Synthesis and solid-state self-assembly of polyphenols

Crystal Growth and Design

Volumn 4, Issue 3, 2004, Pages 553-561

  Venkataramanan, Balasubramaniam ^a   James, Wong Ling Guan ^a   Vittal, Jagadese J ^a   Suresh, Valiyaveettil ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

POLYPHENOL;

ARTICLE; CRYSTAL; CRYSTAL STRUCTURE; CRYSTALLIZATION; HYDROGEN BOND; SOLID; SYNTHESIS;

EID: 2542615125     PISSN: 15287483     EISSN: None     Source Type: Journal    
DOI: 10.1021/cg0341508     Document Type: Article

References (68)

1. (a) Stoddart, J. F.; Tseng, H.-R. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4797.
2. (b) Amirsakis, D. G.; Garcia-Garibay, M. A.; Rowan, S. T.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 2001, 40, 4256.
3. (c) Yang, X.; McBranch, Swanson, B. I.; Li, D. Q. Angew. Chem., Int. Ed. Engl. 1996, 35, 538.
4. (d) Maoz, R.; Matlis, S.; Dimasi, E.; Ocko, B. M.; Sagiv, J. Nature 1996, 384, 150.
5. (a) Jefferey, G. A.; Saenger, W. Hydrogen Bonding in Biological Structures, Springer-Verlag: Berlin, 1991;
6. (b) Whitesides, G. M.; Simanek, E. E.; Mathias, J. P.; Seto, C. T.; Chin, D. N.; Mammen, M.; Gordon, D. M. Acc. Chem. Res. 1995, 28, 37.
7. (c) Gillard, R. E.; Raymo, F. M.; Stoddart, J. F.; Chem. Eur. J. 1997, 3, 1933.
8. (d) Valiyaveettil, S.; Rong Liu, Kum-Fun Mok New J. Chem. 2001, 25, 890.
9. (e) Steiner, T. Angew. Chem., Int. Ed. 2002, 41, 48 and references therein;
10. (f) Desiraju, G. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 2311.
11. (g) Desiraju, G. R. Curr. Opin. Solid State Mater. Sci. 1997, 2, 451.
12. (a) Aitipamula, S.; Nangia, A.; Thaimattam, R.; Jaskólski, M. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 2003, 59, 481.
13. (b) Aitipamula, S.; Desiraju, G. R.; Jaskólski, M.; Nangia, A.; Thaimattam, R. CrystEngComm 2003, 5, 447.
14. (c) Vishweshwar, P.; Nangia, A.; Lynch, V. M. CrystEngComm 2003, 5, 164.
15. (d) Aitipamula, S.; Thallapally, P. K.; Thaimattam, R.; Jaskólski, M.; Desiraju, G. R. Org. Lett. 2002, 6, 921.
16. (e) Thallapally, P. K.; Katz, A. K.; Carrell, H. L.; Desiraju, G. R. Chem. Commun. 2002, 344.
17. (f) Ferguson, G.; Bell, W.; Couper, P. I.; Glidewell, C. Acta Crystallogr., Sect. B: Struct. Sci. 1997, B53, 534.
18. (a) Reddy, D. S.; Dewa, T.; Endo, K, Aoyama, Y. Angew. Chem., Int. Ed. 2000, 39, 4266.
19. (b) Tanaka, T.; Tasaki, T.; Aoyama, Y. J. Am. Chem. Soc. 2002, 124, 12453.
20. (a) Bishop, R.; Craig, D. C.; Nguyen, Vi T.; Scudder, M. L. Aust. J. Chem. 2001, 54, 637.
21. (b) Nguyen, Vi T.; Ahn, P. D.; Bishop, R.; Scudder, M. L.; Craig, D. C. Eur. J. Org. Chem. 2001, 4489.
22. (a) Ahn, P. D.; Bishop, R.; Craig, D. C.; Scudder, M. L. Struct. Chem. 1999, 10(3).
23. (b) Ung, A. T.; Bishop, R.; Craig, D. C.; Dance, I. G.; Scudder, M. L. J. Chem. Soc., Perkin Trans. 2 1992, 861.
24. (c) Kim, S.; Bishop, R.; Craig, D. C.; Dance, I. G.; Scudder, M. L. J. Org. Chem. 2002, 67, 3221.
25. (d) Yue, W.; Bishop, R.; Craig, D. C.; Scudder, M. L. CrystEngComm 2002, 4, 591.
26. (e) Brock, C. P.; Duncan, L. L. Chem. Mater. 1994, 6, 1307.
27. Fournier, J.-H.; Maris, T.; Simard, M.; Wuest, J. D. Cryst. Growth Des. 2003, 3, 535.
28. (a) Tsai, C. J.; Jordan, K. D. Chem. Phys. 1993, 99, 6957.
29. (b) Tsai, C. J.; Jordan, K. D. Chem. Phys. Lett. 1993, 213, 181.
30. (c) Liu, K.; Brown, M. G.; Carter, C.; Saykally, R. J.; Gregory, J. K.; Clary, D. C. Nature 1996, 381, 501, 5886.
31. (d) Xantheas, S. J. J. Chem. Phys. 1994, 100, 7523.
32. (e) Fredericks, S. Y.; Jordan, K. D.; Zwier, T. S. J. Chem. Phys. 1996, 100, 7810.
33. (f) Gruenloh, C. J. Science 1997, 276, 1678.
34. (g) Cruzan, J. D. Science 1996, 271, 59.
35. (h) Liu, K.; Brown, M. G.; Saykally, R. J. J. Phy. Chem. A 1997, 48, 9011.
36. (i) Liu, K.; Brown, M. G.; Saykally, R. J. J. Phys. Chem. A 1997, 48, 8995.
37. (j) Barbour, L. J.; Orr, G. W.; Atwood, J. L. Nature 1998, 393, 671.
38. (k) Kamb, B. Acta Crystallogr. 1964, 17, 1437.
39. (a) Blanton, W. B.; Gordon-Wylie, S. W.; Clark, G. R.; Jordan, K. D.; Wood, J. T.; Geoser, U.; Collins, T. J. J. Am. Chem. Soc. 1999, 121, 3551.
40. (b) Barbour, L. J.; Orr, G. W.; Atwood, J. L. Chem. Commun. 2000, 859.
41. (c) Atwood, J. L.; Barbour, L. J.; Ness, T. J.; Raston, C. L.; Rastonm, P. L. J. Am. Chem. Soc. 2001, 123, 7192.
42. (d) Doedens, R. J.; Yohannes, E.; Khan, M. I. Chem. Commun. 2002, 62.
43. (e) Buck, U.; Ettischer, I.; Melzer, M.; Buch, V.; Sadle, J. Phys. Rev. Lett. 1998, 80, 2578.
44. (f) Nauta, K.; Miller, R. E. Science 2000, 287, 293.
45. (g) Ludwig, R. Angew. Chem., Int. Ed. 2001, 40, 1808 and references therein.
46. Pugliano, N.; Saykally, R. J. Science 1992, 257, 1937.
47. (a) Supriya, S.; Das, S. K. New J. Chem. 2003, 27, 1568.
48. (b) Cruzan, J. D.; Braly, L. B.; Liu, K.; Brown, M. G.; Loeser, J. G.; Saykally, R. J. Science 1996, 271, 59.
49. Liu, K, Brown, M. G.; Cruzan, J. D.; Saykally, R. J. Science 1996, 271, 62.
50. (a) Gregory, J. K.; Clary, D. C.; Liu, K.; Brown, M. G.; Saykally, R. J. Science 1997, 275, 814.
51. (b) Weinhold, F. J. Chem. Phys. 1998, 109, 367-372.
52. (a) Eisenberg, D.; Kauzmann, W. The Structure and Properties of Water; Oxford University Press: Oxford, 1969;
53. (b) Fletcher, N. H. The Chemical Physics of Ice; Cambridge University Press: Cambridge, 1970.
54. (a) Speedy, R. J.; Madura, J. D.; Jørgensen, W. L. J. Phys. Chem. 1987, 91, 909.
55. (b) Belch, A. C.; Rice, S. A. J. Chem. Phys. 1987, 86, 5676.
56. (a) Custelcean, R.; Afloroaei, C.; Vlassa, M.; Polverejan, A. Angew. Chem., Int. Ed. 2000, 39, 3094.
57. (b) Moorthy, J. N.; Natarajan, R.; Venugopalan, P. Angew. Chem., Int. Ed. 2002, 41, 3417.
58. (c) Pal, S.; Sankaran, N. B.; Samanta, A. Angew. Chem., Int. Ed. 2003, 42, 1741.
59. (a) Infantes, L.; Chisholm, J.; Motherwell, S. CrystEngComm 2003, 5, 480.
60. (b) Infantes, L.; Motherwell, S. CrystEngComm 2002, 4, 454.
61. (a) Feng, Z.; Fan, A.; Valiyaveettil, S.; Vittal, J. J. Cryst. Growth Des. 2003, 3, 555.
62. (b) Liu, R.; Valiyaveettil, S.; Mok, K. F.; Vittal, J. J.; Hoong, A. K. M. CrystEngComm 2002, 4, 574.
63. SMART and SAINT Software Reference Manuals, Version 6.22, Bruker AXS Analytical X-ray Systems, Inc., Madison, WI, 2000.
64. Sheldrick, G. M., SADABS, Software for Empirical Absorption Correction, University of Göttingen, Germany, 2000.
65. SHELXTL Reference Manual, Version 5.1, Bruker AXS Analytical X-ray Systems, Inc., Madison, WI, 1997.
66. Barberá, J.; Iglesias, R.; Serrano, J. L.; Sierra, T.; De La Fuente, M. R.; Palacios, B.; Pérez-Jubindo, M. A.; Vázquez, J, T. J. Am. Chem. Soc. 1998, 120, 2908.
67. Tückmantel, W.; Kozikowski, P. A.; Romanczyk, J. L. Jr. J. Am. Chem. Soc. 1999, 121, 12073.
68. Kelderman, K.; Starmans, W. A. J.; van Duynhoven, J. P. M.; Verboom, W.; Engbersen, J. F. J.; Reinhoudt, D. N. Chem. Mater. 1994, 6, 412.