Finite molecular assemblies in the organic solid state: toward engineering properties of solids

Advances in Physical Organic Chemistry

Volumn 40, Issue , 2005, Pages 109-152

  Hamilton, Tamara D ^a   MacGillivray, Leonard R ^a  

^a University of Iowa   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33750561838     PISSN: 00653160     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S0065-3160(05)40003-9     Document Type: Review

References (90)

1. Desiraju G.R. Crystal Engineering: The Design of Organic Solids (1989), Elsevier, Amsterdam
2. Desiraju G.R. Angew. Chem., Int. Ed. Engl. 34 (1995) 2311-2327
3. Lawrence D.S., Jiang T., and Levett M. Chem. Rev. 95 (1995) 2229-2260
4. Whitesides G.M., Simanek E.E., Mathias J.P., Seto C.T., Chin D., Mammen M., and Gordon D.M. Acc. Chem. Res. 28 (1995) 37-44
5. Krische M.J., and Lehn J.-M. Struct. Bond. 96 (2000) 1-30
6. Zimmerman S.C., and Corbin P.S. Struct. Bond. 96 (2000) 63-94
7. MacGillivray L.R., and Atwood J.L. Angew. Chem., Int. Ed. 38 (1999) 1018-1033
8. Leiserowitz L. Acta Crystallogr. Sect. B 32 (1976) 775-802
9. Allen F.H., Motherwell W.D.S., Raithby P.R., Shields G.P., and Taylor R. New J. Chem. (1999) 25-34
10. Evans S.V., and Trotter J. Acta Crystallogr. Sect. B 44 (1988) 533-538
11. Fitzgerald L.J., Gallucci J.C., and Gerkin R.E. Acta Crystallogr. Sect. B 47 (1991) 776-782
12. MacGillivray L.R., and Siebke M.M. J. Chem. Crystallogr. 31 (2001) 373-376
13. Ducharme Y., and Wuest J.D. J. Org. Chem. 53 (1988) 5787-5789
14. Gao X., Friščić T., Papaefstathiou G.S., and MacGillivray L.R. J. Chem. Crystallogr. 34 (2004) 371-374
15. Walsh P.W., Maverick E., Chiefari J., and Lightner D.A. J. Am. Chem. Soc. 119 (1997) 3802-3806
16. Alajarin M., López-Lázaro A., Pastor A., Prince P.D., Steed J.W., and Arakawa R. Chem. Commun. (2001) 169-170
17. Beijer F.H., Kooijman H., Spek A.L., Sijbesma R.P., and Meijer E.W. Angew. Chem., Int. Ed. Engl. 37 (1998) 75-78
18. Beijer F.H., Sijbesma R.P., Kooijman H., Spek A.L., and Meijer E.W. J. Am. Chem. Soc. 120 (1998) 6761-6769
19. Jorgensen W.L., and Pranata J. J. Am. Chem. Soc. 112 (1990) 2008
20. Pranata J., Wierschke S.G., and Jorgensen W.L. J. Am. Chem. Soc. 113 (1991) 2810
21. Folmer B.J.B., Sijbesma R.P., Kooijman H., Spek A.L., and Meijer E.W. J. Am. Chem. Soc. 121 (1999) 9001-9007
22. Gong B., Yan Y., Zeng H., Skrzypczak-Jankunn E., Kim Y.W., Zhu J., and Ickes H. J. Am. Chem. Soc. 121 (1999) 5607-5608
23. Davis A.P., Draper S.M., Dunne G., and Ashton P. Chem. Commun. (1999) 2265-2266
24. Etter M.C., and Reutzel S.M. J. Am. Chem. Soc. 113 (1991) 2586-2598
25. Aakeröy C.B., Beatty A.M., and Helfrich B.A. Angew. Chem., Int. Ed. Engl. 40 (2001) 3240-3242
26. Etter M.C. Acc. Chem. Res. 23 (1990) 120-126
27. Aakeröy C.B., Beatty A.M., and Helfrich B.A. J. Am. Chem. Soc. 124 (2002) 14425-14432
28. Mathias J.P., Simanek E.E., Zerkowski J.A., Seto C.T., and Whitesides G.M. J. Am. Chem. Soc. 116 (1994) 4316-4325
29. Yang J., Fan E., Geib S.J., and Hamilton A.D. J. Am. Chem. Soc. 115 (1993) 5314-5315
30. Yang J., Marendaz J.-L., Geib S.J., and Hamilton A.D. Tetrahedron Lett. 35 (1994) 3665-3668
31. Duchamp D.J., and Marsh R.E. Acta Crystallogr. B25 (1969) 5-19
32. Alcala R., and Martinez-Carrera S. Acta Crystallogr. B28 (1972) 1671-1677
33. Smith G., Wermuth U.D., and White J.M. Cryst. Eng. Comm. 5 (2003) 58-61
34. Kraft A., and Fröhlich R. Chem. Commun. (1998) 1085-1086
35. Biradha K., and Zaworotko M.J. J. Am. Chem. Soc. 120 (1998) 6431-6432
36. Ferguson G., Gallagher J.F., Glidewell C., Low J.N., and Scrimgeour S.N. Acta Crystallogr. Sect. C 48 (1992) 1272-1275
37. Jetti R.K.R., Kuduva S.S., Reddy D.S., Xue F., Mak T.C.W., Nangia A., and Desiraju G.R. Tetrahedron Lett. 39 (1998) 913-916
38. Valdés, C., Spitz, U.P., Toledo, L.M., Kubik, S.W. and Rebek Jr., J. (1995). J. Am. Chem. Soc. 117, 12733-12745;
39. Valdés, C., Toledo, L.M., Spitz, U. and Rebek Jr., J. (1996). Chem. Eur. J. 2, 989-991.
40. Mogck O., Paulus E.F., Böhmer V., Thondorf I., and Vogt W. Chem. Commun. (1996) 2533-2534
41. Haino T., Yanase M., and Fukuzawa Y. Angew. Chem., Int. Ed. Engl. 36 (1997) 259-260
42. Haino T., Yanase M., and Fukuzawa Y. Tetrahedron Lett. 38 (1997) 3739-3742
43. Makha M., Hardie M.J., and Raston C.L. Chem. Commun. (2002) 1446-1447
44. Atwood J.L., Barbour L.J., Nichols P.J., Raston C.L., and Sandoval C.A. Chem. Eur. J. 5 (1999) 990-996
45. Chapman R.G., Olovsson G., Trotter J., and Sherman J.C. J. Am. Chem. Soc. 120 (1998) 6252-6260
46. Shivanyuk A., Paulus E.F., and Böhmer V. Angew. Chem., Int. Ed. Engl. 38 (1999) 2906-2909
47. Alajarin M., Pastor A., Orenes R.-A., and Steed J.W. J. Org. Chem. 67 (2002) 7091-7095
48. Ghadiri M.R., Kobayashi K., Granja J.R., Chadha R.K., and McRee D.E. Angew. Chem., Int. Ed. Engl. 34 (1995) 93-95
49. Fleischman S.G., Kuduva S.S., McMahon J.A., Moulton B., Bailey Walsh R.D., Rodriguez-Hornedo N., and Zaworotko M.J. Cryst. Growth Des. 3 (2003) 909-919
50. Feldman K.S., and Campbell R.F. J. Org. Chem. 60 (1995) 1924-1925
51. Schmidt G.M.J. Pure Appl. Chem. 27 (1971) 647-678
52. Boiadjiev S.E., Anstine D.T., Maverick E., and Lightner D.A. Tetrahedron: Asymmetr. 6 (1995) 2253-2270
53. Etter M.C., Urbańczyk-Lipkowska Z., Jahn D.A., and Frye J.S. J. Am. Chem. Soc. 108 (1986) 5871-5876
54. Mascal M., Hext N.M., Warmuth R., Moore M.H., and Turkenburg J.P. Angew. Chem., Int. Ed. Engl. 35 (1996) 2203-2206
55. Grossman R.B., Hattori K., Parkin S., Partick B.O., and Varner M.A. J. Am. Chem. Soc. 124 (2002) 13686-13687
56. Weber E., Dörpinghaus N., and Csöregh I. J. Chem. Soc. Perkin Trans. 2 (1990) 2167-2177
57. Biradha K., and Mahata G. Cryst. Growth Des. 5 (2005) 61-63
58. Atwood J.L., Barbour L.J., and Jerga A. Science 296 (2002) 2367-2369
59. Timmerman P.T., Vreekamp R.H., Hulst R., Verboom W., Reinhoudt D.N., Rissanen K., Udachin K.A., and Ripmeester J. Chem. Eur. J. 3 (1997) 1823-1832
60. Rose K.N., Barbour L.J., Orr G.W., and Atwood J.L. Chem. Commun. (1998) 407-408
61. Murayama K., and Aoki K. Chem. Commun. (1998) 607-608
62. Aoki K., Nagae T., Matsubara R., and Fujisawa I. Chem. Lett. 33 (2004) 1264-1265
63. Shivanyuk A., Rissanen K., and Kolehmainen E. Chem. Commun. (2000) 1107-1108
64. Shivanyuk A., Friese J.C., Döring S., and Rebek Jr. J. J. Org. Chem. 68 (2003) 6489-6496
65. Shivanyuk A., Paulus E.F., Rissanen K., Kolehmainen E., and Böhmer V. Chem. Eur. J. 7 (2001) 1944-1951
66. Kobayashi K., Shirasaka T., Yamaguchi K., Sakamoto S., Horn E., and Furukawa N. Chem. Commun. (2000) 41-42
67. MacGillivray L.R., Diamante P.R., Reid J.L., and Ripmeester J.A. Chem. Commun. (2000) 359-360
68. Ma B.-Q., Zhang Y., and Coppens P. Cryst. Growth Des. 1 (2001) 271-275
69. Cave G.W.V., Hardie M.J., Roberts B.A., and Raston C.L. Eur. J. Org. Chem. (2001) 3227-3231
70. Atwood J.L., Barbour L.J., and Jerga A. Proc. Nat. Acad. Sci. USA 99 (2002) 4837-4841
71. Johnson D.W., Hof F., Iovine P.M., Nuckolls C., and Rebek Jr. J. Angew. Chem., Int. Ed. Engl. 41 (2002) 3793-3796
72. Field J.E., Combariza M.Y., Vachet R.W., and Venkataraman D. Chem. Commun. (2002) 2260-2261
73. MacGillivray L.R., and Atwood J.L. Nature 389 (1997) 469-472
74. Gerkensmeier, T., Iwanek, W., Agena, C., Frölich, R., Kotila, S., Näther, C. and Mattay, J. (1999). Eur. J. Org. Chem. 2257-2262
75. Gao X., Friščić T., and MacGillivray L.R. Angew. Chem., Int. Ed. 43 (2004) 232-235
76. Friščić, T. and MacGillivray, L.R. (2003). Chem. Commun. 1306-1307;
77. MacGillivray L.R. Cryst. Eng. Commun. 4 (2002) 37-42
78. Varshney, D.B., Papaefstathiou, G.S. and MacGillivray, L.R. Chem. Commun. 1964-1965;
79. MacGillivray L.R., Reid J.L., Ripmeester J.A., and Papaefstathiou G.S. Indust. Eng. Chem. Res. 41 (2002) 4494-4497
80. Papaefstathiou, G.S., Kipp, A.J. and MacGillivray, L.R. (2001). Chem. Commun. 2432-2433;
81. MacGillivray L.R., Reid J.L., and Ripmeester J.A. J. Am. Chem. Soc. 122 (2000) 7817-7818
82. Ito Y., Borecka B., Trotter J., and Scheffer J.R. Tetrahedron Lett. 36 (1995) 6083-6086
83. Amirakis D.G., Garcia-Garibay M.A., Rowan S.J., Stoddart J.F., White A.J.P., and Williams D.J. Angew. Chem., Int. Ed. 40 (2001) 4256-4261
84. Phba S., Hosomi H., and Ito Y. J. Am. Chem. Soc. 123 (2001) 6349-6352
85. Shan N., and Jones W. Tetrahedron Lett. 44 (2003) 3687-3689
86. Caronna T., Liantonio R., Logothetis T.A., Metrangolo P., Pilati T., and Resnati G. J. Am. Chem. Soc. 126 (2004) 4500-4501
87. Hamilton T.D., Papaefstathiou G.S., and MacGillivray L.R. J. Am. Chem. Soc. 124 (2002) 11606-11607
88. Nicolaou K.C., Vourloumis D., Winssinger N., and Baran P.S. Angew. Chem., Int. Ed. Engl. 39 (2000) 44
89. Balzani V., Gómez-López M., and Stoddart J.F. Acc. Chem. Res. 31 (1998) 405-414
90. POV-ray. Computer program for creating 3D graphics. POV-team™, 2002