Supramolecular effects involving the incorporation of guest substrates in imidazolium ionic liquid networks: Recent advances and future developments

Supramolecular Chemistry

Volumn 21, Issue 3-4, 2009, Pages 245-263

  Leclercq, Loïc ^a   Schmitzer, Andreea R ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

Host networks; Imidazolium salts; Inclusion complexes; Ionic liquids; Organic reactions

Indexed keywords

EID: 70349135752     PISSN: 10610278     EISSN: 10290478     Source Type: Journal    
DOI: 10.1080/10610270802468421     Document Type: Article

References (152)

1. Handy, S.T. Chem. Eur. J. 2003, 9, 2938-2944.
2. Holbrey, J.D.; Seddon, K.R. Clean Prod. Proc. 1999,1, 223-236.
3. Hagiwara, R.; Ito, Y. J. Fluor. Chem. 2000, 105, 221-232.
4. Scammells, P.J.; Scott, J.L.; Singer, R.D. Aust. J. Chem.2005, 58, 155-169.
5. Chiappe, C.; Pieraccini, D. J. Phys. Org. Chem. 2005,18, 275-297.
6. Holbrey, J.D.; Reichert, W.M.; Swatloski, R.P.; Broker, G.A., Pitner, W.R., Seddon, K.R., Rogers, R.D. GreenChem. 2002, 4, 407-413.
7. Brinchi, L.; Germani, R.; Savelli, G. Tetrahedron Lett.2003, 44, 2027-2029.
8. Cassol, C.C.; Ebeling, G.; Ferrera, B.; Dupont, J. Adv.Synth. Catal. 2006, 348, 243-248.
9. Zhao, H.; Malhotra, S.V. Aldrichimica. Acta 2002, 35,75-83.
10. Chauvin, Y.; Olivier-Bourbigou, H. Chemtech. 1995,25, 26-30.
11. Seddon, K.R. J. Chem. Technol. Biotechnol. 1997, 68,351-356.
12. Seddon, K.R. Chem. Commun. 2001, 2399-2407.
13. Baudequin, C.; Baudoux, J.; Levillain, J.; Cahard, D., Gaumont, A.C., Plaquevent, J.C. Tetrahedron: Asymm.2003, 14, 3081-3093.
14. Mehnert, C.P. Chem. Eur. J. 2005, 11, 50-56.
15. Blaser, H.-U.; Studer, M. Green Chem. 2003, 5, 112-117.
16. Song, C.E. Chem. Commun. 2004, 1033-1043.
17. Park, S.; Kazlauskas, R.J. Curr. Opin. Biotechnol. 2003,14, 432-437.
18. Kragl, U.; Eckstein, M.; Kaftzik, N. Curr. Opin.Biotechnol. 2002, 13, 565-571.
19. Poole, S.K.; Patel, S.; Dehring, K.; Workman, H.; Poole, C.F. J. Chromatogr. A, 2004, 1037, 445-454.
20. Stalcup, A.M.; Cabovska, B. J. Liq. Chromatogr. 2004,27, 1443-1459.
21. Antonietti, M.; Kuang, D.B.; Smarsly, B.; Yong, Z. Angew. Chem. Int. Ed. 2004, 4988-4992.
22. Geetha, S.; Trivedi, D.C. Bull. Electrochem. 2003, 19,37-48.
23. Dupont, J.; Suarez, P.A. Phys. Chem. Chem. Phys. 2006,8, 2441-2452.
24. Weingärtner, H. Angew. Chem. Int. Ed. 2008, 654-670.
25. Katritzky, A.R.; Jain, R.; Lomaka, A.; Petrukhin, R.;Karelson, M.; Visser, A.E.; Rogers, R.D. J. Chem. Inf.Comput. Sci. 2002, 42, 225-231.
26. Katritzky, A.R.; Lomaka, A.; Petrukhin, R.; Jain, R.; Karelson, M.; Visser, A.E.; Rogers, R.D. J. Chem. Inf.Comput. Sci. 2002, 42, 71-74.
27. Mandal, P.K.; Samanta, A. J. Phys. Chem. B 2005,109, 15172-15177.
28. Paul, A.; Mandal, P.K.; Samanta, A. Chem. Phys. Lett.2005, 402, 375-379.
29. Saha, S.; Mandal, P.K.; Samanta, A. Phys. Chem. Chem.Phys. 2004, 6, 3106-3110.
30. Fletcher, K.A.; Pandey, S. J. Phys. Chem. B, 2003,107, 13532-13539.
31. Fletcher, K.A.; Pandey, S. Appl. Spectrosc. 2002,56, 1498-1503.
32. Karmakar, R.; Samanta, A. J. Phys. Chem. A, 2002,106, 4447-4452.
33. Baker, S.N.; Baker, G.A.; Kane, M.A.; Bright, F.V. J. Phys. Chem. B, 2001, 105, 9663-9668.
34. Anderson, J.L.; Armstrong, D.W. Anal. Chem. 2003,75, 4851-4858.
35. Mandal, P.K.; Sarkar, M.; Samanta, A. J. Phys. Chem. A,2004, 108, 9048-9053.
36. Paul, A.; Mandal, P.K.; Samanta, A. J. Phys. Chem. B,2005, 109, 9148-9153.
37. Baker, S.N.; Baker, G.A.; Bright, F.V. Green Chem. 2002,4, 165-169.
38. Carmichael, A.J.; Seddon, K.R. J. Phys. Org. Chem. 2000,13, 591-595.
39. Crowhurst, L.; Mawdsley, P.R.; Perez-Arlandis, J.M.; Salter, P.A.; Welton, T. Phys. Chem. Chem. Phys. 2003,5, 2790-2794.
40. Cammarata, L.; Kazarian, S.G.; Salter, P.A.; Welton, T.Phys. Chem. Chem. Phys. 2001, 3, 5192-5200.
41. Chakraborty, N.; Chakraborty, A.; Seth, D.; Sarkar, N. J. Phys. Chem. A, 2005, 109, 1764-1769.
42. Quinn, B.M.; Ding, Z.F.; Moulton, R.; Bard, A. J. angmuir 2002, 18, 1734-1742.
43. Swiderski, K.; McLean, A.; Gordon, C.M.; Vaughan, D.H. Chem. Commun. 2004, 590-591.
44. Dupont, J.; Spencer, J. Angew. Chem. Int. Ed. 2004, 43, 5296-5297.
45. Dupont, J. J. Braz. Chem. Soc. 2004, 15, 341-350.
46. Gozzo, F.C.; Santos, L.S.; Augusti, R.; Consorti, C.S.; Dupont, J.; Eberlin, M.N. Chem. Eur. J. 2004, 10,6187-6193.
47. Rovere, M.; Tosi, M.P. Rep. Prog. Phys. 1986, 49,1001-1081.
48. Biggin, S.; Enderby, J.E. J. Chem. Phys. 1982, 15,L305-L307.
49. Cang, H.; Li, J.; Fayer, M.D. J. Chem. Phys. 2003,119, 13017-13023.
50. Dieter, K.M.; Dymek, C.J.J.; Heimer, N.E.; Rovang, J.W.; Wilkes, J.S. J. Am. Chem. Soc. 1988, 110, 2722-2726.
51. Suarez, A.Z.; Einloft, S.; Dullius, J.E.L.; Souza, R.F.d.; Dupont, J. J. Chim. Phys. Phys. Chim. Biol. 1998,95, 1626-1639.
52. Ozawa, R.; Hayashi, S.; Saha, S.; Kobayashi, A.; Hamaguchi, H. Chem. Lett. 2003, 32, 948-949.
53. Talaty, E.R.; Raja, S.; Storhaug, V.J.; Dolle, A.; Carper, W.R. J. Phys. Chem. B 2004, 108, 13177-13184.
54. Hardacre, C.; Holbrey, J.D.; McMath, S.E.J.; Bowron, D.T.; Soper, A.K. J. Chem. Phys. 2003, 118, 273-278.
55. Bradley, A.E.; Hardacre, C.; Holbrey, J.D.; Johnston, S.; McMath, S.E.J.; Nieuwenhuyzen, M. Chem. Mater. 2002,14, 629-635.
56. Carmichael, A.J.; Hardacre, C.; Holbrey, J.D.; Nieuwenhuyzen, M.; Seddon, K.R. J. Mol. Phys. 2001,99, 795-800.
57. Dupont, J.; Suarez, P.A.; De Souza, R.F.; Burrow, R.A.; Kintzinger, J.P. Chem. Eur. J. 2000, 6, 2377-2381.
58. Antony, J.H.; Mertens, D.; Dolle, A.; Wasserscheid, P.;Carper, W.R. Chem. Phys. Chem. 2003, 4, 588-594.
59. Heimer, N.E.; Del Sesto, R.E.; Carper, W.R. Magn. Reson.Chem. 2004, 42, 71-75.
60. Mele, A.; Tran, C.D.; Lacerda, S.H.D. Angew. Chem. Int.Ed. 2003, 4364-4366.
61. Mele, A.; Romano, G.; Giannone, M.; Ragg, E.; Fronza, G.; Raos, G.; Marcon, V. Angew. Chem. Int. Ed. 2006, 45, 1123-1126.
62. Dyson, P.J.; Khalaila, I.; Luettgen, S.; McIndoe, J.S.; Zhao, D.B. Chem. Commun. 2004, 2204-2205.
63. Consorti, C.S.; Suarez, P.A.; de Souza, R.F.; Burrow, R.A.; Farrar, D.H.; Lough, A.J.; Loh, W.; da Silva, L.H.; Dupont, J. J. Phys. Chem. B 2005, 109, 4341-4349.
64. Leclercq, L.; Schmitzer, A.R. J. Phys. Chem. A 2008,112, 4996-5001.
65. Suisse, J.-M.; Douce, L.; Bellemin-Laponnaz, S.; Maisse-François, A.; Welter, R.; Miyake, Y.; Shimizu, Y. Eur.J. Inorg. Chem. 2007, 3899-3905.
66. Hansen, J.P.; McDonald, I.R. Theory of Simple Liquids, 2nd ed.; Academic Press: London, 1986.
67. Hansen, J.P.; McDonald, I.R. Phys. Rev. A 1975, 11, 2111-2123.
68. Gordon, C.M.; Holbrey, J.D.; Kennedy, A.R.; Seddon, K.R. J. Mater. Chem. 1998, 8, 2627-2636.
69. Scröder, U.; Wadhawan, J.D.; Compton, R.G.; Marken, F.; Suarez, P.A.Z.; Consorti, C.S.; de Souza, R.F.; Dupont, J. New J. Chem. 2000, 24, 1009-1015.
70. Canongia Lopes, J.N.; Costa Gomes, M.F.; Padua, A.A. J. Phys. Chem. B 2006, 110, 16816-16818.
71. Holbrey, J.D.; Reichert, W.M.; Tkatchenko, I.; Bouajila, E.; Walter, O.; Tommasi, I.; Rogers, R.D. Chem. Commun.2003, 28-29.
72. Deetlefs, M.; Seddon, K.R.; Shara, M. Phys. Chem. Chem.Phys. 2006, 8, 642-649.
73. Hanke, C.G.; Lynden-Bell, R.M. J. Phys. Chem. B 2003,107, 10873-10878.
74. Bowron, D.T.; Finney, J.L.; Soper, A.K. J. Phys. Chem. B 1998, 102, 3551-3563.
75. Cassol, C.C.; Umpierre, A.P.; Ebeling, G.; Ferrera, B.; Chiaro, S.S.X.; Dupont, J. Int. J. Mol. Sci. 2007, 8,593-605.
76. Leclercq, L.; Suisse, I.; Nowogrocki, G.; Agbossou-Niedercorn, F. Green Chem. 2007, 9, 1097-1103.
77. Lozano, P.; de Diego, T.; Gmouh, S.; Vaultier, M.; Iborra, J.L. Biotechnol. Prog. 2004, 20, 661-669.
78. Okochi, M.; Nakagawa, I.; Kobayashi, T.; Hayashi, S.; Furusaki, S.; Honda, H. J. Biotech. 2007, 128, 376-382.
79. Machado, M.F.; Saraiva, J.M. Biotechnol. Lett. 2005,27, 1233-1239.
80. Feher, E.; Major, B.; Belafi-Bako, K.; Gubicza, L. Biochem. Soc. Trans. 2007, 35, 1624-1629.
81. Machado, G.; Scholten, J.D.; Vargas, T.d.; Teixeira, S.R.; Ronchi, L.H.; Dupont, J. Int. J. Nanotech. 2007, 4,541-563.
82. Migowski, P.; Machado, G.; Texeira, S.R.; Alves, M.C.; Morais, J.; Traverse, A.; Dupont, J. Phys. Chem. Chem.Phys. 2007, 9, 4814-4821.
83. Clavel, G.; Larionova, J.; Guari, Y.; Guerin, C. Chem. Eur.J. 2006, 12, 3798-3804.
84. Meiss, S.A.; Rohnke, M.; Kienle, L.; Abedin, S.Z.E.; Endres, F.; Janek, J. Chem. Phys. Chem. 2007, 50-53.
85. Abedin, S.Z.E.; Moustafa, E.M.; Hempelmann, R.; Natter, H.; Endres, F. Chem. Phys. Chem. 2006, 1535.
86. Abedin, S.Z.E.; Moustafa, E.M.; Hempelmann, R.; Natter, H.; Endres, F. Electrochem. Commun. 2005, 1111-1116.
87. Gutel, T.; Garcia-Anton, J.; Pelzer, K.; Philippot, K.; Santini, C.C.; Chauvin, Y.; Chaudret, B.; Basset, J.-M. J. Mat. Chem. 2007, 3290-3292.
88. Silveira, E.T.; Umpierre, A.P.; Rossi, L.M.; Machado, G.; Morais, J.; Soares, G.V.; Baumvol, I.J.; Teixeira, S.R.; Fichtner, P.F.; Dupont, J. Chem. Eur. J. 2004, 10,3734-3740.
89. Rossi, L.M.; Machado, G.; Fichtner, P.F.P.; Teixeira, S.R.; Dupont, J. Catal. Lett. 2004, 92, 149-155.
90. Cassol, C.C.; Umpierre, A.P.; Machado, G.; Wolke, S.I.; Dupont, J. J. Am. Chem. Soc. 2005, 127, 3298-3299.
91. Calo, I.; Nacci, A.; Monopoli, A.; Detomaso, A.; Iliade, P. Organomet. 2003, 4193-4197.
92. Gelesky, M.A.; Umpierre, A.P.; Machado, G.; Correia, R.R.; Magno, W.C.; Morais, J.; Ebeling, G.; Dupont, J. J. Am. Chem. Soc. 2005, 127, 4588-4589.
93. Wittkopp, A.; Schreiner, P.R. Catalysis of Diels-AlderReactions in Water and in Hydrogen Bonding Environments;Wiley-Interscience: Chichester, 2000.
94. Otto, S.; Engberts, J.B.F.N. Pure Appl. Chem. 2000,72, 1365-1372.
95. Blake, J.F.; Jorgensen, W.L. J. Am. Chem. Soc. 1991,113, 7430-7432.
96. Blake, J.F.; Lim, D.; Jorgensen, W.L. J. Org. Chem. 1994,59, 803-805.
97. Etter, M.C. Acc. Chem. Res. 1990, 23, 120-126.
98. Fischer, T.; Sethi, A.; Welton, T.; Woolf, J. TetrahedronLett. 1999, 40, 793-796.
99. Earle, M.J.; McCormac, P.B.; Seddon, K.R. Green Chem.1999, 1, 517-520.
100. Ludley, P.; Karodia, N. Tetrahedron Lett. 2001, 42,2011-2014.
101. Dzyuba, S.V.; Bartsch, R.A. Tetrahedron Lett. 2002,43, 4657-4659.
102. Dubreuil, J.F.; Bazureau, J.P. Tetrahedron Lett. 2000,41, 7351-7355.
103. Aggarwal, A.; Lancaster, N.L.; Sethi, A.R.; Welton, T. Green Chem. 2002, 4, 517-520.
104. Janus, E.; Goc-Maciejewska, I.; Lozynski, M.; Pernak, J. Tetrahedron Lett. 2006, 47, 4079-4083.
105. Bravo, J.L.; Lopez, I.; Cintas, P.; Silvero, G.; Arevalo, M.J. Ultrason. Sonochem. 2006, 13, 408-414.
106. Gmeiner, G.; Reichel, C.; Lendl, B.; Gaertner, P. Synthesis 2007, 9, 1333-1338.
107. Gholap, A.R.; Venkatesan, K.; Daniel, T.; Lahoti, R.J.; Srinivasan, K.V. Green Chem. 2003, 5, 693-696.
108. Fraga-Dubreuil, J.; Bourahla, K.; Rahmouni, M.; Bazureau, J.-P.; Hamelin, J. Catal. Commun. 2002, 3, 185-190.
109. Gholap, A.R.; Venkatesan, K.; Daniel, T.; Lahoti, R.J.; Srinivasan, K.V. Green Chem. 2004, 6, 147-150.
110. Adams, C.J.; Earle, M.J.; Roberts, G.; Seddon, K.R. Chem.Commun. 1998, 2097-2098.
111. Boon, J.A.; Levisky, J.A.; Pflug, J.L.; Wilkes, J.S. J. Org.Chem. 1986, 51, 480-483.
112. Csihony, S.; Mehdi, H.; Horvath, I.T. Green Chem. 2001, 3, 307-309.
113. Avent, A.G.; Chaloner, P.A.; Day, M.P.; Seddon, K.R.; Welton, T. J. Chem. Soc. Dalton Trans. 1994, 3405-3413.
114. Nara, S.J.; Harjani, J.R.; Salunkhe, M.M. J. Org. Chem.2001, 66, 8616-8620.
115. Earle, M.J.; Katdare, S.P.; Seddon, K.R. Org. Lett. 2004,6, 707-710.
116. Basavaiah, D.; Rao, P.D.; Hyma, R.S. Tetrahedron 1996,52, 8001-8062.
117. Ameer, F.; Drewes, S.E.; Freese, S.; Kaye, P.T. Synth.Commun. 1988, 18, 495-500.
118. Dieter, K.M.; Dymek, C.J.; Heimer, N.E.; Rovang, J.W.; Wilkes, J.S. J. Am. Chem. Soc. 1988, 110, 2722-2726.
119. Santos, L.S.; Neto, B.A.D.; Consorti, C.S.; Pavam, C.H.; Almeida, W.P.; Coelho, F.; Dupont, J.; Eberlin, M.N. J. Phys. Org. Chem. 2006, 19, 731-736.
120. Lancaster, N.L.; Welton, T. J. Org. Chem. 2004, 69,5986-5992.
121. Lancaster, N.L.; Welton, T.; Young, G.B. J. Chem. Soc., Perkin Trans. 2 2001, 2267-2270.
122. Lancaster, N.L.; Salter, P.A.; Welton, T.; Young, G.B. J. Org. Chem. 2002, 67, 8855-8861.
123. Chiappe, C.; Pieraccini, D. J. Org. Chem. 2004, 69,6059-6064.
124. Ross, J.; Xiao, J. Chem. Eur. J. 2003, 9, 4900-4906.
125. Chiappe, C.; Leandri, E.; Pieraccini, D. Chem. Commun.2004, 2536-2537.
126. Chowdhury, S.; Mohan, R.S.; Scott, J.L. Tetrahedron 2007, 63, 2363-2389.
127. Ranu, B.C.; Banerjee, S. J. Org. Chem. 2005, 70,4517-4519.
128. House, H.O. J. Am. Chem. Soc. 1955, 77, 3070-3075.
129. Kim, Y.J.; Varma, R.S. J. Org. Chem. 2005, 70, 7882-7891.
130. Kim, H.S.; Kim, J.J.; Kim, H.; Jang, H.G. J. Catal. 2003,220, 44-46.
131. Sun, J.; Fujita, S.; Zhao, F.; Arai, M. Green Chem. 2004,6, 613-616.
132. de Bellefon, C.; Pollet, E.; Grenouillet, P. J. Mol. Catal.1999, 1247-1248.
133. Chen, W.; Xu, L.; Chatterton, C.; Xiao, J. Chem. Commun.1999, 1247-1248.
134. Ross, J.; Chen, W.; Xu, L.; Xiao, J. Organomet. 2001,20, 138-142.
135. Reichardt, C. Solvents and Solvent Effects in OrganicChemistry, 2nd ed.; 1988.
136. Leclercq, L.; Suisse, I.; Agbossou-Niedercorn, F. J. Mol.Struct. 2008, 892, 433-437.
137. Schulz, P.S.; Muller, N.; Bosmann, A.S.; Wasserscheid, P. Angew. Chem. Int. Ed. 2007, 46, 1293-1295.
138. Wasserscheid, P.; Driessen-Hoelscher, B.; Hal, R.v.; Steffens, H.C.; Zimmermann, J. Chem. Commun. 2003,2038-2039.
139. Leclercq, L.; Suisse, I.; Agbossou-Niedercorn, F. Chem.Commun. 2008, 311-313.
140. Sieffert, N.; Wipff, G. J. Phys. Chem. B 2007, 111,4951-4962.
141. Chauvin, Y.; Mussmann, L.; Olivier, H. Angew. Chem.,Int. Ed. 1995, 34, 2698-2700.
142. Waffenschmidt, H.; Wasserscheid, P. J. Mol. Catal. A:Chem. 2000, 164, 61-67.
143. Brasse, C.C.; Englert, U.; Salzer, A.; Waffenschmidt, H.; Wasserscheid, P. Organomet. 2000, 19, 3818-3823.
144. Wasserscheid, P.; Waffenschmidt, H.; Machnitzki, P.; Kottsieper, K.W.; Stielzer, O. Chem. Commun. 2001,451-452.
145. Keim, W.; Vogt, D.; Waffenschmidt, H.; Wasserscheid, P. J. Catal. 1999, 186, 481-484.
146. Sellin, M.F.; Webb, P.B.; Cole-Hamilton, D. J. Chem.Commun. 2001, 781-782.
147. Siddiqui, S.A.; Narkhede, U.C.; Palimkar, S.S.; Daniel, T.; Lahoti, R.J.; Srinivasan, K.V. Tetrahedron 2005, 61,3539-3546.
148. Morrison, D.W.; Forbesa, D.C.; Davis, J.H., Jr. TetrahedronLett. 2001, 42, 6053-6055.
149. Seddon, K.R.; Stark, A.; Torres, M.-J. Pure Appl. Chem.2000, 72, 2275-2287.
150. Crosthwaite, J.M.; Aki, S.N.V.K.; Maginn, E.J.; Brennecke, J.F. Fluid Ph. Equil. 2005, 228 and 303.
151. Yoon, J.; Kim, S.K.; Singh, N.J.; Kim, K.S. Chem. Soc.Rev. 2006, 35, 355-360.
152. Gutowski, K.E.; Broker, G.A.; Willauer, H.D.; Huddleston, J.G.; Swatloski, R.P.; Holbrey, J.D.; Rogers, R.D. J. Am. Chem. Soc. 2003, 125, 6632-6633.