Anion-Binding Macrocycles

Modern Supramolecular Chemistry: Strategies for Macrocycle Synthesis

Volumn , Issue , 2008, Pages 315-347

  Katayev, Evgeny A ^a   Melfi, Patricia J ^b   Sessler, Jonathan L ^b  

^a A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

^b UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

Anion binding macrocycles; Ditopic receptors; Macrocycle 55; Macrocycle H2SO4 53; Modern supramolecular chemistry; Receptors for ion pairs; Receptors with different binding sites

Indexed keywords

EID: 84891299057     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527621484.ch9     Document Type: Chapter

References (126)

1. Bianchi, A., Bowman-James, K. and Garcia-Espaňa, E. (1997) Supra-molecular Chemistry of Anions, Wiley-VCH, New York.
2. Sessler, J.L., Gale, P.A. and Cho, W.-S. (2006) Anion Receptor Chemistry, in Monographs in Supramolecular Chemistry (ed.Stoddart, J.F.) Royal Society of Chemistry, Cambridge.
3. Gunnlaugsson, T., Glynn, M., Tocci, G.M., Kruger, P.E. and Pfeffer, F.M. (2006) Coord. Chem. Rev., 250, 30943117.
4. Nguyen, B.T. and Anslyn, E.V. (2006) Coord. Chem. Rev., 250, 3118-3127.
5. Martínez-Máňez, R. and Sancenón, F. (2006) Coord. Chem. Rev., 250, 30813093.
6. Gale, P.A. and Quesada, R. (2006) Coord. Chem. Rev., 250, 3219-3244.
7. Llinares, J.M., Powell, D. and Bowman-James, K. (2003) Coord. Chem. Rev., 240, 57-75.
8. Hosseini, M.W. (2003) Coord. Chem. Rev., 240, 157-166.
9. Bowman-James, K. (2005) Acc. Chem. Res., 38, 671-676.
10. Kang, S.O., Begum, R.A. and Bowman-James, W. (2006) Angew. Chem., 118, 8048-8061; Angew. Chem. Int. Ed., 45, 7882-7894.
11. Wichmann, K., Antonioli, B., Söhnel, T., Wenzel, M., Gloe, K., Price, J.R., Lindoy, L.F., Blake, A.J. and Schröder, M. (2006) Coord. Chem. Rev., 250, 2987-3003.
12. Bondy, C.R. and Loeb, S.J. (2003) Coord. Chem. Rev., 240, 77-99.
13. Kang, S.O., Hossain, Md.A. and Bowman-James, K. (2006) Coord. Chem. Rev., 250, 3038-3052.
14. Best, M.D., Tobey, S.L. and Anslyn, E.V. (2003) Coord. Chem. Rev., 240, 3-15.
15. Schmuck, C. (2006) Coord. Chem. Rev., 250, 3053-3067.
16. Yoon, J., Kim, S.K., Singh, J. and Kim, K. S. (2006) Chem. Soc. Rev., 35, 355-360.
17. Davis, A.P. and Joos, J.-B. (2003) Coord. Chem. Rev., 240, 143-156.
18. Sessler, J.L. and Davis, J.M. (2001) Acc. Chem. Res., 34, 989-997.
19. Sessler, J.L., Camilolo, S. and Gale, P.A. (2003) Coord. Chem. Rev., 240, 17-55.
20. Beer, P.D. and Hays, E.J. (2003) Coord. Chem. Rev., 240, 167-189.
21. Severin, K. (2006) Chem. Commun.., 3859-3867.
22. Severin, K. (2006) "Synthetic Organometallic Hosts for Biologically Interesting Molecules'' in Bioorganometallic Chemistry (Topics in Organometallic Chemistry) (ed. Simonneaux, G.), Springer, Heidelberg, 123-142.
23. Martinez-Máňez, R. and Sancenón, F. (2003) Chem. Rev., 103, 4419-4476.
24. Callan, J.F., Prasanna de Silva, A. and Magri, D.C. (2005) Tetrahedron, 61, 8551-8588.
25. Katayev, E.A., Ustynyuk, Y.A. and Sessler, J.L. (2006) Coord. Chem. Rev., 250, 3004-3037.
26. Lankshear, M.D. and Beer, P.D. (2006) Coord. Chem. Rev., 250, 3142-3160.
27. Gimeno, N. and Vilar, R. (2006) Coord. Chem. Rev., 250, 3161-3189.
28. Mahoney, J.M., Beatty, A.M. and Smith, B.D. (2001) J. Am. Chem. Soc., 123, 5847-5848.
29. Mahoney, J.M., Davis, J.P., Beatty, A.M. and Smith, B.D. (2003) J. Org. Chem., 68, 9819-9820.
30. Mahoney, J.M., Marshall, R.A., Beatty, A.M., Smith, B.D., Camiolo, S. and Gale, P.A. (2001) J. Supramol. Chem., 1, 289-292.
31. Koulov, A.V., Mahoney, J.M., Beatty, A.M. and Smith, B.D. (2003) Org. Biomol. Chem., 1, 27-29.
32. Mahoney, J.M., Nawaratna, G.U., Beatty, A.M., Duggan, P.J. and Smith, B.D. (2004) Inorg. Chem., 43, 5902-5907.
33. Mahoney, J.M., Beatty, A.M. and Smith, B.D. (2004) Inorg. Chem., 43, 7617-7621.
34. Mahoney, J.M., Stucker, K.A., Jiang, H., Carmichael, I., Brinkmann, N.R., Beatty, A.M., Noll, B.C. and Smith, B.D. (2005)J.Am. Chem. Soc., 127,2922-2928.
35. Gunning, P., Benniston, A.C. and Peacock, R.D. (2004) Chem. Commun., 2226-2227.
36. Benniston, A.C., Gunning, P. and Peacock, R.D. (2005) J. Org. Chem., 70, 115-123.
37. Gunning, P.T. (2005) Org. Biomol. Chem., 3, 3877-3879.
38. Jencks, W.P. (1981) Proc. Natl. Acad. Sci. U.S.A., 78, 4046-4050.
39. Suksai, C., Leeladee, P., Jainuknan, D., Tuntulani, T., Muangsin, N., Chailapakul, O., Kongsaeree, P. and Pakavatchai, C. (2005) Terahedron. Lett., 46, 2765-2769.
40. Mathews, S.E. and Beer, P.D. (2005) Supramol. Chem., 17, 411-435.
41. Lhotak, P. (2005) "Anion Receptors Based on Calixarenes" in Anion Sensing, (Topics in Current Chemistry) (ed. Stibor, J.), Springer, Heidelberg, 255, 65-95.
42. Morzherin, Y., Rudkevich, D.M., Verboom, W. and Reinhoudt, D.N. (1993) J. Org.Chem., 58, 7602-7605.
43. Cameron, B.R. and Loeb, S.J. (1997) Chem. Commun., 573-574.
44. Sansone, F., Baldini, L., Casnati, A., Lazzarotto, M., Ugozzoli, F. and Ungaro, R. (2002) Proc. Natl. Acad. Sci. U.S.A., 99, 4842-4844.
45. Miao, R., Zheng, Q.-Y., Chen, C.-F. and Huang, Z.-T. (2005) Tetrahedron Lett., 46, 2155-2158.
46. Casnati, A., Pirondini, L., Pelizzi, N. and Ungaro, R. (2000) Supramol. Chem., 12, 53-65.
47. Casnati, A., Fochi, M., Minari, P., Pochini, A., Reggiani, M. and Ungaro, R. (1996) Gazz. Chim. Ital., 126, 99-102.
48. Gale, P.A. (1998) Tetrahedron Lett., 39, 3873-3876.
49. Camiolo, S., Gale, P.A., Ogden, M.I., Skelton, B.W. and White, A.H. (2001) J. Chem. Soc. Perkin Trans., 2, 1294-1298.
50. Camiolo, S., Gale, P.A., Light, M.E. and Hursthouse, M.B. (2001) Supramol. Chem., 13, 613-615.
51. Kim, S.K., Kang, B.-G., Koh, H.S., Yoon, Y.J., Jung, S.J., Jeong, B., Lee, K.-D. and Yoon, J. (2004) Org. Lett., 6, 4655-4658.
52. Sebo, L., Schweizer, B. and Diederich, F. (2000) Helv. Chim. Acta, 83, 80-92.
53. Qing, G.-Y., He, Y.-B., Zhao, Y., Hu, C.-C., Liu, S.-Y. and Yang, X. (2006) Eur. J. Org. Chem., 1574-1580.
54. Yang, Y.S., Ko, S.W., Song, I.H., Ryu, B.J. and Nam, K.C. (2003) Bull. Korean Chem. Soc., 24, 681-683.
55. Zlatuskova, P., Stibor, I., Tkadlecova, M. and Lhotak, P. (2004) Tetrahedron, 60, 11383-11390.
56. Tumcharern, G., Tuntulani, T., Coles, S. J., Hursthouse, M.B. and Kilburn, J.D. (2003) Org. Lett., 5, 4971-4974.
57. Kaewtong, C., Fuangswasdi, S., Muangsin, N., Chaichit, N., Vicens, J. and Pulpoka, B. (2006) Org. Lett., 8,1561-1564.
58. Nabeshima, T., Saiki, T., Iwabuchi, J. and Akine, S. (2005) J. Am. Chem. Soc., 127, 5507-5511.
59. Lankshear, M.D., Cowley, A.R. and Beer, P.D. (2006) Chem. Commun., 612-614.
60. Tongraung, P., Chantarasiri, N. and Tuntulani, T. (2003) Tetrahedron Lett., 44, 29-32.
61. Sisson, A.L., Clare, J.P. and Davis, A.P. (2005) Chem. Commun., 5263-5265.
62. Khatri, V.K., Upreti, S. and Pandey, P.S. (2006) Org. Lett., 8, 1755-1758.
63. Davis, A.P., Gilmer, J.F. and Perry, J.J. (1996) Angew. Chem., 108, 1410-1413; Angew. Chem. Int. Ed., 35, 1312-1315.
64. Bhattarai, K.B., Davis, A.P., Perry, J.J., Walter, C.J., Menzer, S. and Williams, D. J. (1997) J. Org. Chem., 62, 8463-8473.
65. Camiolo, S. and Gale, P.A. (2000) Chem. Commun., 1129-1130.
66. Woods, C.J., Camiolo, S., Light, M.E., Coles, S.J., Hursthouse, M.B., King, M. A., Gale, P.A. and Essex, J.W. (2002) J. Am. Chem. Soc., 124, 8644-8652.
67. Anzenbacher, P., Jr. Jursíková, K., Lynch, V.M., Gale, P.A. and Sessler, J.L. (1999) J. Am. Chem. Soc., 121, 11020-11021.
68. Dukh, M., Drasar, P., Cerny, I., Pouzar, V., Shriver, J.A., Král, V. and Sessler, J.L. (2002) Supramol. Chem., 14, 237-244.
69. Miyaji, H., Anzenbacher, P., Jr. Sessler, J.L., Bleasdale, E.R. and Gale, P.A. (1999) Chem. Commun., 1723-1724.
70. Anzenbacher, P., Jr. Jursikova, K. and Sessler, J.L. (2000) J. Am. Chem. Soc., 122, 9350-9351.
71. Nishiyabu, R. and Anzenbacher, P. Jr. (2006) Org. Lett., 8, 359-362.
72. Sessler, J.L., Král, V., Shishkanova, T.V. and Gale, P.A. (2002) Proc. Natl. Acad. Sci. U.S.A., 99, 4848-4853.
73. Sessler, J.L., Gale, P.A. and Genge, J.W. (1998) Chem. Eur. J., 4, 1095-1099.
74. Anzenbacher, P., Jr. Nishiyabu, R. and Palacios, M.A. (2006) Coord. Chem. Rev., 250, 2929-2938.
75. Nishiyabu, R., Palacios, M.A., Dehaen, W. and Anzenbacher, P. Jr. (2006) J. Am. Chem. Soc., 128, 11496-11504.
76. Yoon, D.-W., Hwang, H. and Lee, C.-H. (2002) Angew. Chem., 114, 1835-1837; Angew. Chem. Int. Ed., 41, 1757-1759.
77. Lee, C.-H., Na, H.-K., Yoon, D.-W., Won, D.-H., Cho, W.-S., Lynch, V.M., Shevchuk, S.V. and Sessler, J.L. (2003) J. Am. Chem. Soc., 125, 7301-7306.
78. Lee, C.-H., Lee, J.-S., Na, H.-K., Yoon, D.-W., Miyaji, H., Cho, W.-S. and Sessler, J.L. (2005) J. Org. Chem., 70, 2067-2074.
79. Sessler, J.L., Cyr, M.J., Lynch, V., McGhee, E. and Ibers, J.A. (1990) J. Am. Chem. Soc., 112, 2810-2813.
80. Sessler, J.L., Cyr, M.J. and Burrell, A.K. (1991) SynLett, 127-134.
81. Shionoya, M., Furuta, H., Lynch, V., Harriman, A. and Sessler, J.L. (1992) J. Am. Chem. Soc., 114, 5714-5722.
82. Sessler, J.L., Cyr, M.J., Furuta, H., Král, V., Mody, T., Morishima, T., Shionoya, M. and Weghorn, S. (1993) Pure Appl. Chem., 65, 393-398.
83. Scherer, M., Sessler, J.L., Gebauer, A. and Lynch, V. (1998) Chem. Commun., 85-86.
84. Furuta, H., Cyr, M.J. and Sessler, J.L. (1991) J. Am. Chem. Soc., 113, 6677-6678.
85. Iverson, B.L., Shreder, K., Král, V., Sansom, P., Lynch, V. and Sessler, J.L. (1996) J. Am. Chem. Soc.,118, 1608-1616.
86. Sessler, J.L., Furuta, H. and Král, V. (1993) Supramol. Chem., 1, 209-220.
87. Král, V. and Sessler, J.L. (1995) Tetrahedron, 51, 539-554.
88. Král, V., Andrievsky, A., Sessler, J.L. (1995) J. Chem. Soc., Chem. Commun., 2349-2351.
89. Cormode, D.P., Murray, S.S., Cowley, A. R. and Beer, P.D. (2006) Dalton Trans., 5135-5140.
90. Gong, J. and Gibb, B.C. (2005) Chem. Commun., 1393-1395.
91. Gong, J. and Gibb, B.C. (2005) Chem. Commun., 3319-3321.
92. Beer, P.D., Berry, N., Drew, M.G.B., Fox, O.D., Padilla-Tosta, M.E. and Patell, S., (2001) Chem. Commun., 199-200.
93. Berry, N.G., Pratt, M.D., Fox, O.D. and Beer, P.D. (2001) Supramol. Chem., 13, 677-682.
94. Beer, P.D. and Wallace, W.W.H., (2005) "Sensing, Templation and Self-Assembly by Macrocyclic Ligand Systems" in Macrocyclic Chemistry, Current Trends and Future Perspectives (ed. Gloe, K.) Springer, The Netherlands, pp.105-119.
95. Beer, P.D. and Bayly, S.R. (2005) "Anion Sensing by Metal-Based Receptors", in Topics in Current Chemistry, 255, Springer, Berlin, pp. 125-162.
96. Wong, W.W.H., Curiel, D., Cowley, A.R. and Beer, P.D. (2005) Dalton Trans., 359-364.
97. Webber, P.R.A., Drew, M.G.B., Hibbert, R. and Beer, P.D. (2004) Dalton Trans., 1127-1135.
98. Wong, W.W.H., Phipps, D.E. and Beer, P.D. (2004) Polyhedron, 2821-2829.
99. Beer, P.D., Berry, N.G., Cowley, A.R., Hayes, E.J., Oates, E.C. and Wong, W.W.H. (2003) Chem. Commun., 2408-2409.
100. Beer, P.D., Cheetham, A.G., Drew, M.G.B., Fox, O.D., Hayes, E.J. and Rolls, T.D. (2003) Dalton Trans., 603-611.
101. Galbraith, S.G., Plieger, P.G. and Tasker, P.A. (2002) Chem. Commun., 2662-2663.
102. Miller, H.A., Laing, N., Parsons, S., Parkin, A., Tasker, P.A. and White, D.J. (2000) Dalton Trans., 3773-3782.
103. Plieger, P.G., Tasker, P.A. and Galbraith, S.G. (2004) Dalton Trans., 313-318.
104. Fujita, T. and Lehn, J.-M. (1988) Tetrahedron Lett., 29, 1709-1712.
105. Hossain, M.A., Llinares, J.M., Powell, D. and Bowman-James, K. (2001) Inorg. Chem., 40, 2936-2937.
106. Kang, S.O., Powell, D. and Bowman-James, K. (2005) J. Am. Chem. Soc., 127, 13478-13479.
107. Kang, S.O., Hossain, M.A., Powell, D. and Bowman-James, K. (2005) Chem. Commun., 328-330.
108. Kang, S.O., Powell, D., Day, V.W. and Bowman-James, K. (2006) Angew. Chem., 118, 1955-1959; Angew. Chem. Int. Ed., 45, 1921-1925.
109. Kubik, S., Kirchner, R., Nolting, D. and Seidel, J. (2002) J. Am. Chem. Soc., 124, 12752-12760.
110. Kubik, S., Goddard, R., Otto, S., Pohl, S., Reyheller, C. and Stuwe, S. (2005) Biosens. Bioelectron., 20, 2364-2375.
111. Otto, S. and Kubik, S. (2003) J. Am. Chem. Soc., 125, 7804-7805.
112. Brooks, S.J., Gale, P.A. and Light, M.E. (2006) Chem. Commun., 4344-4346.
113. Hirata, O., Takeuchi, M. and Shinkai, S. (2005) Chem. Commun., 3805-3807.
114. Francesconi, O., Ienco, A., Moneti, G., Nativi, C. and Roelens, S. (2006) Angew. Chem., 118, 6845-6848; Angew. Chem. Int. Ed., 46, 6693-6696.
115. Garcia-Espana, E., Diaz, P., Llinares, J.M. and Bianchi, A. (2006) Coord. Chem. Rev., 250, 2952-2986.
116. Miranda, C., Escarti, F., Lamarque, L., Yunta, M.J.R., Navarro, P., Garcia-Espaňa, E. and Jimeno, M.L. (2004) J. Am. Chem. Soc., 126, 823-833.
117. Sessler, J.L. and Seidel, D. (2003) Angew. Chem., 115, 5292-5333; Angew. Chem. Int. Ed., 42, 5134-5175.
118. Seidel, D., Lynch, V. and Sessler, J.L. (2002) Angew. Chem., 114, 1480-1483; Angew. Chem. Int. Ed., 41, 1422-1425.
119. Sessler, J.L., Katayev, E., Dan Pantos, G. and Ustynyuk, Y.A. (2004) Chem. Commun., 1276-1277.
120. Moyer, B.A. and Singh, R.P. (2004) Fundamentals and Applications of Anion Separations, Kluwer Academic/Plenum Publishers, New York.
121. Sessler, J.L., Katayev, E., Pantos, G.D., Scherbakov, P., Reshetova, M.D., Khrustalev, V.N., Lynch, V.M. and Ustynyuk, Y.A. (2005) J. Am. Chem. Soc., 127, 11442-11446.
122. Katayev, E.A., Pantos, G.D., Reshetova, M.D., Khrustalev, V.N., Lynch, V.M., Ustynyuk, Y.A. and Sessler, J.L. (2005) Angew. Chem., 117, 7552-7556; Angew. Chem. Int. Ed., 44, 7386-7390.
123. Sessler, J.L., Roznyatovskiy, V., Pantos, G.D., Borisova, N.E., Reshetova, M.D., Lynch, V.M., Khrustalev, V.N. and Ustynyuk, Y.A. (2005) Org. Lett., 7, 5277-5280.
124. Fyfe, M.C.T., Glink, P.T., Menzer, S., Stoddart, J.F., White, A.J.P. and Williams, D.J. (1997) Angew. Chem., 109, 2158-2160; Angew. Chem., Int. Ed. Engl., 36, 2068-2070.
125. Beer, P., Sambrook, M.R. and Curiel, D. (2006) Chem. Commun., 2105-2177.
126. Ng, K.-Y., Cowley, A.R. and Beer, P.D. (2006) Chem. Commun., 3676-3678.