Encapsulation of anions: Macrocyclic receptors based on metal coordination and anion-π interactions

Coordination Chemistry Reviews

Volumn 257, Issue 11-12, 2013, Pages 1716-1727

  Frontera, Antonio ^a  

^a UNIVERSITAT DE LES ILLES BALEARS   (Spain)

Author keywords

Anion interactions; Anions; Heteroaromatic ligands; Molecular architecture; Non covalent interactions; Supramolecular chemistry

Indexed keywords

EID: 84874516040     PISSN: 00108545     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ccr.2013.01.032     Document Type: Review

References (104)

1. Schneider H.-J. Angew. Chem. Int. Ed. 2009, 48:3924-3977.
2. Schneider H.-J., Yatsimirski A. Principles and Methods in Supramolecular Chemistry 2000, Wiley, Chichester.
3. Lehn J.-M. Supramolecular Chemistry. Concepts and Perspectives 1995, Wiley-VCH, Weinheim.
4. Vögtle F. Supramolecular Chemistry: An Introduction 1993, Wiley, New York.
5. Beer P.D., Gale P.A., Smith D.K. Supramolecular Chemistry 1999, Oxford University Press, Oxford.
6. Steed J.W., Atwood J.L. Supramolecular Chemistry 2000, Wiley, Chichester.
7. Meyer E.A., Castellano R.K., Diederich F. Angew. Chem. Int. Ed. 2003, 42:1210-1250.
8. Schneider H.-J., Yatsimirsky A. Chem. Soc. Rev. 2008, 37:263-277.
9. Salonen L.M., Ellermann M., Diederich F. Angew. Chem. Int. Ed. 2011, 50:4808-4842.
10. Müller-Dethlefs K., Hobza P. Chem. Rev. 2000, 100:143-167.
11. Burley S.K., Petsko G.A. Science 1985, 229:23-28.
12. Li S., Cooper V.R., Thonhauser T., Lundqvist B.I., Langreth D.C. J. Phys. Chem. B 2009, 113:11166-11172.
13. Rutledge L.R., Campbell-Verduyn L.S., Wetmore S.D. Chem. Phys. Lett. 2007, 444:167-175.
14. Tsuzuki S., Yoshida M., Uchimaru T., Mikami M. J. Phys. Chem. A 2001, 105:769-773.
15. Ma J.C., Dougherty D.A. Chem. Rev. 1997, 97:1303-1324.
16. Crowley P.B., Golovin A. Proteins Struct. Funct. Genet 2005, 59:231-239.
17. Gallivan J.P., Dougherty D.A. J. Am. Chem. Soc. 2000, 122:870-874.
18. Lamoureux J.S., Maynes J.T., Glover J.N.M. J. Mol. Biol. 2004, 335:399-408.
19. Frey J., Kraus T., Heitz V., Sauvage J.-P. Chem. Commun. 2005, 5310-5312.
20. Masu H., Sakai M., Kishikawa K., Yamamoto M., Yamaguchi K., Kohmoto S. J. Org. Chem. 2005, 70:1423-1431.
21. Bao X., Isaacsohn I., Drew A.F., Smithrud D.B. J. Org. Chem. 2007, 72:3988-4000.
22. Heemstra J.M., Moore J.S. Chem. Commun. 2004, 40:1480-1481.
23. Frontera A., Gamez P., Mascal M., Mooibroek T.J., Reedijk J. Angew. Chem. Int. Ed. 2011, 50:9564-9583.
24. Schottel B.L., Chifotides H.T., Dunbar K.R. Chem. Soc. Rev. 2008, 37:68-83.
25. Caltagirone C., Gale P.A. Chem. Soc. Rev. 2009, 38:520-563.
26. Gamez P., Mooibroek T.J., Teat S.J., Reedijk J. Acc. Chem. Res. 2007, 40:435-444.
27. Hay B.P., Bryantsev V.S. Chem. Commun. 2008, 44:2417-2428.
28. Quiñonero D., Garau C., Rotger C., Frontera A., Ballester P., Costa A., Deyà P.M. Angew. Chem. Int. Ed. 2002, 41:3389-3392.
29. Mascal M., Armstrong A., Bartberger M.D. J. Am. Chem. Soc. 2002, 124:6274-6276.
30. Alkorta I., Rozas I., Elguero J. J. Am. Chem. Soc. 2002, 124:8593-8598.
31. Kim D.Y., Singh N.J., Kim K.S. J. Chem. Theory Comput. 2008, 4:1401-1407.
32. Schottel B.L., Bacsa J., Dunbar K.R. Chem. Commun. 2005, 41:46-47.
33. Han B., Lu J.J., Kochi J.K. Cryst. Growth Des. 2008, 8:1327-1334.
34. Mascal M., Yakovlev I., Nikitin E.B., Fettinger J.C. Angew. Chem. Int. Ed. 2007, 46:8782-8784.
35. Götz R.J., Robertazzi A., Mutikainen I., Turpeinen U., Gamez P., Reedijk J. Chem. Commun. 2008, 44:3384-3386.
36. Albrecht M., Müller M., Mergel O., Rissanen K., Valkonen A. Chem. Eur. J. 2010, 16:5062-5069.
37. Estarellas C., Frontera A., Quiñonero D., Deyà P.M. Angew. Chem. Int. Ed. 2011, 50:415-418.
38. Chakravarty S., Sheng Z.-Z., Iverson B., Moore B. FEBS Lett. 2012, 586:4180-4185.
39. Jenkins D.D., Harris J.B., Howell E.F., Hinde R.J., Baudry J. J. Comput. Chem. 2013, 34:518-522.
40. Dawson R.E., Hennig A., Weimann D.P., Emery D., Ravikumar V., Montenegro J., Takeuchi T., Gabutti S., Mayor M., Mareda J., Schalley C.A., Matile S. Nat. Chem. 2010, 2:533-538.
41. Sakai N., Mareda J., Vauthey E., Matile S. Chem. Commun. 2010, 46:4225-4237.
42. Gale P.A. Chem. Commun. 2011, 47:82-86.
43. Wenzel M., Hiscock J.R., Gale P.A. Chem. Soc. Rev. 2012, 41:480-520.
44. Gale P.A., Quesada R. Coord. Chem. Rev. 2006, 250:3219-3244.
45. Berg J.M. Acc. Chem. Res. 1995, 28:14-19.
46. Ashcroft F.M. Ion Channels and Disease 2000, Academic Press, San Diego and London.
47. Moss B. Chem. Ind. 1996, 407-411.
48. Asakura T., Kim S.-Y., Morita Y., Ozawa M. J. Nucl. Radiochem. Sci. 2005, 6:267-269.
49. Bowman-James K., Bianchi A., Garcia-España E. Anion Coordination Chemistry 2011, Wiley-VCH, Weinheim.
50. Frontera A., Quiñonero D., Deyà P.M. WIREs Comput. Mol. Sci. 2011, 1:440-459.
51. Giese M., Albrecht M., Krappitz T., Peters M., Gossen V., Raabe G., Valkonen A., Rissanen K. Chem. Commun. 2012, 48:9983-9985.
52. Kim D., Tarakeshwar P., Kim K.S. J. Phys. Chem. A 2004, 108:1250-1258.
53. Kim D.Y., Singh N.J., Lee J.W., Kim K.S. J. Chem. Theory Comput. 2008, 4:1162-1169.
54. Garau C., Frontera A., Quiñonero D., Ballester P., Costa A., Deyà P.M. Chem. Phys. Chem. 2003, 4:1344-1348.
55. Quiñonero D., Garau C., Frontera A., Ballester P., Costa A., Deyà P.M. Chem. Phys. Lett. 2002, 359:486-492.
56. Garau C., Quiñonero D., Frontera A., Ballester P., Costa A., Deyà P.M. Org. Lett. 2003, 5:2227-2229.
57. Garau C., Frontera A., Quiñonero D., Ballester P., Costa A., Deyà P.M. J. Phys. Chem. A 2004, 108:9423-9427.
58. Garau C., Quiñonero D., Frontera A., Ballester P., Costa A., Deyà P.M. New J. Chem. 2003, 27:211-214.
59. Quiñonero D., Frontera A., Garau C., Ballester P., Costa A., Deyà P.M. Chem. Phys. Chem. 2006, 7:2487-2491.
60. Quiñonero D., Frontera A., Deyà P.M. Chem. Phys. Chem. 2008, 9:397-399.
61. Gural'skiy I.A., Escudero D., Frontera A., Solntsev P.V., Rusanov E.B., Chernega A.N., Krautscheid H., Domasevitch K.V. Dalton Trans. 2009, 38:2856-2864.
62. Bauzá A., Quiñonero D., Deyà P.M., Frontera A. Theor. Chem. Acc. 2012, 131:1219-1230.
63. Estarellas C., Frontera A., Quiñonero D., Deyà P.M. J. Chem. Theory Comput. 2008, 4:1981-1989.
64. Quiñonero D., Frontera A., Escudero D., Ballester P., Costa A., Deyà P.M. Chem. Phys. Chem. 2007, 8:1182-1187.
65. Das A., Ray Choudhury S., Dey B., Yalamanchili S.K., Helliwell M., Gamez P., Mukhopadhyay S., Estarellas C., Frontera A. J. Phys. Chem. B 2010, 114:4998-5009.
66. Das A., Ray Choudhury S., Estarellas C., Dey B., Frontera A., Hemming J., Helliwell M., Gamez P., Mukhopadhyay S. Cryst. Eng. Comm. 2011, 13:4519-4527.
67. Fiol J.J., Barceló-Oliver M., Tasada A., Frontera A., Terrón à., García-Raso á. Coord. Chem. Rev. 2013, 10.1016/j.ccr.2012.12.013.
68. Chifotides H.T., Schottel B.L., Dunbar K.R. Angew. Chem. Int. Ed. 2010, 49:7202-7207.
69. Aragay G., Frontera A., Lloveras V., Vidal-Gancedo J., Ballester P. J. Am. Chem. Soc. 2013, 10.1021/ja309960m.
70. Gural'skiy I.A., Solntsev P.V., Krautscheid H., Domasevitch K.V. Chem. Commun. 2006, 42:4808-4810.
71. Escudero D., Frontera A., Quiñonero D., Deyà P.M. J. Comput. Chem. 2009, 2009(30):75-82.
72. Lucas X., Estarellas C., Escudero D., Frontera A., Quiñonero D., Deyà P.M. Chem. Phys. Chem 2009, 10:2256-2264.
73. Domasevitch K.V., Solntsev P.V., Gural'skiy I.A., Krautscheid H., Rusanov E.B., Chernega A.N., Howard J.A.K. Dalton Trans. 2007, 36:3893-3905.
74. Gural'skiy I.A., Solntsev P.V., Domasevitch K.V., Rusanov E.B., Chernega A.N. Acta Crystallogr. C 2007, 63:m259-m263.
75. Alkorta I., Blanco F., Elguero J., Estarellas C., Frontera A., Quiñonero D., Deyà P.M. J. Chem. Theory Comput. 2009, 5:1186-1194.
76. Alkorta I., Elguero J. J. Phys. Chem. A 2003, 107:9428-9433.
77. Quiñonero D., Frontera A., Deyà P.M., Alkorta I., Elguero J. Chem. Phys. Lett. 2008, 460:406-410.
78. Steed J.W., Juneja R.K., Atwood J.L. Angew. Chem. Int. Ed. Engl. 1994, 33:2456-2457.
79. Staffilani M., Bonvicini G., Steed J.W., Holman K.T., Atwood J.L., Elsegood M.R.J. Organometallics 1998, 17:1732-1740.
80. Staffilani M., Hancock K.S.B., Steed J.W., Holman K.T., Atwood J.L., Juneja R.K., Burkhalter R.S. J. Am. Chem. Soc. 1997, 119:6324-6335.
81. Holman K.T., Halihan M.M., Jurisson S.S., Atwood J.L., Burkhalter R.S., Mitchell A.R., Steed J.W. J. Am. Chem. Soc. 1996, 118:9567-9576.
82. Fairchild R.M., Holman K.T. J. Am. Chem. Soc. 2005, 127:16364-16365.
83. Sánchez Costa J., Gonzalez Castro A., Pievo R., Roubeau O., Modec B., Kozlevčar B., Teat S.J., Gamez P., Reedijk J. Cryst. Eng. Comm. 2010, 12:3057-3064.
84. White N.G., Kitchen J.A., Brooker S. Eur. J. Inorg. Chem. 2009, 1172-1180.
85. Brooker S., White N.G., Bauzá A., Deyà P.M., Frontera A. Inorg. Chem. 2012, 51:10334-10340.
86. Li Y., Huffman J.C., Flood A.H. Chem. Commun. 2007, 43:2692-2694.
87. Wei S., Li X., Yang Z., Lan J., Gao G., Xue Y., You J. Chem. Sci 2012, 3:359-363.
88. Senchyka G.A., Lysenkoa A.B., Naumovb D.Y., Fedinb V.P., Krautscheidc H., Domasevitch K.V. Inorg. Chem. Commun. 2010, 13:1576-1579.
89. de Hoog P., Gamez P., Mutikainen I., Turpeinen U., Reedijk J. Angew. Chem. Int. Ed. 2004, 43:5815-5817.
90. Zhou X.P., Zhang X.J., Lin S.H., Li D. Cryst. Growth Des. 2007, 7:485-489.
91. Schottel B.L., Chifotides H.T., Shatruk M., Chouai A., Perez L.M., Bacsa J., Dunbar K.R. J. Am. Chem. Soc. 2006, 128:5895-5912.
92. Campos-Fernández C.S., Schottel B.L., Chifotides H.T., Bera J.K., Bacsa J., Koomen J.M., Russell D.H., Dunbar K.R. J. Am. Chem. Soc. 2005, 127:12909-12923.
93. Black C.A., Hanton L.R., Spicer M.D. Chem. Commun. 2007, 43:3171-3173.
94. Galstyan A., Sanz Miguel P.J., Lippert B. Chem. Eur. J. 2010, 16:5577-5580.
95. Jose A.A., Kumar D.K., Ganguly B., Das A. Inorg. Chem. 2007, 46:5817-5819.
96. Arunachalam M., Ghosh P. Chem. Commun. 2009, 45:5389-5391.
97. Ortiz M.I., Soriano M.L., Carranza M.P., Jalón F.A., Steed J.W., Mereiter K., Rodríguez A.M., Quiñonero D., Deyà P.M., Manzano B.R. Inorg. Chem. 2010, 49:8828-8847.
98. Phuengphai P., Youngme S., Mutikainen I., Reedijk J. Inorg. Chem. Commun. 2012, 24:129-133.
99. Branzea D.G., Fihey A., Cauchy T., El-Ghayoury A., Avarvari N. Inorg. Chem. 2012, 51:8545-8556.
100. Lorcy D., Bellec N., Fourmigué M., Avarvari N. Coord. Chem. Rev. 2009, 253:1398-1438.
101. Shatruk M., Ray L. Dalton Trans. 2011, 39:11105-11121.
102. Qin L., Yao L.-Y., Yu S.-Y. Inorg. Chem. 2012, 51:2443-2453.
103. Chen K., Strasser C.E., Schmitt J.C., Shearer J., Catalano V.J. Inorg. Chem. 2012, 51:1207-1209.
104. D.T. Welideniya, C.B. Aakeroy, 47th Midwest Regional Meeting of the American Chemical Society, Omaha, NE, United States, October 24-27, 2012, MWRM-43.