Hashimoto, Y.; Sukewaga, M.; Nohira, H.; Saigo, K. J. Am. Chem. Soc. 1996, 18, 3441.
27. (b) Morita, Y.; Fukui, K.; Suzuki, S.; Aoki, T.; Nakazawa, S.; Tamaki, K.; Fuyuhiro, A.; Yamamto, K.; Sato, K.; Shiomi, D.; Naito, A.; Takui, T.; Nakasuji, K. Polyhedron 2003, 22, 2199.
28. (a) Das, A. K.; Haldar, D.; Hegde, R. P.; Shamala, N.; Banerjee, A. Chem. Commun. 2005, 1836.
29. (b) Koshima, S.; Honke, S. J. Org. Chem. 1999, 64, 790.
30. Perkins, D. F.; Lindoy, L. F.; Meehan, G. V.; Turner, P. Chem. Commun. 2004, 152.
31. Herradón, B.; Montero, A.; Mann, E.; Maestro, M. A. CrystEngComm 2004, 6, 513.
32. (a) Aitipamula, S.; Nangia, A.; Thaimattam, R.; Jaskólski, M. Acta Crystallogr. Sect. C 2003, 59, 481.
33. (b) Aitipamula, S.; Desiraju, G. R.; Jaskólski, M.; Nangia, A.; Thaimattam, R. CrystEngComm 2003, 5, 447.
34. Vishweshwar, P.; Nangia, A.; Lynch, V. M. CrystEngComm 2003, 5, 164.
35. (a) Aitipamula, S.; Thallapally, P. K.; Thaimattam, R.; Jaskólski, M.; Desiraju, G. R. Org. Lett. 2002, 6, 921.
36. (b) Reddy, D. S.; Dewa, T.; Endo, K.; Aoyama, Y. Angew. Chem., Int. Ed. 2000, 39, 4266.
37. (a) Tanaka, T.; Tasaki, T.; Aoyama, Y. J. Am. Chem. Soc. 2002, 124, 12453.
38. (b) Thallapally, P. K.; Katz, A. K.; Carrell, H. L.; Desiraju, G. R. Chem. Commun. 2002, 344.
39. Ferguson, G.; Bell, W.; Couper, P. I.; Glidewell, C. Acta Crystallogr. Sect. B 1997, 53, 534.
40. (a) Bishop, R.; Craig, D. C.; Nguyen, Vi T.; Scudder, M. L. Aust. J. Chem. 2001, 54, 637.
41. (b) Nguyen, V. T.; Ahn, P. D.; Bishop, R.; Scudder, M. L.; Craig, D. C. Eur. J. Org. Chem. 2001, 4489.
42. (a) Ung, A. T.; Bishop, R.; Craig, D. C.; Dance, I. G.; Scudder, M. L. J. Chem. Soc., Perkin Trans. 2 1992, 861.
43. (b) Kim, S.; Bishop, R.; Craig, D. C.; Dance, I. G.; Scudder, M. L. J. Org. Chem. 2002, 67, 3221.
44. Yue, W.; Bishop, R.; Craig, D. C.; Scudder, M. L. CrystEngComm 2002, 4, 591.
45. Brock, C. P.; Duncan, L. L. Chem. Mater. 1994, 6, 1307.
46. (a) Corradi, E.; Meille, S. V.; Messina, M. T.; Metrangolo, P.; Resnati, G. Angew. Chem., Int. Ed. 2000, 39, 1782.
47. (b) Papaefstathiou, G. S.; MacGillivray, L. R. Org. Lett. 2001, 3, 3835.
48. MacGillivray, L. R.; Reid, J. L.; Ripmeester, J. A. J. Am. Chem. Soc. 2000, 122, 7817.
49. Biradha, K.; Zaworotko, M. J. J. Am. Chem. Soc. 1998, 120, 6431.
50. (e) Ermer, O.; Eling, A. J. Chem. Soc., Perkin Trans. 2 1994, 925.
51. (f) Gao, X.; Friscic, T.; MacGillivray, L. R. Angew. Chem., Int. Ed. 2004, 43, 232.
52. (g) Biradha, K.; Mahata, G. Cryst. Growth Des. 2005, 5, 61.
53. (h) Zeng, Q.; Wu, D.; Liu, C.; Ma, H.; Lu, J.; Xu, S.; Li, Y.; Wang, C.; Bai, C. Cryst. Growth Des. 2005, 5, 1041.
54. (a) Nguyen, T. L.; Scott, A.; Dinkelmeyer, B.; Fowler, F. W.; Laugher, J. W. New J. Chem. 1998, 22, 129.
55. (b) Zakaria, C. M.; Ferguson, G.; Lough, A. J.; Glidewell, C. Acta Crystallogr. Sect. C 2002, 58, o1.
56. Huang, K.-S.; Britton, D.; Etter, M. C.; Byrn, S. R. J. Mater. Chem. 1997, 7, 713.
57. (a) Ferguson, G.; Glidewell, C.; Lough, A. J.; McManus, G. D.; Meehan, P. R. J. Mater. Chem. 1998, 8, 2339.
58. (b) MacGillivray, L. R.; Reid, J. L.; Ripmeester, J. A. CrystEngComm 1999, 1, 1.
59. Scott, J.; Asami, M.; Tanaka, K. New J. Chem. 2002, 26, 1822.
60. Hoger, S.; Morrison, D. L.; Enkelman, V. J. Am. Chem. Soc. 2002, 124, 6734.
61. (e) Caira, M. R.; Horne, A.; Nassimbeni, L. R.; Toda, F. J. Mater. Chem. 1997, 7, 2145.
62. (f) Ma, B.-Q.; Zhang, Y.; Coppens, P. Cryst. Growth Des. 2002, 2, 7.
63. MacGillivray, L. R. CrystEngComm 2002, 4, 37.
64. Venkataramanan, B.; Ling Guan, W.; Vittal, J. J.; Valiyaveettil, S. Cryst. Growth Des. 2004, 4, 553.
65. SMART and SAINT Software Reference Manuals, Version 6.22; Bruker AXS Analytical X-ray Systems, Inc.: Madison, WI, 2000.
66. Sheldrick, G. M. SADABS, Software for Empirical Absorption Correction; University of Göttingen: Germany, 2000.
67. SHELXTL Reference Manual, Version 5.1; Bruker AXS, Analytical X-ray Systems, Inc.: Madison, WI, 1997.
68. (a) McGaughey, G. B.; Gagné, M.; Rappe, A. K. J. Biol. Chem. 1998, 273, 15458.
69. (b) Narasimhamurthy, T.; Benny, J. C. N.; Pandiarajan, K.; Rathore, R. S. Acta Crystallogr., Sect. C 2003, 59, 620.
70. (a) Noman, A.; Rahman, M. M.; Bishop, R.; Craig, D. C.; Marjo, C. E.; Scudder, M. L. Cryst. Growth Des. 2002, 5, 421.
71. (b) Pedireddi, V. R.; SeethaLekshmi, N.; Tetrahedron Lett. 2004, 45, 1903.
72. Sethuraman, V.; Stanley, N.; Muthaih, P.; Sheldrick, W. S.; Winter, M.; Luger, P.; Weber, M. Cryst. Growth Des. 2003, 5, 823.